7 events found.
Ongoing
Karaoke w/ Jason at Rick’s Bar Downstairs Stage
Rick's Entertainment Complex 202 Duval Street, Key West
Free
Yoga on the Beach – Ft Zachary Taylor
Fort Zachary Taylor State Park 601 Howard England Way, Key West
$20
Lance Taylor at Two Friends Patio Restaurant
Two Friends Patio Restaurant 512 Front Street, Key West
Free
Distillery Tour – Key West Legal Rum Distillery
Key West First Legal Rum Distillery 107 Simonton Street, Key West
Free
Mojito Class by Key West Legal Rum Distillery – Min 4 people
Key West First Legal Rum Distillery 107 Simonton Street, Key West
$75.00
Glass Bottom Boat Cruise – Key West’s Window to the Sea
Fury Key West- Departure Point 2 0 Duval St, Key West
$69.95
Webb Dillard at Rick’s Bar Downstairs Stage
Rick's Entertainment Complex 202 Duval Street, Key West
Free
Rick Fusco at Two Friends Patio Restaurant
Two Friends Patio Restaurant 512 Front Street, Key West
Free
Glass Bottom Boat Cruise – Key West’s Window to the Sea
Fury Key West- Departure Point 2 0 Duval St, Key West
$69.95
Reef Snorkeling, Dolphin Watch Eco Tour & Sunset Cruise
Sunset Watersports - 201 Williams St 201 William Street, Key West
$79.95
Just George at Rick’s Bar Downstairs Stage
Rick's Entertainment Complex 202 Duval Street, Key West
Free
Glass Bottom Boat Cruise – Key West’s Window to the Sea
Fury Key West- Departure Point 2 0 Duval St, Key West
$69.95
Caribe of Key West at El Meson de Pepes on Mallory Square
El Meson De Pepes Restaurant and Bar 410 Wall Street, Key West
CW Colt at Two Friends Patio Restaurant
Two Friends Patio Restaurant 512 Front Street, Key West
Free
Lary Smith Jazz Jam at William Weech American Legion Post 168
William Weech American Legion Post 168 803 Emma Street, Key West
Free
Week of Events
DJ Marty at Red Garter Saloon Stage
DJ Marty, known for his electrifying performances and seamless mixing skills, takes center stage at Red Garter Saloon. With his dynamic energy and innovative approach…
Free
DJ Kori at Rick’s Bar Upstairs Stage
Experience the electrifying beats of DJ Kori at Rick's Bar Upstairs Stage. Renowned for transforming events into unforgettable celebrations, DJ Kori boasts an extensive music…
Free
Durtbags at Durty Harry’s Stage
Experience the electrifying energy of The Durtbags at Durty Harry's Stage in Key West. As the ultimate party rock band, they deliver unforgettable performances every…
Free
Matthew Curry Band at Hog’s Breath Saloon
The Matthew Curry Band delivers electrifying performances at Hog's Breath Saloon, showcasing Matthew Curry's exceptional guitar skills and emotive vocals. Known for their dynamic blend…
Free
Karaoke at Bobby’s Monkey Bar
Experience a lively island atmosphere at Bobby's Monkey Bar in Key West's Old Town, where karaoke nights shine with vibrant entertainment. The charismatic performers create…
Mylo O’Maolain at Irish Kevin’s Bar
Mylo O’Maolain captivates audiences at Irish Kevin’s Bar with his vibrant performances in the heart of Old Town Key West. Delivering lively music that perfectly…
Free
Turning The Tide at Sloppy Joe’s Bar
Turning The Tide at Sloppy Joe's Bar features an inspiring performance by Turning The Tide, focusing on resilience and determination. Their narrative weaves themes of…
Free
Karaoke w/ Jason at Rick’s Bar Downstairs Stage
Join DJ Jason at Rick's Bar Downstairs Stage for an electrifying karaoke night. Known for his dynamic style and ability to energize crowds, Jason seamlessly…
Free
Martini Monday at Virgilios
Experience Martini Monday at Virgilio’s in Old Town Key West, where you can savor exquisite martinis and enjoy live performances every evening. This stylish lounge…
Free
DJ Marty at Red Garter Saloon Stage
DJ Marty, an innovative music curator, transforms the Red Garter Saloon Stage into an electrifying nightlife experience. Known for his seamless mixing skills and vibrant…
Free
DJ Duke at Rick’s Bar Upstairs Stage
DJ Duke delivers an electrifying performance at Rick's Bar Upstairs Stage. Known for his dynamic music production and mesmerizing mixes, his vibrant stage presence captivates…
Free
HYPER DRIVE at Durty Harry’s Stage
Experience the electrifying talent of Hyper Drive at Durty Harry's Stage, where his dynamic performances as a vocalist, guitarist, songwriter, and producer take center stage.…
Free
Homegrown at Hog’s Breath Saloon
Experience the vibrant sounds of Homegrown at Hog's Breath Saloon, a dynamic country band from Key West, Florida. With heartfelt lyrics and captivating melodies, they…
Free
Karaoke at Bobby’s Monkey Bar
Join the charismatic and talented performer at Bobby's Monkey Bar for an unforgettable night of karaoke in Key West's Old Town. The lively island atmosphere…
Mylo O’Maolain at Irish Kevin’s Bar
Mylo O’Maolain delivers electrifying performances at Irish Kevin’s Bar, engaging audiences with his dynamic stage presence and captivating music. Known for creating an interactive and…
Free
Turning The Tide at Sloppy Joe’s Bar
Turning The Tide takes center stage at Sloppy Joe's Bar, weaving a compelling narrative about resilience and determination. Against a lively backdrop, this enthralling performance…
Free
DJ Todd at Red Garter Saloon Stage
Experience the electrifying beats of DJ Todd at the Red Garter Saloon Stage. Known for his innovative and dynamic performances, DJ Todd captivates audiences with…
Free
DJ Duke at Rick’s Bar Upstairs Stage
Experience the electrifying energy of DJ Duke at Rick's Bar Upstairs Stage. Renowned for his dynamic mixes and vibrant performances, DJ Duke captivates audiences with…
Free
Homegrown at Hog’s Breath Saloon
Experience the vibrant sounds of Homegrown at Hog's Breath Saloon, a dynamic country band from Key West, Florida. With heartfelt lyrics and captivating melodies, they…
Free
Karaoke at Bobby’s Monkey Bar
Enjoy a vibrant evening at Bobby's Monkey Bar, nestled in Key West's Old Town. This lively venue offers karaoke nightly, featuring charismatic entertainers who engage…
Tim Bradach at Irish Kevin’s Bar
Tim Bradach captivates audiences at Irish Kevin’s Bar with his energetic performances and musical talent. Known for engaging the crowd, Tim creates an unforgettable night…
Free
Turning The Tide at Sloppy Joe’s Bar
Experience the remarkable journey of Turning The Tide at Sloppy Joe's Bar. This event showcases the entertainer's narrative mastery as they explore themes of resilience…
Free
Wednesday Filet Day at Mary Ellen’s
Join the lively atmosphere at Mary Ellen's in Old Town Key West for Wednesday Filet Day. Enjoy classic American comfort food, including mouthwatering gourmet grilled…
Free
DJ Todd at Red Garter Saloon Stage
Experience the electrifying talents of DJ Todd at the Red Garter Saloon Stage. Known for his innovative mixes and dynamic performances, DJ Todd captivates audiences…
Free
DJ Duke at Rick’s Bar Upstairs Stage
Experience the electrifying beats of DJ Duke at Rick's Bar Upstairs Stage. Renowned for his dynamic and innovative music production, DJ Duke captivates global audiences…
Free
Crank Sinatra at Durty Harry’s Stage
Experience the electrifying energy of Krank Sinatra, a multi-talented musician in Key West, at Durty Harry's Stage. Known for his dynamic performances, Krank Sinatra captivates…
Free
Homegrown at Hog’s Breath Saloon
Experience the vibrant sounds of Homegrown at Hog's Breath Saloon, a dynamic country band from Key West, Florida. With heartfelt lyrics and captivating melodies, they…
Free
Karaoke at Bobby’s Monkey Bar
Enjoy an unforgettable evening at Bobby's Monkey Bar, where the charismatic karaoke host steals the show. With their energetic presence, they turn every night into…
Tim Bradach at Irish Kevin’s Bar
Tim Bradach captivates audiences at Irish Kevin's Bar with his engaging performances. Known for his dynamic presence, he seamlessly blends a variety of musical genres,…
Free
Turning The Tide at Sloppy Joe’s Bar
Experience the captivating narrative of Turning The Tide at Sloppy Joe's Bar in Key West. This inspiring storyteller takes you on a transformative journey of…
Free
Karaoke w/ Davis at Rick’s Bar Downstairs Stage
Join the electrifying DJ Davis for an unforgettable night of karaoke at Rick's Bar Downstairs Stage. Known for his eclectic mix and infectious energy, Davis…
Free
DJ Marty at Red Garter Saloon Stage
Experience the electrifying energy of DJ Marty at the Red Garter Saloon Stage. Known for his dynamic mixing skills and innovative music curation, DJ Marty…
Free
DJ Chaka at Rick’s Bar Upstairs Stage
Experience the dynamic beats of DJ Chaka at Rick's Bar Upstairs Stage in Key West. A lively entrepreneur and cancer survivor, DJ Chaka channels his…
Free
Durtbags at Durty Harry’s Stage
Experience the ultimate party with The Durtbags, Key West's premier rock band, at Durty Harry's Stage. Performing live every Thursday through Sunday, their energetic shows…
Free
Karaoke with Foss at RockHouse Live
Join Foss for an electrifying night of karaoke at RockHouse Live in Key West. Known for his dynamic stage presence, Foss elevates the karaoke experience,…
Free
Elle Haley & the Why Nots at General Horseplay
Elle Haley, a vibrant musician from the Florida Keys, brings her captivating performances to General Horseplay. Known for soulful tunes, Elle offers audiences a musical…
Free
Homegrown at Hog’s Breath Saloon
Homegrown is a dynamic country band originating from Key West, Florida, captivating audiences with heartfelt lyrics and engaging melodies. Performing live at Hog's Breath Saloon,…
Free
Karaoke at Bobby’s Monkey Bar
Enjoy electrifying evenings with top-notch entertainers at Bobby's Monkey Bar's karaoke nights. Nestled in Key West's Old Town, the bar boasts a lively island atmosphere…
Turning The Tide at Sloppy Joe’s Bar
At Sloppy Joe's Bar, Turning The Tide captivates audiences with a powerful narrative of resilience and determination. This transformative performance explores personal and social challenges,…
Free
Tim Bradach at Irish Kevin’s Bar
Experience the vibrant energy of Tim Bradach at Irish Kevin's Bar, where his captivating performances bring the venue to life. As a talented musician, Tim…
Free
Karaoke w/ Jason at Rick’s Bar Downstairs Stage
Join DJ Jason at Rick's Bar Downstairs Stage for an unforgettable karaoke night. Renowned for his electrifying beats and seamless mixing, Jason captivates audiences with…
Free
DEAD FEST KEY WEST – April 17, 18, 19 – 2026
Join us for DEAD FEST KEY WEST 2026, a thrilling free festival celebrating the Grateful Dead's legacy. Headlined by the electrifying STEELY DEAD, the event…
Free
DJ Marty at Red Garter Saloon Stage
DJ Marty electrifies the Red Garter Saloon Stage at Rick's Entertainment Complex with his dynamic music curation and seamless mixing skills. Renowned for his vibrant…
Free
DJ Duke at Rick’s Bar Upstairs Stage
DJ Duke is a dynamic music producer renowned for his electrifying performances and mesmerizing mixes. Known for his vibrant stage presence, he expertly blends genres,…
Free
Durtbags at Durty Harry’s Stage
Experience the ultimate party atmosphere with The Durtbags, Key West's premier party rock band, at Durty Harry's stage in Rick's Entertainment Complex. Known for their…
Free
Homegrown at Hog’s Breath Saloon
Experience the vibrant sounds of Homegrown at Hog's Breath Saloon, a dynamic country band from Key West, Florida. With heartfelt lyrics and captivating melodies, they…
Free
Karaoke at Bobby’s Monkey Bar
Experience unforgettable evenings at Bobby's Monkey Bar in Key West, where a dynamic entertainer leads karaoke nights, transforming the lively island atmosphere into a vibrant…
DJ Sanaris at Tiki House Key West
DJ Sanaris, the owner of Pulse Groovz LLC, brings electrifying energy to Tiki House Key West. With a reputation for creating a fun, lively atmosphere,…
Free
Turning The Tide at Sloppy Joe’s Bar
Turning The Tide at Sloppy Joe's Bar showcases an inspiring performance centered on resilience and determination. Set against thrilling live music, the entertainer captivates audiences…
Free
Riptide Riot at Irish Kevin’s Bar
Experience the electrifying performance of Riptide Riot, a dynamic power duo from Key West, at Irish Kevin's Bar. Featuring Jim Simonian and Tim Bradach, they…
Free
Karaoke w/ Jason at Rick’s Bar Downstairs Stage
Join DJ Jason at Rick's Bar Downstairs Stage as he transforms karaoke into an electrifying experience. Known for his dynamic beats and seamless mixes, Jason…
Free
DJ Marty at Red Garter Saloon Stage
DJ Marty is a dynamic and innovative music curator renowned for his electrifying performances at the Red Garter Saloon Stage. His seamless mixing skills and…
Free
DJ Chaka at Rick’s Bar Upstairs Stage
Experience the electrifying beats of DJ Chaka at Rick's Bar Upstairs Stage. A Key West icon, DJ Chaka infuses his sets with energy and passion,…
Free
Durtbags at Durty Harry’s Stage
Experience the electrifying performances of The Durtbags at Durty Harry's Stage in Key West's Rick's Entertainment Complex. Known as the ultimate party rock band, they…
Free
The Tiki Bombs at Tiki House Key West
The Tiki Bombs are a dynamic band renowned for their electrifying performances and tropical-inspired sound. Merging traditional island melodies with modern rock, they deliver a…
Free
Homegrown at Hog’s Breath Saloon
Experience the vibrant sounds of Homegrown at Hog's Breath Saloon, a dynamic country band from Key West, Florida. With heartfelt lyrics and captivating melodies, they…
Free
Karaoke at Bobby’s Monkey Bar
Experience a night of vibrant entertainment at Bobby's Monkey Bar in Key West's Old Town, where the star of the show is the charismatic karaoke…
Radio Hero at Sloppy Joe’s Bar
Experience the electrifying energy of Radio Hero at Sloppy Joe's Bar in Key West. Known for their bold stage presence and dynamic sound, this edgy…
Free
Jack Wolf at Irish Kevin’s Bar
Jack Wolf, a talented singer-songwriter based in Key West, captivates audiences at Irish Kevin's Bar with his soulful performances. Known for his passionate melodies and…
Free
Karaoke w/ Jason at Rick’s Bar Downstairs Stage
Experience an unforgettable evening with DJ Jason at Rick's Bar Downstairs Stage in Key West. Known for his electrifying beats and ability to read the…
Free
DJ Marty at Red Garter Saloon Stage
Experience the electrifying energy of DJ Marty at the Red Garter Saloon Stage in Key West's Rick's Entertainment Complex. Renowned for his seamless mixing and…
Free
Homegrown at Hog’s Breath Saloon
Homegrown is a dynamic country band from Key West, celebrated for their heartfelt lyrics and captivating melodies. Performing at Hog's Breath Saloon, they offer a…
Free
Karaoke at Bobby’s Monkey Bar
Experience an unforgettable evening at Bobby's Monkey Bar with dynamic karaoke sessions led by an engaging and talented entertainer. Nestled in Key West's Old Town,…
Mylo O’Maolain at Irish Kevin’s Bar
Experience the charismatic Mylo O'Maolain captivating audiences at Irish Kevin's Bar in Key West. Known for his vibrant performances, Mylo brings infectious energy and musical…
Free
Radio Hero at Sloppy Joe’s Bar
Experience the electrifying energy of Radio Hero at Sloppy Joe's Bar, where this edgy party rock band delivers high-octane performances that captivate audiences. Known for…
Free
Monday, April 13, 2026
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April 13, 2026 -Fishmonster Max- Daily Party Boat Fishing
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April 13, 2026 -Yoga on the Beach – Ft Zachary Taylor
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April 13, 2026 -Aqua Yoga at Southernmost Beach Resort
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April 13, 2026 -Lance Taylor at Two Friends Patio Restaurant
-
April 13, 2026 -Rolando Rojas at Sloppy Joe’s Bar
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April 13, 2026 -Distillery Tour – Key West Legal Rum Distillery
-
April 13, 2026 -Mojito Class by Key West Legal Rum Distillery – Min 4 people
-
April 13, 2026 -Bradd Shadduck at Irish Kevin’s Bar
-
April 13, 2026 -Nick Norman at Rams Head Southernmost
-
April 13, 2026 -Glass Bottom Boat Cruise – Key West’s Window to the Sea
-
April 13, 2026 -Tim Hollohan at Sloppy Joe’s Bar
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April 13, 2026 -Jay Klein at Schooner Wharf Bar
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April 13, 2026 -Zack Seemiller at Hog’s Breath Saloon
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April 13, 2026 -Webb Dillard at Rick’s Bar Downstairs Stage
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April 13, 2026 -Tom Curtis Jr at Hank’s Hair of the Dog Saloon
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April 13, 2026 -Rick Fusco at Two Friends Patio Restaurant
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April 13, 2026 -Glass Bottom Boat Cruise – Key West’s Window to the Sea
-
April 13, 2026 -Jon Hollywood at Tiki House Key West
-
April 13, 2026 -Oren Polak at Irish Kevin’s Bar
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April 13, 2026 -Reef Snorkeling, Dolphin Watch Eco Tour & Sunset Cruise
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April 13, 2026 -Just George at Rick’s Bar Downstairs Stage
-
April 13, 2026 -Glass Bottom Boat Cruise – Key West’s Window to the Sea
-
April 13, 2026 -Cliff Cody at Mac’s Place
-
April 13, 2026 -Telephone Tag at Hog’s Breath Saloon
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April 13, 2026 -Glow Hours on Hugh’s View
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April 13, 2026 -Caribe of Key West at El Meson de Pepes on Mallory Square
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April 13, 2026 -Sunset Celebration at Mallory Square
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April 13, 2026 -Scott Morlock at Hank’s Hair of the Dog Saloon
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April 13, 2026 -Tony Roberts at Rams Head Southernmost
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April 13, 2026 -World Famous 801 Girls- 5pm Show
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April 13, 2026 -CW Colt at Two Friends Patio Restaurant
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April 13, 2026 -Pete & Larry Sloppy 2nds at Sloppy Joe’s Bar
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April 13, 2026 -NY Pauly at Irish Kevin’s Bar
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April 13, 2026 -Barrett Thomas at The Alamo Key West
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April 13, 2026 -Magic The Gathering Night at The Retro Room
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April 13, 2026 -Charity Bingo at The Green Parrot
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April 13, 2026 -Joe The Show at Schooner Wharf Bar
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April 13, 2026 -Lary Smith Jazz Jam at William Weech American Legion Post 168
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April 13, 2026 -Charles Miller at Rick’s Bar Downstairs Stage
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April 13, 2026 -Gastor Almonte at Comedy Key West
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April 13, 2026 -Jefff Clark at Tiki House Key West
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April 13, 2026 -Elle Haley at Halo Rooftop Lounge Bar at The Saint
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April 13, 2026 -Gregory James at La Te Da
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April 13, 2026 -Josh Kiser at Hank’s Hair of the Dog Saloon
Fishmonster Max- Daily Party Boat Fishing
Join the Fishmonster Max daily party boat fishing adventure at A & B Marina in Key West's historic seaport. Enjoy a vibrant atmosphere with live…
$85.00
Yoga on the Beach – Ft Zachary Taylor
Join a rejuvenating session of Yoga on the Beach at Fort Zachary Taylor State Park in Key West. Emphasizing breathtaking sunset views, this experience offers…
$20
Aqua Yoga at Southernmost Beach Resort
Experience the tranquility of Aqua Yoga at Southernmost Beach Resort in Key West, a luxurious island escape offering lush gardens and ocean views. Immerse yourself…
$20
Lance Taylor at Two Friends Patio Restaurant
Lance Taylor captivates audiences at Two Friends Patio Restaurant with his exceptional musical talent. As a skilled musician, Lance enhances the vibrant atmosphere of this…
Free
Rolando Rojas at Sloppy Joe’s Bar
At Sloppy Joe's Bar, Rolando Rojas captivates audiences with his dynamic and emotive performances. Known for his innovative musical style that blends diverse cultural influences,…
Free
Distillery Tour – Key West Legal Rum Distillery
Experience the vibrant nightlife atmosphere at Key West First Legal Rum Distillery. Enjoy free daily tours and tastings in this historic seaport location, once a…
Free
Mojito Class by Key West Legal Rum Distillery – Min 4 people
Join the Mojito Class at Key West Legal Rum Distillery with a minimum of four people for an unforgettable experience. Enjoy lively entertainment as expert…
$75.00
Bradd Shadduck at Irish Kevin’s Bar
Bradd Shadduck brings vibrant energy to Irish Kevin's Bar in Old Town Key West. Known for his engaging performances, he captivates audiences with lively music…
Free
Nick Norman at Rams Head Southernmost
Experience the soulful sounds of Nick Norman at Rams Head Southernmost. This South Carolina native and Key West resident captivates with his heartfelt vocals and…
Free
Glass Bottom Boat Cruise – Key West’s Window to the Sea
Experience the Glass Bottom Boat Cruise in Key West, where a charming entertainer guides you through the vibrant marine life visible beneath your feet. With…
$69.95
Tim Hollohan at Sloppy Joe’s Bar
Tim Hollohan graces the stage at Sloppy Joe's Bar in Key West, delivering a captivating live music experience in a historic setting. Known for his…
Free
Jay Klein at Schooner Wharf Bar
At Schooner Wharf Bar, Jay Klein mesmerizes audiences with his musical talent, blending captivating performances with Key West's relaxed atmosphere. Known as an entrepreneur and…
Free
Zack Seemiller at Hog’s Breath Saloon
Experience the remarkable Zack Seemiller at Hog's Breath Saloon in Key West. An accomplished musician and performer, Zack captivates audiences with his dynamic stage presence…
Free
Webb Dillard at Rick’s Bar Downstairs Stage
Experience the vibrant energy of Webb Dillard at Rick's Bar Downstairs Stage in Key West. As the creative visionary behind TikiBar Nation, Dillard brings his…
Free
Tom Curtis Jr at Hank’s Hair of the Dog Saloon
Tom Curtis Jr brings his dynamic musical talents to Hank's Hair of the Dog Saloon in Key West. Known for his captivating performances, Tom entertains…
Free
Rick Fusco at Two Friends Patio Restaurant
Rick Fusco enchants audiences at Two Friends Patio Restaurant with his musical talents. Nestled in the heart of Key West, this lively venue offers a…
Free
Glass Bottom Boat Cruise – Key West’s Window to the Sea
Embark on the Glass Bottom Boat Cruise in Key West where the stars of the show are the vibrant marine life visible through the crystal-clear…
$69.95
Jon Hollywood at Tiki House Key West
Experience the charismatic presence of Jon Hollywood at Tiki House Key West. Known for his captivating storytelling and dynamic personality, Jon enchants audiences with his…
Free
Oren Polak at Irish Kevin’s Bar
Oren Polak captivates audiences at Irish Kevin's Bar with his versatile music and charismatic stage presence. Known for delivering Music for Everyone, Everywhere, his performances…
Free
Reef Snorkeling, Dolphin Watch Eco Tour & Sunset Cruise
Join Sunset Watersports in Key West's Historic Seaport for an unforgettable adventure. Although details about the entertainer are sparse, the experienced staff ensures a thrilling…
$79.95
Just George at Rick’s Bar Downstairs Stage
Experience the enchanting acoustic performances of Just George at Rick's Bar Downstairs Stage in Key West. This talented musician brings his soulful tunes to life,…
Free
Glass Bottom Boat Cruise – Key West’s Window to the Sea
Join us for the Glass Bottom Boat Cruise in Key West, a unique journey showcasing the magical underwater world. Delight in live entertainment that enhances…
$69.95
Cliff Cody at Mac’s Place
Experience the soulful sounds of Cliff Cody at Mac's Place, where the Texas-born, Key West-based indie country artist captivates with his powerful voice and heartfelt…
Free
Telephone Tag at Hog’s Breath Saloon
Immerse yourself in the playful antics of Telephone Tag at Hog's Breath Saloon, where missed calls and voicemails transform into a lively communication challenge. As…
Free
Glow Hours on Hugh’s View
Glow Hours on Hugh's View at The Studios of Key West promises an enchanting evening with live music at its heart. Overlooking the vibrant cityscape…
Caribe of Key West at El Meson de Pepes on Mallory Square
Experience the vibrant sounds of Caribe of Key West at El Meson de Pepes on Mallory Square. This talented entertainer infuses lively Cuban rhythms into…
Sunset Celebration at Mallory Square
Experience the vibrant Sunset Celebration at Mallory Square, where entertainers steal the show. Marvel at captivating performances by jugglers and the renowned cat man, set…
Free
Scott Morlock at Hank’s Hair of the Dog Saloon
Scott Morlock, a talented musician known for his captivating performances, takes the stage at Hank's Hair of the Dog Saloon in Key West's Old Town.…
Free
Tony Roberts at Rams Head Southernmost
Experience the charismatic Tony Roberts at Rams Head Southernmost. Known for his versatile talent in film, television, and theater, Tony captivates audiences with his distinctive…
Free
World Famous 801 Girls- 5pm Show
Experience the unparalleled charisma of the World Famous 801 Girls at their 5pm show. These dynamic drag queens captivate audiences with their dazzling performances and…
CW Colt at Two Friends Patio Restaurant
CW Colt, a talented musician, captivates audiences at Two Friends Patio Restaurant in Key West. With his engaging performances, CW Colt brings a unique energy…
Free
Pete & Larry Sloppy 2nds at Sloppy Joe’s Bar
Experience the eclectic and innovative performance of Pete & Larry Sloppy 2nds at Sloppy Joe's Bar. This dynamic duo captivates audiences with their spontaneous energy…
Free
NY Pauly at Irish Kevin’s Bar
Experience the unforgettable allure of NY Pauly at Irish Kevin's Bar. A legendary performer, he captivates audiences with his seamless blend of music and entertainment.…
Free
Barrett Thomas at The Alamo Key West
Barrett Thomas is a dynamic musician based in Key West, known for his captivating live performances at The Alamo Key West. As a talented looper,…
Free
Magic The Gathering Night at The Retro Room
Join the enchanting Magic The Gathering Night at The Retro Room in Old Town Key West. This nostalgic café offers a captivating blend of interactive…
Free
Charity Bingo at The Green Parrot
Join us at The Green Parrot in Key West for Charity Bingo, where vibrant entertainment takes center stage in this historic dive bar. Enjoy the…
Free
Joe The Show at Schooner Wharf Bar
Experience the incredible talent of Joe The Show at Schooner Wharf Bar, a dedicated musician known for his dynamic energy and tireless work ethic. Performing…
Free
Lary Smith Jazz Jam at William Weech American Legion Post 168
Join renowned musician Larry Smith for an unforgettable Jazz Jam at the William Weech American Legion Post 168 in Key West. Experience vibrant jazz rhythms…
Free
Charles Miller at Rick’s Bar Downstairs Stage
Charlie Miller, a vibrant musician and adventurous sailor, takes the stage at Rick's Bar in Key West. Known as a modern-day pirate and gypsy, Miller…
Free
Gastor Almonte at Comedy Key West
Gastor Almonte is a celebrated Dominican-American comedian renowned for his engaging storytelling and sharp wit. Based in New York City, he captivates audiences with personal…
$35
Jefff Clark at Tiki House Key West
Jefff Clark, a rising music artist, captivates audiences at Tiki House Key West with his innovative soundscapes and engaging performances. Known for his passion for…
Free
Elle Haley at Halo Rooftop Lounge Bar at The Saint
Elle Haley captivates audiences with her vibrant performances at the Halo Rooftop Lounge Bar located in The Saint Hotel, Key West. Known for her soulful…
Free
Gregory James at La Te Da
Gregory James is a versatile performer showcasing his talents at La Te Da, Key West. Known for his skills in music theatre, tap, ballet, and…
Free
Josh Kiser at Hank’s Hair of the Dog Saloon
Experience the soulful melodies of Josh Kiser at Hank's Hair of the Dog Saloon. This Cleveland, Tennessee-born singer-songwriter captivates audiences with his blend of '90s…
Free
Tuesday, April 14, 2026
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April 14, 2026 -Ambitious Morning Runners
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April 14, 2026 -Fishmonster Max- Daily Party Boat Fishing
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April 14, 2026 -Rising Star Series: Using AI to Improve Business Efficiency and Effectiveness
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April 14, 2026 -Yoga on the Beach – Ft Zachary Taylor
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April 14, 2026 -Jonthan Williams at Two Friends Patio Restaurant
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April 14, 2026 -Prime of Life Yoga with Monica Haskell
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April 14, 2026 -Sid the Bayou Kid at Sloppy Joe’s Bar
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April 14, 2026 -Distillery Tour – Key West Legal Rum Distillery
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April 14, 2026 -Mojito Class by Key West Legal Rum Distillery – Min 4 people
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April 14, 2026 -Bradd Shadduck at Irish Kevin’s Bar
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April 14, 2026 -Ross Brown at Rams Head Southernmost
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April 14, 2026 -Glass Bottom Boat Cruise – Key West’s Window to the Sea
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April 14, 2026 -Caleb Tyler at Tiki House Key West
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April 14, 2026 -Eric Aardema at Hog’s Breath Saloon
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April 14, 2026 -Jefff Clark at Sloppy Joe’s Bar
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April 14, 2026 -Shanty Hounds at Rick’s Bar Downstairs Stage
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April 14, 2026 -Oren Polak at Schooner Wharf Bar
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April 14, 2026 -Tony Baltimore at Hank’s Hair of the Dog Saloon
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April 14, 2026 -CW Colt at Two Friends Patio Restaurant
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April 14, 2026 -Glass Bottom Boat Cruise – Key West’s Window to the Sea
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April 14, 2026 -Industry Night at The Retro Room
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April 14, 2026 -Irish Kevin at Irish Kevin’s Bar
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April 14, 2026 -Joe The Show at Tiki House Key West
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April 14, 2026 -Reef Snorkeling, Dolphin Watch Eco Tour & Sunset Cruise
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April 14, 2026 -Jesse Lee at Rick’s Bar Downstairs Stage
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April 14, 2026 -Glass Bottom Boat Cruise – Key West’s Window to the Sea
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April 14, 2026 -Cliff Cody at Mac’s Place
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April 14, 2026 -Telephone Tag at Hog’s Breath Saloon
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April 14, 2026 -Glow Hours on Hugh’s View
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April 14, 2026 -Caribe of Key West at El Meson de Pepes on Mallory Square
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April 14, 2026 -Sunset Celebration at Mallory Square
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April 14, 2026 -World Famous 801 Girls- 5pm Show
-
April 14, 2026 -Jay Klein at Hank’s Hair of the Dog Saloon
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April 14, 2026 -Zack Seemiller at Rams Head Southernmost
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April 14, 2026 -Ericson Holt at Two Friends Patio Restaurant
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April 14, 2026 -Jerico Duo at Sloppy Joe’s Bar
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April 14, 2026 -Tom Petty Night at Green Parrot Bar
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April 14, 2026 -Bo Fodor at RockHouse Live Key West
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April 14, 2026 -Happy Dog at The Alamo Key West
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April 14, 2026 -NY Pauly at Irish Kevin’s Bar
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April 14, 2026 -Gary Hempsey at Schooner Wharf Bar
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April 14, 2026 -Joe the Show at Rick’s Bar Downstairs Stage
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April 14, 2026 -Aaron Hudgins at Tiki House Key West
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April 14, 2026 -Gastor Almonte at Comedy Key West
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April 14, 2026 -Marshall Morlock at Halo Rooftop Lounge Bar at The Saint
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April 14, 2026 -Ronnie & Gregory at La Te Da
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April 14, 2026 -Elle Haley at Hank’s Hair of the Dog Saloon
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April 14, 2026 -Randy Roberts at La Te Da
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April 14, 2026 -Tom Petty Night at Green Parrot Bar
Ambitious Morning Runners
Ambitious Morning Runners gather at the serene White Street Pier in Key West, a perfect backdrop for this invigorating event. While the pier offers breathtaking…
Free
Fishmonster Max- Daily Party Boat Fishing
Join Fishmonster Max for a daily party boat fishing experience at A & B Marina in Key West's historic seaport. Enjoy live entertainment amidst the…
$85.00
Rising Star Series: Using AI to Improve Business Efficiency and Effectiveness
Join the Rising Star Series, hosted by the Greater Key West Chamber of Commerce at the elegant Casa Marina Resort. This interactive seminar focuses on…
Free
Yoga on the Beach – Ft Zachary Taylor
Experience tranquility with Yoga on the Beach at Fort Zachary Taylor State Park in Key West. Immerse yourself in a unique session led by a…
$20
Jonthan Williams at Two Friends Patio Restaurant
Jonathan Williams captivates audiences at Two Friends Patio Restaurant with his dynamic live performances. Set against the backdrop of Key West's vibrant Duval Street, he…
Free
Prime of Life Yoga with Monica Haskell
Join Monica Haskell for Prime of Life Yoga, a rejuvenating experience held at the unique Key West Tropical Forest & Botanical Garden. Monica, renowned for…
$20
Sid the Bayou Kid at Sloppy Joe’s Bar
Sid the Bayou Kid, a vibrant young musician from Louisiana, captivates audiences at Sloppy Joe's Bar with his bluesy harmonica tunes and storytelling flair. Embracing…
Free
Distillery Tour – Key West Legal Rum Distillery
Experience the vibrant Key West Legal Rum Distillery with daily free tours and tastings. Although there’s no specific entertainer mentioned, the lively setting itself offers…
Free
Mojito Class by Key West Legal Rum Distillery – Min 4 people
Join the Mojito Class at Key West Legal Rum Distillery with a minimum group of four. The entertainer, a spirited mixologist, will guide you through…
$75.00
Bradd Shadduck at Irish Kevin’s Bar
Bradd Shadduck captivates audiences at Irish Kevin's Bar with his dynamic performances and engaging presence. Bringing a lively mix of music to the heart of…
Free
Ross Brown at Rams Head Southernmost
Ross Brown, a versatile musician from Key West, captivates audiences at Rams Head Southernmost with his unique blend of creativity and adventure. Known as a…
Free
Glass Bottom Boat Cruise – Key West’s Window to the Sea
Join the Glass Bottom Boat Cruise for a unique maritime experience in Key West. While the tour offers breathtaking views of vibrant marine life through…
$69.95
Caleb Tyler at Tiki House Key West
Caleb Tyler brings his dynamic musical talent to Tiki House Key West, enlivening the cozy tiki bar with captivating performances. Known for his engaging presence,…
Free
Eric Aardema at Hog’s Breath Saloon
Eric Aardema graces the stage at Hog's Breath Saloon, captivating audiences with his dynamic performances and magnetic presence. In Key West's vibrant Mallory Square District,…
Free
Jefff Clark at Sloppy Joe’s Bar
Jefff Clark is an emerging music artist captivating audiences at Sloppy Joe's Bar, a historic Key West venue. Known for his creativity and innovative sound,…
Free
Shanty Hounds at Rick’s Bar Downstairs Stage
Experience the vibrant acoustic duo Shanty Hounds at Rick's Bar Downstairs Stage in Key West. Dani Hoy and Key West Chris Rehm bring an inventive…
Free
Oren Polak at Schooner Wharf Bar
Oren Polak graces the stage at Schooner Wharf Bar with his dynamic performances and unique sound, embodying his mission of Music for Everyone, Everywhere. As…
Free
Tony Baltimore at Hank’s Hair of the Dog Saloon
Tony Baltimore, a versatile singer/songwriter, enchants audiences with his genre-bending alternative roots-rock at Hank's Hair of the Dog Saloon. Raised by Italian immigrant parents in…
Free
CW Colt at Two Friends Patio Restaurant
Experience the captivating performance of CW Colt at Two Friends Patio Restaurant. Known for his engaging stage presence and exceptional musical talent, CW Colt delights…
Free
Glass Bottom Boat Cruise – Key West’s Window to the Sea
Experience the vibrant marine life of Key West aboard the Glass Bottom Boat Cruise, featuring captivating performances by talented local entertainers. This unique excursion combines…
$69.95
Industry Night at The Retro Room
Enjoy a night at The Retro Room in Old Town Key West where entertainment takes center stage. This nostalgic café and restaurant offers a unique…
Free
Irish Kevin at Irish Kevin’s Bar
Irish Kevin, a charismatic and humor-filled entertainer, brings his laid-back charm to Irish Kevin's Bar in Key West. Known for captivating audiences with his singing…
Free
Joe The Show at Tiki House Key West
Catch Joe The Show at Tiki House Key West, where his dynamic energy and exceptional talent captivate audiences nightly. Known for his tireless work ethic…
Free
Reef Snorkeling, Dolphin Watch Eco Tour & Sunset Cruise
Experience the vibrant Reef Snorkeling, Dolphin Watch Eco Tour & Sunset Cruise at Sunset Watersports in Key West's Historic Seaport. Dive into an adventure with…
$79.95
Jesse Lee at Rick’s Bar Downstairs Stage
Catch the vibrant sounds of emerging musician Jesse Lee Jr. at Rick's Bar Downstairs Stage in Key West. Originally from New Jersey, Jesse relocated to…
Free
Glass Bottom Boat Cruise – Key West’s Window to the Sea
Embark on the Glass Bottom Boat Cruise in Key West, where the ocean comes alive beneath your feet. Marvel at the vibrant marine life through…
$69.95
Cliff Cody at Mac’s Place
Enjoy an unforgettable evening with Cliff Cody at Mac's Place, a vibrant waterfront bar in Key West. The Texas-born, Key West-based indie country singer captivates…
Free
Telephone Tag at Hog’s Breath Saloon
Experience the playful antics of Telephone Tag at Hog's Breath Saloon in Key West. This unique entertainer brings humor to the art of communication, engaging…
Free
Glow Hours on Hugh’s View
Experience an enchanting evening at Glow Hours on Hugh's View, featuring captivating performances by world-class artists at The Studios of Key West. Set in a…
Caribe of Key West at El Meson de Pepes on Mallory Square
Experience the vibrant energy of Caribe of Key West at El Meson de Pepe's on Mallory Square. This talented entertainer captivates audiences with lively performances,…
Sunset Celebration at Mallory Square
Experience the Sunset Celebration at Mallory Square, a vibrant Key West spectacle where dazzling sunsets meet enthralling entertainment. The famous cat man steals the show…
Free
World Famous 801 Girls- 5pm Show
Experience the dynamic performances of the World Famous 801 Girls at their 5pm show. These talented drag queens captivate audiences with their charisma, artistry, and…
Jay Klein at Hank’s Hair of the Dog Saloon
Jay Klein, a multifaceted entrepreneur and musician, captivates audiences at Hank's Hair of the Dog Saloon in Key West's Old Town. Known for his innovation…
Free
Zack Seemiller at Rams Head Southernmost
Zack Seemiller, a dynamic musician and performer, captivates audiences with his engaging live shows at Rams Head Southernmost. Known for his motivational prowess, Zack transforms…
Free
Ericson Holt at Two Friends Patio Restaurant
Experience the soulful tunes of Ericson Holt at Two Friends Patio Restaurant. Known for his captivating performances, Holt brings a dynamic blend of blues and…
Free
Jerico Duo at Sloppy Joe’s Bar
Experience the electrifying performance of the Jerico Rockabilly Duo at Sloppy Joe's Bar, an iconic Key West venue. Known for their dynamic rock 'n' roll…
Free
Tom Petty Night at Green Parrot Bar
Tom Petty Night at Green Parrot Bar promises an electrifying tribute to the legendary rocker. Set in Key West's iconic, lively dive bar, the event…
Free
Bo Fodor at RockHouse Live Key West
Bo Fodor brings his innovative artistry and captivating storytelling to RockHouse Live Key West. Known for blending traditional techniques with contemporary ideas, Bo inspires audiences…
Free
Happy Dog at The Alamo Key West
Experience the electrifying performance of Happy Dog Band, an improvisational jam band channeling the essence of the psychedelic era, at The Alamo Key West. Known…
Free
NY Pauly at Irish Kevin’s Bar
NY Pauly is a legendary performer at Irish Kevin’s Bar in Key West. Renowned for his captivating shows, he seamlessly blends music and entertainment, creating…
Free
Gary Hempsey at Schooner Wharf Bar
Experience the captivating sounds of musician Gary Hempsey at the vibrant Schooner Wharf Bar in Key West. Known for his engaging performances, Gary brings the…
Free
Joe the Show at Rick’s Bar Downstairs Stage
Experience the remarkable talents of Joe The Show at Rick's Bar Downstairs Stage. Known for his dynamic energy and tireless dedication, Joe The Show captivates…
Free
Aaron Hudgins at Tiki House Key West
Experience the captivating sounds of musician Aaron Hudgins at Tiki House Key West. Known for his engaging performances, Aaron brings an energetic and soulful vibe…
Free
Gastor Almonte at Comedy Key West
Gastor Almonte, a Dominican-American comedian based in New York City, captivates audiences with his engaging storytelling and warm delivery. Known for blending personal anecdotes with…
$35
Marshall Morlock at Halo Rooftop Lounge Bar at The Saint
Marshall Morlock, the charismatic frontman of The Marshall Morlock Band, is set to captivate audiences at Halo Rooftop Lounge Bar at The Saint. Known for…
Free
Ronnie & Gregory at La Te Da
Ronnie and Gregory light up La Te Da in Key West with their engaging and dynamic performances. Renowned for their vibrant personalities and synergy, the…
Free
Elle Haley at Hank’s Hair of the Dog Saloon
Elle Haley, a vibrant musician from the Florida Keys, captivates audiences with soulful performances at Hank's Hair of the Dog Saloon. Known for her engaging…
Free
Randy Roberts at La Te Da
Randy Roberts at La Te Da is an unparalleled spectacle in Key West's cabaret scene. Renowned for his awe-inspiring live vocals and captivating impersonations of…
$35
Tom Petty Night at Green Parrot Bar
Celebrate Tom Petty Night at the Green Parrot Bar in Key West, a vibrant dive bar bursting with charm and history. Enjoy classic hits and…
Free
Wednesday, April 15, 2026
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April 15, 2026 -Fishmonster Max- Daily Party Boat Fishing
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April 15, 2026 -Yoga on the Beach – Ft Zachary Taylor
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April 15, 2026 -Aqua Yoga at Southernmost Beach Resort
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April 15, 2026 -Alfonse at Two Friends Patio Restaurant
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April 15, 2026 -Zack Seemiller at Sloppy Joe’s Bar
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April 15, 2026 -Mojito Class by Key West Legal Rum Distillery – Min 4 people
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April 15, 2026 -Distillery Tour – Key West Legal Rum Distillery
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April 15, 2026 -Barrett Thomas at Rams Head Southernmost
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April 15, 2026 -Oren Polak at Irish Kevin’s Bar
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April 15, 2026 -Glass Bottom Boat Cruise – Key West’s Window to the Sea
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April 15, 2026 -Andy Mauerman at Hog’s Breath Saloon
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April 15, 2026 -Andy Westcott at Sloppy Joe’s Bar
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April 15, 2026 -Michael Corleto at Rick’s Bar Downstairs Stage
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April 15, 2026 -Tony Baltimore at Schooner Wharf Bar
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April 15, 2026 -Victoria Leigh at Tiki House Key West
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April 15, 2026 -Glass Bottom Boat Cruise – Key West’s Window to the Sea
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April 15, 2026 -Bradd Shadduck at Irish Kevin’s Bar
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April 15, 2026 -Reef Snorkeling, Dolphin Watch Eco Tour & Sunset Cruise
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April 15, 2026 -Harley Ray at Rick’s Bar Downstairs Stage
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April 15, 2026 -Jonthan Williams at Two Friends Patio Restaurant
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April 15, 2026 -Glass Bottom Boat Cruise – Key West’s Window to the Sea
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April 15, 2026 -Nick Norman at Mac’s Place
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April 15, 2026 -Sewing: New Sewing Era with Suely Moura
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April 15, 2026 -Telephone Tag at Hog’s Breath Saloon
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April 15, 2026 -Sunset Celebration at Mallory Square
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April 15, 2026 -Caribe of Key West at El Meson de Pepes on Mallory Square
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April 15, 2026 -World Famous 801 Girls- 5pm Show
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April 15, 2026 -Jay Bangles at Tiki House Key West
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April 15, 2026 -John Sausser at Rams Head Southernmost
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April 15, 2026 -Mojito at Sloppy Joe’s Bar
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April 15, 2026 -Happy Dog at The Alamo Key West
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April 15, 2026 -Irish Kevin at Irish Kevin’s Bar
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April 15, 2026 -Live music series
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April 15, 2026 -Live music series
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April 15, 2026 -Line Dancing at Kaya Island Eats
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April 15, 2026 -Ericson Holt at Two Friends Patio Restaurant
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April 15, 2026 -Andrew B. at Rick’s Bar Downstairs Stage
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April 15, 2026 -Arts & Drafts at The Retro Room
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April 15, 2026 -Jefff Clark at Schooner Wharf Bar
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April 15, 2026 -Magic Of Frank Everhart at Schooner Wharf Bar
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April 15, 2026 -Jay Bangles at Tiki House Key West
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April 15, 2026 -Ronnie & Gregory at La Te Da
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April 15, 2026 -Uke Night w/ Special Guest Jefff Clark! at Green Parrot Bar
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April 15, 2026 -Zach Lovering at Halo Rooftop Lounge Bar at The Saint
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April 15, 2026 -Amos Gill at Comedy Key West
Fishmonster Max- Daily Party Boat Fishing
Join the Fishmonster Max daily party boat fishing excursion at A & B Marina in Key West's historic seaport. While the details of the entertainer…
$85.00
Yoga on the Beach – Ft Zachary Taylor
Join an invigorating Yoga on the Beach session at Fort Zachary Taylor State Park in Key West. Led by renowned instructors, this experience combines the…
$20
Aqua Yoga at Southernmost Beach Resort
Experience the serene Aqua Yoga session at Southernmost Beach Resort, led by an exceptional instructor who brings a harmonious blend of relaxation and fitness to…
$20
Alfonse at Two Friends Patio Restaurant
Alfonse brings vibrant energy to Two Friends Patio Restaurant with his captivating live performances. As a talented musician, he enhances the island dining experience with…
Free
Zack Seemiller at Sloppy Joe’s Bar
At Sloppy Joe's Bar, Zack Seemiller captivates audiences with his dynamic musical performances. Known for his motivational speaking and songwriting talent, Zack infuses his shows…
Free
Mojito Class by Key West Legal Rum Distillery – Min 4 people
Join the Mojito Class at Key West First Legal Rum Distillery, where a charismatic entertainer will guide you through a lively mojito-making experience. Delight in…
$75.00
Distillery Tour – Key West Legal Rum Distillery
Explore the Key West First Legal Rum Distillery, nestled in the Historic Seaport. Delight in daily tours and rum samples while embracing vibrant nightlife vibes.…
Free
Barrett Thomas at Rams Head Southernmost
Barrett Thomas is a dynamic live musician and talented looper from Key West, known for his innovative performances. With skillful sound layering, Barrett creates captivating…
Free
Oren Polak at Irish Kevin’s Bar
Oren Polak captivates audiences at Irish Kevin's Bar with his versatile music and charismatic stage presence. Known for delivering Music for Everyone, Everywhere, his performances…
Free
Glass Bottom Boat Cruise – Key West’s Window to the Sea
Join the Glass Bottom Boat Cruise in Key West for an unforgettable journey beneath the sea. While soaking in vibrant marine life through crystal-clear waters,…
$69.95
Andy Mauerman at Hog’s Breath Saloon
Andy Mauerman, a musician dedicated to experiential living, brings his passion for meaningful connections to Hog's Breath Saloon. Emphasizing personal growth through music, Andy's performances…
Free
Andy Westcott at Sloppy Joe’s Bar
Andy Westcott, a talented musician from Key West, enchants audiences at Sloppy Joe's Bar with his unique sound and captivating performances. Gaining a loyal following,…
Free
Michael Corleto at Rick’s Bar Downstairs Stage
Michael Corleto, a gifted singer-songwriter and multi-instrumentalist from Maine, captivates audiences with his heartfelt lyrics and rich melodies at Rick's Bar Downstairs Stage. His dynamic…
Free
Tony Baltimore at Schooner Wharf Bar
Tony Baltimore is a dynamic singer-songwriter known for his genre-bending alternative roots-rock sound. Born to Italian immigrant parents in Maryland, he brings a strong work…
Free
Victoria Leigh at Tiki House Key West
Experience the dynamic performances of Victoria Leigh at the Tiki House Key West. This talented Florida Keys musician captivates audiences with her feel-good covers, innovative…
Free
Glass Bottom Boat Cruise – Key West’s Window to the Sea
The Glass Bottom Boat Cruise in Key West offers a unique marine adventure, enhanced by a captivating entertainer who brings the vibrant sea life into…
$69.95
Bradd Shadduck at Irish Kevin’s Bar
Experience lively entertainment at Irish Kevin's Bar as Bradd Shadduck takes the stage. Known for his engaging performances, Bradd captivates audiences with his musical talent…
Free
Reef Snorkeling, Dolphin Watch Eco Tour & Sunset Cruise
Experience an unforgettable adventure with Sunset Watersports' Reef Snorkeling, Dolphin Watch Eco Tour, and Sunset Cruise in Key West. Guided by knowledgeable and engaging staff,…
$79.95
Harley Ray at Rick’s Bar Downstairs Stage
Experience the captivating performance of Harley Ray at Rick's Bar Downstairs Stage. An innovative songwriter, Ray delivers genuine melodies and lyrics that resonate deeply with…
Free
Jonthan Williams at Two Friends Patio Restaurant
Jonathan Williams brings vibrant energy and exceptional musical talent to Two Friends Patio Restaurant. As a celebrated musician, his performances enhance the lively ambiance of…
Free
Glass Bottom Boat Cruise – Key West’s Window to the Sea
Embark on the Glass Bottom Boat Cruise in Key West for an unforgettable maritime adventure. While the vibrant marine life and crystal-clear waters captivate, it's…
$69.95
Nick Norman at Mac’s Place
Experience the soulful vocals and sharp songwriting of Nick Norman at Mac's Place. Hailing from South Carolina and based in Key West, Nick blends humor…
Free
Sewing: New Sewing Era with Suely Moura
Join the New Sewing Era with acclaimed designer and instructor Suely Moura. Over four weeks, Suely will guide you in revitalizing old clothes and crafting…
Free
Telephone Tag at Hog’s Breath Saloon
Experience the entertaining antics of Telephone Tag at Hog's Breath Saloon. This innovative act brings humor to the stage with a playful communication challenge, capturing…
Free
Sunset Celebration at Mallory Square
At Mallory Square's Sunset Celebration, experience captivating performances by diverse entertainers, including the renowned cat man, who mesmerizes audiences with his feline acrobatics. This vibrant…
Free
Caribe of Key West at El Meson de Pepes on Mallory Square
Experience the vibrant performance of Caribe of Key West at El Meson de Pepes on Mallory Square. This lively Cuban restaurant offers captivating live music,…
World Famous 801 Girls- 5pm Show
Experience the captivating talent of the World Famous 801 Girls during their 5 pm show at 801 Bourbon Bar in Key West. Renowned for their…
Jay Bangles at Tiki House Key West
Experience the vibrant energy of Jay Bangles at Tiki House Key West, where his captivating performances elevate the lively atmosphere. As co-owner and talented musician,…
Free
John Sausser at Rams Head Southernmost
John Sausser captivates audiences at Rams Head Southernmost with his dynamic performances. As a standout entertainer, he delivers an unforgettable live music experience, drawing in…
Free
Mojito at Sloppy Joe’s Bar
Experience the electrifying Mojito band at Sloppy Joe's Bar, a historic Key West icon since 1933. Nestled in the heart of Old Town, this vibrant…
Free
Happy Dog at The Alamo Key West
Experience the energetic Happy Dog Band at The Alamo Key West. This improvisational jam band captures the essence of the psychedelic era, delivering dynamic live…
Free
Irish Kevin at Irish Kevin’s Bar
Irish Kevin brings his charm and humor to Irish Kevin's Bar in Key West, captivating audiences with his laid-back, fun-loving style. Known for his genuine…
Free
Live music series
Join Beth Hataway and Johnny Veres of Electric Blue Yonder for an enchanting live music series aboard the Schooner Hindu. This talented duo, now Key…
Free
Live music series
Join Beth Hataway and Johnny Veres of Electric Blue Yonder for an enchanting night of live music with the Live Music Series at Schooner Hindu.…
Free
Line Dancing at Kaya Island Eats
Enjoy an evening of line dancing at Kaya Island Eats, where the talented entertainer sets the mood with energetic tunes. Nestled in Key West, this…
Free
Ericson Holt at Two Friends Patio Restaurant
Experience the soulful performance of musician Ericson Holt at Two Friends Patio Restaurant. Renowned for his captivating style, Holt brings his dynamic musical talent to…
Free
Andrew B. at Rick’s Bar Downstairs Stage
Experience the charismatic Andrew Burleson at Rick's Bar Downstairs Stage. Known for his engaging melodies and witty dad jokes, Andrew captivates the audience with his…
Free
Arts & Drafts at The Retro Room
Arts & Drafts at The Retro Room offers an unforgettable evening in Old Town Key West. Enjoy the lively atmosphere and a creative showcase presented…
Free
Jefff Clark at Schooner Wharf Bar
Experience the captivating performance of Jefff Clark at Schooner Wharf Bar, a rising talent in the music industry known for his innovative soundscapes and engaging…
Free
Magic Of Frank Everhart at Schooner Wharf Bar
Experience the mesmerizing Magic of Frank Everhart at Schooner Wharf Bar, where the legendary magician enchants audiences with his innovative illusions and captivating storytelling. Everhart's…
Free
Jay Bangles at Tiki House Key West
Visit Tiki House Key West for an unforgettable night with co-owner and musician Jay Bangles. Renowned for his vibrant performances, Jay's unique charm and musical…
Free
Ronnie & Gregory at La Te Da
Experience the captivating performances of Ronnie and Gregory at La Te Da, Key West's iconic cabaret venue. Known for their dynamic chemistry and vibrant personalities,…
Free
Uke Night w/ Special Guest Jefff Clark! at Green Parrot Bar
Join us at the Green Parrot Bar for Uke Night featuring special guest Jefff Clark. Immerse yourself in an unforgettable evening as Jefff Clark brings…
Free
Zach Lovering at Halo Rooftop Lounge Bar at The Saint
Zach Lovering, a vibrant local musician from the Florida Keys, captivates audiences at Halo Rooftop Lounge Bar in The Saint Hotel. His soulful melodies and…
Free
Amos Gill at Comedy Key West
Join us at Comedy Key West for an unforgettable night with Amos Gill, one of Australia's top comedians. Renowned for his sharp wit and engaging…
$35
Thursday, April 16, 2026
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April 16, 2026 -Ambitious Morning Runners
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April 16, 2026 -Fishmonster Max- Daily Party Boat Fishing
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April 16, 2026 -Yoga on the Beach – Ft Zachary Taylor
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April 16, 2026 -Alfonse at Two Friends Patio Restaurant
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April 16, 2026 -Prime of Life Yoga with Monica Haskell
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April 16, 2026 -Justin Angelo at Sloppy Joe’s Bar
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April 16, 2026 -Distillery Tour – Key West Legal Rum Distillery
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April 16, 2026 -Mojito Class by Key West Legal Rum Distillery – Min 4 people
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April 16, 2026 -Mylo O’Maolain at Irish Kevin’s Bar
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April 16, 2026 -Robert Douglas at Rams Head Southernmost
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April 16, 2026 -Trenton Chandler at Rick’s DownStairs Stage
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April 16, 2026 -Glass Bottom Boat Cruise – Key West’s Window to the Sea
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April 16, 2026 -Dan Harvey at Hog’s Breath Saloon
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April 16, 2026 -Ross Brown at Schooner Wharf Bar
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April 16, 2026 -Tim Hollohan at Sloppy Joe’s Bar
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April 16, 2026 -A Pirate Looks Back: Jimmy Buffett Tribute Show at Comedy Key West
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April 16, 2026 -Truman Waterfront Farmers Market
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April 16, 2026 -Shanty Hounds at Two Friends Patio Restaurant
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April 16, 2026 -Glass Bottom Boat Cruise – Key West’s Window to the Sea
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April 16, 2026 -Jefff Clark at Tiki House Key West
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April 16, 2026 -Just George at The Alamo Key West
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April 16, 2026 -Irish Kevin at Irish Kevin’s Bar
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April 16, 2026 -Reef Snorkeling, Dolphin Watch Eco Tour & Sunset Cruise
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April 16, 2026 -Jeff Harris at Rick’s Bar Downstairs
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April 16, 2026 -Glass Bottom Boat Cruise – Key West’s Window to the Sea
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April 16, 2026 -Collette Campbell at Mac’s Place
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April 16, 2026 -Telephone Tag at Hog’s Breath Saloon
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April 16, 2026 -World Famous 801 Girls- 5pm Show
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April 16, 2026 -Elle Haley at Hank’s Hair of the Dog Saloon
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April 16, 2026 -Micah Read at Rams Head Southernmost
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April 16, 2026 -Ice Society Ice Bath Thursdays
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April 16, 2026 -Caribe of Key West at El Meson de Pepes on Mallory Square
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April 16, 2026 -Sunset Celebration at Mallory Square
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April 16, 2026 -Ericson Holt at Two Friends Patio Restaurant
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April 16, 2026 -AstroYeti at Green Parrot Bar
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April 16, 2026 -Preacher Pete Presents at Sloppy Joe’s Bar
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April 16, 2026 -Bria Ansara at Berlin’s Cocktail Bar
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April 16, 2026 -Filming Sit with Kit Podcast Episodes
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April 16, 2026 -Barrett Thomas at The Alamo Key West
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April 16, 2026 -Dinner with the Dead – Rainbow Full of Sound Waynard in the Grand Piano at Viva Argentinian Steakhouse
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April 16, 2026 -April’s Walk On White
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April 16, 2026 -Terri, Larry and Friends Live Music at William Weech American Legion Post 168
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April 16, 2026 -Oren Polak at Irish Kevin’s Bar
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April 16, 2026 -Andy’s Cabana Open Mic No Mic Night
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April 16, 2026 -Catch The Mania Trivia at Brady’s Pub
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April 16, 2026 -Joe The Show at Rick’s Bar Downstairs Stage
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April 16, 2026 -Magic Of Frank Everhart at Schooner Wharf Bar
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April 16, 2026 -Wicked Bingo at The Retro Room
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April 16, 2026 -Nick Brownell at Schooner Wharf Bar
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April 16, 2026 -Zach Lovering at Halo Rooftop Lounge Bar at The Saint
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April 16, 2026 -Kristen McNamara at La Te Da
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April 16, 2026 -Tony Baltimore at Tiki House Key West
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April 16, 2026 -Amos Gill at Comedy Key West
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April 16, 2026 -AstroYeti at Green Parrot Bar
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April 16, 2026 -Randy Roberts at La Te Da
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April 16, 2026 -AstroYeti at Green Parrot Bar
Ambitious Morning Runners
The Ambitious Morning Runners event at White Street Pier in Key West features live entertainment against a stunning oceanfront backdrop. As runners gather to experience…
Free
Fishmonster Max- Daily Party Boat Fishing
Join the Fishmonster Max for a memorable daily party boat fishing adventure departing from A & B Marina in Key West's historic seaport. Experience lively…
$85.00
Yoga on the Beach – Ft Zachary Taylor
Experience tranquility at Yoga on the Beach with renowned instructor in the serene setting of Fort Zachary Taylor State Park, Key West. Enjoy a unique…
$20
Alfonse at Two Friends Patio Restaurant
Alfonse captivates audiences with his dynamic performances at Two Friends Patio Restaurant. Known for creating an enchanting atmosphere, he enhances the island dining experience with…
Free
Prime of Life Yoga with Monica Haskell
Join Monica Haskell for Prime of Life Yoga at the Key West Tropical Forest & Botanical Garden. Monica brings her expertise to this serene setting,…
$20
Justin Angelo at Sloppy Joe’s Bar
Experience the captivating performances of Justin Angelo at Sloppy Joe's Bar, an iconic Key West venue. A versatile musician and songcrafter, Justin draws inspiration from…
Free
Distillery Tour – Key West Legal Rum Distillery
Experience the vibrant nightlife atmosphere at Key West First Legal Rum Distillery in the Historic Seaport. Enjoy daily free tours, rum samples, and mojito-making classes.…
Free
Mojito Class by Key West Legal Rum Distillery – Min 4 people
Join the Mojito Class at Key West Legal Rum Distillery, where a charismatic entertainer guides you through the art of crafting the perfect mojito. Set…
$75.00
Mylo O’Maolain at Irish Kevin’s Bar
Mylo O’Maolain captivates crowds at Irish Kevin’s Bar with his dynamic performances and engaging stage presence. Known for his unique blend of traditional and contemporary…
Free
Robert Douglas at Rams Head Southernmost
Experience the captivating performance of Robert Douglas at Rams Head Southernmost. Known for his soulful melodies and dynamic stage presence, Robert enchants audiences in this…
Free
Trenton Chandler at Rick’s DownStairs Stage
Trenton Chandler, a talented country musician hailing from Shallowater, Texas, brings his heartfelt compositions to Rick's DownStairs Stage. Inspired by West Texas legends like Buddy…
Free
Glass Bottom Boat Cruise – Key West’s Window to the Sea
Explore the vibrant marine life of the Florida Keys on the Glass Bottom Boat Cruise, departing from Fury Key West. This captivating experience promises unforgettable…
$69.95
Dan Harvey at Hog’s Breath Saloon
Dan Harvey captivates audiences at Hog's Breath Saloon in Key West with his versatile musical talents. Known for his unique live music and DJ hybrid…
Free
Ross Brown at Schooner Wharf Bar
Ross Brown is a talented musician based in Key West, Florida, known for his dynamic performances at Schooner Wharf Bar. Embracing a lifestyle infused with…
Free
Tim Hollohan at Sloppy Joe’s Bar
Tim Hollohan brings his musical talent to the iconic Sloppy Joe's Bar in Key West. Known for electrifying performances, Tim captivates audiences with his dynamic…
Free
A Pirate Looks Back: Jimmy Buffett Tribute Show at Comedy Key West
At A Pirate Looks Back: Jimmy Buffett Tribute Show, acclaimed performer Caleb Hogan captures the essence of legendary musician Jimmy Buffett. With his vibrant portrayal…
$28
Truman Waterfront Farmers Market
At Truman Waterfront Farmers Market in Key West, enjoy lively performances at the amphitheater amidst a vibrant community setting. While vibrant stalls offer local produce…
Free
Shanty Hounds at Two Friends Patio Restaurant
Shanty Hounds, the dynamic acoustic duo of Dani Hoy and Key West Chris Rehm, brings infectious joy to Two Friends Patio Restaurant. Known for their…
Free
Glass Bottom Boat Cruise – Key West’s Window to the Sea
Experience the mesmerizing Glass Bottom Boat Cruise in Key West, featuring a captivating entertainer who brings the marine wonders to life. Depart from Fury Key…
$69.95
Jefff Clark at Tiki House Key West
Experience the captivating sounds of Jefff Clark at Tiki House Key West. A budding music artist, Jefff showcases his evolving talent with engaging visuals and…
Free
Just George at The Alamo Key West
Experience the soulful tunes of Just George at The Alamo in Key West, where he brings his heartfelt acoustic performances to life. This passionate local…
Free
Irish Kevin at Irish Kevin’s Bar
Irish Kevin, a charismatic and humorous entertainer, captivates audiences at Irish Kevin's Bar in Key West. Known for his laid-back charm and engaging performances, he…
Free
Reef Snorkeling, Dolphin Watch Eco Tour & Sunset Cruise
Experience the ultimate aquatic adventure with Reef Snorkeling, Dolphin Watch Eco Tour & Sunset Cruise at Sunset Watersports, Key West. Guided by skilled entertainers, explore…
$79.95
Jeff Harris at Rick’s Bar Downstairs
Enjoy an unforgettable evening with Jeff Harris at Rick's Bar Downstairs in Key West. A singer, songwriter, comedian, and author, Jeff captivates audiences with his…
Free
Glass Bottom Boat Cruise – Key West’s Window to the Sea
Embark on the Glass Bottom Boat Cruise from Key West with a stellar entertainer elevating the journey. Enjoy captivating commentary and lively performances as you…
$69.95
Collette Campbell at Mac’s Place
Collette Campbell, a gifted singer-songwriter from Long Island, brings her NYC musical theatre flair to Key West's Mac's Place. Leading her band, CC and The…
Free
Telephone Tag at Hog’s Breath Saloon
Experience the lively tunes of Telephone Tag at Hog's Breath Saloon. Known for their unique twist on playful communication, the entertainer brings a fun, engaging…
Free
World Famous 801 Girls- 5pm Show
Experience the captivating World Famous 801 Girls at their 5pm show, where talented drag queens dazzle the stage with charisma and flair. Held at 801…
Elle Haley at Hank’s Hair of the Dog Saloon
Elle Haley, a dynamic musician from the Florida Keys, captivates audiences with her soulful performances at Hank's Hair of the Dog Saloon. Known for her…
Free
Micah Read at Rams Head Southernmost
Micah Read captivates audiences at Rams Head Southernmost with his soulful and dynamic performances, blending a variety of musical styles. His engaging stage presence and…
Free
Ice Society Ice Bath Thursdays
Join Ice Society Ice Bath Thursdays at Kava Culture, Key West, for an invigorating experience. Alongside ice baths and conscious conversations, enjoy the vibrant atmosphere…
Free
Caribe of Key West at El Meson de Pepes on Mallory Square
Experience the vibrant energy of Caribe of Key West at El Meson de Pepes on Mallory Square. This captivating entertainer brings the spirit of Cuban…
Sunset Celebration at Mallory Square
Experience the vibrant Sunset Celebration at Mallory Square in Key West where talented street performers take center stage. Revel in the artistry of jugglers and…
Free
Ericson Holt at Two Friends Patio Restaurant
Experience the captivating performances of Ericson Holt at Two Friends Patio Restaurant. Known for his dynamic musical talent, Ericson's live shows create an enchanting atmosphere…
Free
AstroYeti at Green Parrot Bar
AstroYeti brings an electrifying performance to the iconic Green Parrot Bar in Key West, captivating audiences with their dynamic sound and vibrant energy. Known for…
Free
Preacher Pete Presents at Sloppy Joe’s Bar
Experience the captivating presence of Preacher Pete at Sloppy Joe's Bar, where his warm demeanor and insightful storytelling illuminate the vibrant, historic venue. Known for…
Free
Bria Ansara at Berlin’s Cocktail Bar
Bria Ansara enchants patrons at Berlin's Cocktail Bar with her captivating performance. Her jazz-infused vocals and magnetic stage presence create an unforgettable experience. As guests…
Free
Filming Sit with Kit Podcast Episodes
Join the captivating entertainer Mr. Kit Carson at Angelina's Pizzeria in Key West for the Filming Sit with Kit podcast episodes. Engage in vibrant discussions…
Free
Barrett Thomas at The Alamo Key West
Barrett Thomas is a dynamic musician based in Key West, renowned for his innovative live performances. Using his talent as a looper, he creates captivating…
Free
Dinner with the Dead – Rainbow Full of Sound Waynard in the Grand Piano at Viva Argentinian Steakhouse
Join Waynard Scheller for an unforgettable evening at Viva Argentinian Steakhouse, where his exceptional keyboard skills and vibrant stage presence with Rainbow Full of Sound…
Free
April’s Walk On White
April's Walk On White features captivating live music, creating a dynamic atmosphere for this monthly art walk. Held along picturesque White Street in Key West,…
Free
Terri, Larry and Friends Live Music at William Weech American Legion Post 168
Terri, Larry, and Friends deliver electrifying performances at the William Weech American Legion Post 168 in Key West. Known for their dynamic stage presence, this…
Free
Oren Polak at Irish Kevin’s Bar
Oren Polak captivates audiences at Irish Kevin's Bar with his versatile music and charismatic stage presence. Known for delivering Music for Everyone, Everywhere, his performances…
Free
Andy’s Cabana Open Mic No Mic Night
Andy's Cabana showcases a unique night where talented performers captivate audiences in an intimate environment, relying solely on their pure acoustic sounds. Nestled in Key…
Free
Catch The Mania Trivia at Brady’s Pub
Join the excitement at Brady's Pub for Catch The Mania Trivia, hosted by a dynamic entertainer who brings energy and fun to every question. Enjoy…
Free
Joe The Show at Rick’s Bar Downstairs Stage
Experience the magic of Joe The Show, the hardest working musician in Key West, live at Rick's Bar Downstairs Stage. JTS captivates audiences with his…
Free
Magic Of Frank Everhart at Schooner Wharf Bar
Experience the enchanting Magic of Frank Everhart at the Schooner Wharf Bar in Key West. Celebrated for his innovative illusions and captivating storytelling, Everhart mesmerizes…
Free
Wicked Bingo at The Retro Room
Experience a captivating evening with the lively entertainer at Wicked Bingo in The Retro Room, nestled in Old Town Key West. This nostalgic venue offers…
Free
Nick Brownell at Schooner Wharf Bar
Nick Brownell is a talented musician known for his captivating live performances at Schooner Wharf Bar. His diverse musical repertoire enchants audiences every Thursday evening…
Free
Zach Lovering at Halo Rooftop Lounge Bar at The Saint
Zach Lovering captivates audiences at the Halo Rooftop Lounge Bar in The Saint Hotel with his vibrant performances and soulful melodies. A beloved local musician…
Free
Kristen McNamara at La Te Da
Kristen McNamara, a multifaceted artist, enchants audiences at La Te Da in Key West with her soulful singing and evocative songwriting. Inspired by her love…
Free
Tony Baltimore at Tiki House Key West
Experience the musical artistry of Tony Baltimore at Schooner Wharf Bar in Key West. This talented singer/songwriter blends alternative roots-rock with captivating originality. Raised by…
Free
Amos Gill at Comedy Key West
Amos Gill, a standout Australian comedian, brings his sharp wit and engaging storytelling to Comedy Key West. Known for captivating audiences with hilarious insights and…
$35
AstroYeti at Green Parrot Bar
AstroYeti takes the stage at the iconic Green Parrot Bar in Key West, bringing their unique blend of cosmic sounds to this historic dive bar.…
Free
Randy Roberts at La Te Da
Experience the unparalleled talent of Randy Roberts at La Te Da's cabaret. With over thirty years of captivating performances, Randy's live vocals and charismatic stage…
$35
AstroYeti at Green Parrot Bar
AstroYeti brings a cosmic blend of energetic beats and vibrant melodies to the iconic Green Parrot Bar in Key West. Known for electrifying performances, AstroYeti…
Free
Friday, April 17, 2026
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April 17, 2026 -Yoga on the Beach – Smather’s Beach
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April 17, 2026 -11th Annual Conchy Beach Cleanup
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April 17, 2026 -Fishmonster Max- Daily Party Boat Fishing
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April 17, 2026 -Yoga on the Beach – Ft Zachary Taylor
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April 17, 2026 -Ericson Holt at Two Friends Patio Restaurant
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April 17, 2026 -Tom Curtis Jr at Sloppy Joe’s Bar
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April 17, 2026 -Legends of Key West – The Conch Republic Old Town Walking Tour
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April 17, 2026 -Story Time at the Key West Library
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April 17, 2026 -Andy Westcott at Rams Head Southernmost
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April 17, 2026 -Jeff Harris at Irish Kevin’s Bar
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April 17, 2026 -Distillery Tour – Key West Legal Rum Distillery
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April 17, 2026 -Mojito Class by Key West Legal Rum Distillery – Min 4 people
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April 17, 2026 -Glass Bottom Boat Cruise – Key West’s Window to the Sea
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April 17, 2026 -Elle Haley at Hog’s Breath Saloon
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April 17, 2026 -New Moon Magic w/Mermaid Dorian
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April 17, 2026 -Brian Roberts at Sloppy Joe’s Bar
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April 17, 2026 -Wynn Taylor at Rick’s Bar Downstairs Stage
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April 17, 2026 -Tony Baltimore at Schooner Wharf Bar
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April 17, 2026 -A Pirate Looks Back: Jimmy Buffett Tribute Show at Comedy Key West
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April 17, 2026 -Mike Stack & DLew at Tiki House Key West
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April 17, 2026 -Rick Fusco at Two Friends Patio Restaurant
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April 17, 2026 -Glass Bottom Boat Cruise – Key West’s Window to the Sea
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April 17, 2026 -Fishmonster Max- Daily Party Boat Fishing
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April 17, 2026 -Mylo O’Maolain at Irish Kevin’s Bar
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April 17, 2026 -Reef Snorkeling, Dolphin Watch Eco Tour & Sunset Cruise
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April 17, 2026 -Dead Fest Key West at The Alamo Key West
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April 17, 2026 -Happy Dog at The Alamo Key West
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April 17, 2026 -Joe the Show at Rick’s Bar Downstairs Stage
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April 17, 2026 -Josh Kiser at Mac’s Place
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April 17, 2026 -Glass Bottom Boat Cruise – Key West’s Window to the Sea
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April 17, 2026 -Conch Republic Days Opening Ceremony & Raising of the Colors
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April 17, 2026 -Telephone Tag at Hog’s Breath Saloon
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April 17, 2026 -Joel Nelson at Two Friends Patio Restaurant
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April 17, 2026 -Sunset Celebration at Mallory Square
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April 17, 2026 -World Famous 801 Girls- 5pm Show
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April 17, 2026 -Caribe of Key West at El Meson de Pepes on Mallory Square
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April 17, 2026 -Wynn Taylor at Rams Head Southernmost
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April 17, 2026 -Burning Bridges at Sloppy Joe’s Bar
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April 17, 2026 -The Heavy Pets at Green Parrot Bar
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April 17, 2026 -Cash Bingo at William Weech American Legion Post 168
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April 17, 2026 -Gerd Rube at Tiki House Key West
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April 17, 2026 -NY Pauly at Irish Kevin’s Bar
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April 17, 2026 -42nd Annual Schooner Wharf Kick-Off Party & Conch Shell Blowing Contest
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April 17, 2026 -Guitar Hero Tournament at The Retro Room
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April 17, 2026 -Gulfstream Band at Schooner Wharf Bar
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April 17, 2026 -Magic Of Frank Everhart at Schooner Wharf Bar
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April 17, 2026 -The Fabulous Spectrelles Revue
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April 17, 2026 -New Moon Drum Circle
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April 17, 2026 -Karaoke at Two Friends Patio
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April 17, 2026 -Elle Haley at Rick’s Bar Downstairs Stage
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April 17, 2026 -Kari Wolf at Halo Rooftop Lounge Bar at The Saint
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April 17, 2026 -Kristen McNamara at La Te Da
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April 17, 2026 -Steely Dead at The Alamo Key West
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April 17, 2026 -Amos Gill at Comedy Key West
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April 17, 2026 -Motown Soul City DisFunkshunals at William Weech American Legion Post 168
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April 17, 2026 -Randy Roberts at La Te Da
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April 17, 2026 -The Heavy Pets at Green Parrot Bar
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April 17, 2026 -The Heavy Pets at Green Parrot Bar
Yoga on the Beach – Smather’s Beach
Join an invigorating Yoga on the Beach session at Smathers Beach in Key West. Led by an experienced instructor, you'll find peace and tranquility amidst…
$20
11th Annual Conchy Beach Cleanup
Join the 11th Annual Conchy Beach Cleanup at Higgs Beach and enjoy an exciting day of community service complemented by a captivating entertainer. This family-friendly…
Free
Fishmonster Max- Daily Party Boat Fishing
Join the Fishmonster Max for a daily party boat fishing adventure at A & B Marina in Key West. While the marina offers excellent boating…
$85.00
Yoga on the Beach – Ft Zachary Taylor
Join us for a serene yoga session guided by an inspiring instructor at the picturesque Fort Zachary Taylor State Park in Key West. Amidst historic…
$20
Ericson Holt at Two Friends Patio Restaurant
Experience the dynamic performances of Ericson Holt at Two Friends Patio Restaurant in Key West. A talented musician, Holt captivates audiences with his soulful tunes…
Free
Tom Curtis Jr at Sloppy Joe’s Bar
Tom Curtis Jr captivates audiences at Sloppy Joe's Bar in Key West with his engaging performances. Bringing energy and charisma to the stage, he enhances…
Free
Legends of Key West – The Conch Republic Old Town Walking Tour
Experience the Legends of Key West and the Conch Republic Old Town Walking Tour with Island Audio Tours led by Magic Frank and Josh. These…
Free
Story Time at the Key West Library
Experience a captivating Story Time at the Key West Library, led by a talented and engaging entertainer who brings tales to life with dynamic storytelling…
Free
Andy Westcott at Rams Head Southernmost
Andy Westcott, a talented musician from Key West, is set to captivate audiences at Rams Head Southernmost with his unique sound. With a highly anticipated…
Free
Jeff Harris at Irish Kevin’s Bar
Jeff Harris brings his captivating blend of music and comedy to Irish Kevin's Bar in Key West. As a talented singer, songwriter, and comedian, Jeff…
Free
Distillery Tour – Key West Legal Rum Distillery
Explore the captivating Key West Legal Rum Distillery located in the Historic Seaport, offering an engaging atmosphere with daily free tours and tastings. Delight in…
Free
Mojito Class by Key West Legal Rum Distillery – Min 4 people
Join the Mojito Class at the Key West Legal Rum Distillery, where a talented entertainer guides you through the art of crafting the perfect mojito.…
$75.00
Glass Bottom Boat Cruise – Key West’s Window to the Sea
Join the Glass Bottom Boat Cruise in Key West for a captivating evening of ocean exploration. Highlighting a talented entertainer, the cruise combines marine beauty…
$69.95
Elle Haley at Hog’s Breath Saloon
Elle Haley enchants audiences with her soulful performances at Hog's Breath Saloon in Key West. As a vibrant musician from the Florida Keys, she captivates…
Free
New Moon Magic w/Mermaid Dorian
Experience the enchanting world of Mermaid Dorian at New Moon Magic. Join this captivating entertainer on South Beach for an afternoon of swimming, storytelling, and…
Free
Brian Roberts at Sloppy Joe’s Bar
Brian Roberts, a talented singer/songwriter from the Florida Keys, enchants audiences with his captivating live performances at Sloppy Joe's Bar. His engaging presence and soulful…
Free
Wynn Taylor at Rick’s Bar Downstairs Stage
Wynn Taylor, a charismatic singer-songwriter from Lexington, captivates audiences with his soulful roots music at Rick's Bar Downstairs Stage in Key West. An Army veteran…
Free
Tony Baltimore at Schooner Wharf Bar
Experience the musical artistry of Tony Baltimore at Schooner Wharf Bar in Key West. This talented singer/songwriter blends alternative roots-rock with captivating originality. Raised by…
Free
A Pirate Looks Back: Jimmy Buffett Tribute Show at Comedy Key West
A Pirate Looks Back: Jimmy Buffett Tribute Show at Comedy Key West showcases Caleb Hogan, a distinguished musician and actor who channels the spirit of…
$28
Mike Stack & DLew at Tiki House Key West
Experience the innovative synergy of Mike Stack and DLew at Tiki House Key West. This dynamic duo captivates audiences with their blend of strategic insight…
Free
Rick Fusco at Two Friends Patio Restaurant
Rick Fusco captivates audiences at Two Friends Patio Restaurant with his musical talent, providing an unforgettable live music experience. Set in the vibrant atmosphere of…
Free
Glass Bottom Boat Cruise – Key West’s Window to the Sea
Join the Glass Bottom Boat Cruise in Key West for an unforgettable journey with spectacular views of marine life. The highlight of the cruise is…
$69.95
Fishmonster Max- Daily Party Boat Fishing
Join Fishmonster Max for a thrilling daily party boat fishing adventure at A & B Marina in Key West's historic seaport. While enjoying the vibrant…
$85.00
Mylo O’Maolain at Irish Kevin’s Bar
Experience the charismatic Mylo O’Maolain at Irish Kevin’s Bar in Key West. Known for his captivating performances, Mylo energizes the crowd with lively tunes and…
Free
Reef Snorkeling, Dolphin Watch Eco Tour & Sunset Cruise
Experience an unforgettable aquatic adventure with Reef Snorkeling, Dolphin Watch Eco Tour & Sunset Cruise at Sunset Watersports in Key West. Dive into vibrant coral…
$79.95
Dead Fest Key West at The Alamo Key West
Dead Fest Key West at The Alamo Key West is a vibrant celebration of live music, featuring talented entertainers who light up the outdoor venue.…
Free
Happy Dog at The Alamo Key West
Join the Happy Dog Band at The Alamo Key West for an unforgettable musical journey. Known for their improvisational jam sessions, they capture the essence…
Free
Joe the Show at Rick’s Bar Downstairs Stage
Experience the dynamic energy of Joe the Show at Rick's Bar Downstairs Stage in Key West. Known for his exceptional talent and tireless work ethic,…
Free
Josh Kiser at Mac’s Place
Josh Kiser, a talented Cleveland, Tennessee-born singer-songwriter, will captivate audiences at Mac's Place in Key West. With his unique blend of traditional '90s sounds and…
Free
Glass Bottom Boat Cruise – Key West’s Window to the Sea
Join the Glass Bottom Boat Cruise in Key West and enjoy the mesmerizing views of the ocean beneath you, all while being entertained by talented…
$69.95
Conch Republic Days Opening Ceremony & Raising of the Colors
Celebrate the vibrant Opening Ceremony & Raising of the Colors at Mallory Square, marking the 44th Independence Celebration. The lively event features the Conch Republic…
Free
Telephone Tag at Hog’s Breath Saloon
Experience the quirky and entertaining Telephone Tag at Hog's Breath Saloon, where the art of playful communication takes center stage. This unique entertainer turns missed…
Free
Joel Nelson at Two Friends Patio Restaurant
Experience the vibrant sounds of musician Joel Nelson at Two Friends Patio Restaurant. Nestled in the heart of Key West, this beloved venue offers a…
Free
Sunset Celebration at Mallory Square
Experience the vibrant Sunset Celebration at Mallory Square, where entertainers captivate audiences with their unique artistry. Watch the famous cat man and jugglers perform amidst…
Free
World Famous 801 Girls- 5pm Show
Experience the dazzling performances of the World Famous 801 Girls at their 5pm Show. These talented drag queens captivate audiences at the vibrant 801 Bourbon…
Caribe of Key West at El Meson de Pepes on Mallory Square
Experience the vibrant energy of Caribe of Key West at El Meson de Pepe's on Mallory Square. This talented entertainer brings the authentic sounds of…
Wynn Taylor at Rams Head Southernmost
Experience the captivating sounds of Wynn Taylor, a talented singer-songwriter and proud U.S. Army veteran, at Rams Head Southernmost. Based in Key West, Florida, Wynn…
Free
Burning Bridges at Sloppy Joe’s Bar
Burning Bridges, a dynamic variety band from Upstate SC, brings their high-energy performances to Sloppy Joe's Bar in Key West. Known for an eclectic mix…
Free
The Heavy Pets at Green Parrot Bar
The Heavy Pets bring their vibrant and dynamic sound to the iconic Green Parrot Bar in Key West. Known for their fusion of rock, funk,…
Free
Cash Bingo at William Weech American Legion Post 168
Join the excitement at William Weech American Legion Post 168 for Cash Bingo, where the vibrant online bingo game takes center stage. Experience thrilling gameplay…
Free
Gerd Rube at Tiki House Key West
Experience the enchanting sounds of Gerd Rube, a renowned singer-songwriter from Key West, at Tiki House. With a repertoire spanning over 800 songs, Rube seamlessly…
Free
NY Pauly at Irish Kevin’s Bar
NY Pauly, a legendary performer at Irish Kevin's Bar in Key West, captivates audiences with his dynamic blend of music and entertainment. His vibrant shows…
Free
42nd Annual Schooner Wharf Kick-Off Party & Conch Shell Blowing Contest
Experience the 42nd Annual Schooner Wharf Kick-Off Party & Conch Shell Blowing Contest at the Schooner Wharf Bar, set in Key West's vibrant waterfront. Dance…
Free
Guitar Hero Tournament at The Retro Room
Join the excitement at The Retro Room's Guitar Hero Tournament, where talented entertainers bring nostalgia to life. This unique café in Old Town Key West…
Free
Gulfstream Band at Schooner Wharf Bar
Gulfstream Band brings an electrifying performance to the Schooner Wharf Bar, mesmerizing audiences with their unique blend of genres and innovative sound. Known for pushing…
Free
Magic Of Frank Everhart at Schooner Wharf Bar
At the Schooner Wharf Bar, legendary magician Frank Everhart delivers a mesmerizing performance that captivates audiences with his innovative tricks and compelling storytelling. Renowned for…
Free
The Fabulous Spectrelles Revue
The Fabulous Spectrelles Revue promises an unforgettable evening as they take the stage at 7:00 PM at Kaya Island Eats in Key West. Known for…
Free
New Moon Drum Circle
Experience the mesmerizing rhythms of the New Moon Drum Circle led by a captivating entertainer at The Green House Mothership. This free, 21+ event on…
Free
Karaoke at Two Friends Patio
Join the lively Karaoke at Two Friends Patio, where talented entertainers light up the open-air venue with energetic performances. Located near Mallory Square, this Key…
Free
Elle Haley at Rick’s Bar Downstairs Stage
Elle Haley, a vibrant musician from the Florida Keys, graces the stage at Rick's Bar Downstairs Stage. Known for her captivating performances and soulful tunes,…
Free
Kari Wolf at Halo Rooftop Lounge Bar at The Saint
Kari Wolf, a dynamic musician from Key West, captivates audiences with her soulful melodies and enchanting performances at the Halo Rooftop Lounge Bar at The…
Free
Kristen McNamara at La Te Da
Kristen McNamara captivates audiences at La Te Da in Key West with her soulful singing and evocative songwriting. A multifaceted artist with a gypsy spirit,…
Free
Steely Dead at The Alamo Key West
Steely Dead captivates audiences at The Alamo Key West with their unique fusion of Steely Dan and Grateful Dead tunes. Their energetic performances and impressive…
Free
Amos Gill at Comedy Key West
Amos Gill, a talented Australian comedian renowned for his sharp wit and engaging storytelling, is set to entertain audiences at Comedy Key West. With a…
$35
Motown Soul City DisFunkshunals at William Weech American Legion Post 168
Experience the electrifying performance of Motown Soul City DisFunkshunals at William Weech American Legion Post 168 in Key West. Known for their infectious energy and…
Free
Randy Roberts at La Te Da
Randy Roberts dazzles audiences at La Te Da with his remarkable live performances in Key West. Renowned for his electrifying vocals and captivating impersonations of…
$35
The Heavy Pets at Green Parrot Bar
The Heavy Pets bring their vibrant and dynamic sound to the iconic Green Parrot Bar in Key West. Known for their improvisational rock and jazzy…
Free
The Heavy Pets at Green Parrot Bar
Renowned for their fusion of rock, jazz, and funk, The Heavy Pets are set to electrify the crowd at the Green Parrot Bar in Key…
Free
Saturday, April 18, 2026
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April 18, 2026 -28th Annual Earth Day 5K
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April 18, 2026 -Alfonse at Two Friends Patio Restaurant
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April 18, 2026 -Fishmonster Max- Daily Party Boat Fishing
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April 18, 2026 -Yoga on the Beach – Ft Zachary Taylor
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April 18, 2026 -Native Plant Sale: Grow Your Own Habitat!
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April 18, 2026 -Compost Village: Monthly Compost Drop-Off & Demonstration
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April 18, 2026 -Prime of Life Yoga with Monica Haskell
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April 18, 2026 -Izzy Zaidman at Sloppy Joe’s Bar
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April 18, 2026 -42nd Annual Conch Republic Arts & Craft Duval Street Fair
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April 18, 2026 -Nature is Art: Children’s Art Workshop
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April 18, 2026 -OCEAN & MANGROVE WEEKLY CLEANUP WITH THE CR MARINE ARMY
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April 18, 2026 -Jeff Harris at Irish Kevin’s Bar
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April 18, 2026 -Distillery Tour – Key West Legal Rum Distillery
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April 18, 2026 -Mojito Class by Key West Legal Rum Distillery – Min 4 people
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April 18, 2026 -Glass Bottom Boat Cruise – Key West’s Window to the Sea
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April 18, 2026 -Brian Roberts at Sloppy Joe’s Bar
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April 18, 2026 -Nick Brownell at Schooner Wharf Bar
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April 18, 2026 -Zack Seemiller at Rick’s Bar Downstairs Stage
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April 18, 2026 -Cliff Cody at Hog’s Breath Saloon
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April 18, 2026 -Joel Nelson at Two Friends Patio Restaurant
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April 18, 2026 -A Pirate Looks Back: Jimmy Buffett Tribute Show at Comedy Key West
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April 18, 2026 -Joe The Show at Tiki House Key West
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April 18, 2026 -CONCH CRAWL PUB STROLL ON DUVAL
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April 18, 2026 -Glass Bottom Boat Cruise – Key West’s Window to the Sea
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April 18, 2026 -44th Annual CONCH REPUBLIC DRAG RACES ON DUVAL
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April 18, 2026 -Fishmonster Max- Daily Party Boat Fishing
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April 18, 2026 -NY Pauly at Irish Kevin’s Bar
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April 18, 2026 -Elle Haley at Old Sailor Bar
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April 18, 2026 -Beach clean up
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April 18, 2026 -Beach clean up
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April 18, 2026 -Reef Snorkeling, Dolphin Watch Eco Tour & Sunset Cruise
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April 18, 2026 -Bradd Shadduck at Rick’s Bar Downstairs Stage
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April 18, 2026 -Dead Fest Key West at The Alamo Key West
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April 18, 2026 -Happy Dog at The Alamo Key West
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April 18, 2026 -Conch Republic Rum Launch Party
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April 18, 2026 -Jockey Jord at Two Friends Patio Restaurant
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April 18, 2026 -Glass Bottom Boat Cruise – Key West’s Window to the Sea
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April 18, 2026 -Jack Wolf at Tiki House Key West
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April 18, 2026 -Telephone Tag at Hog’s Breath Saloon
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April 18, 2026 -Sunset Celebration at Mallory Square
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April 18, 2026 -World Famous 801 Girls- 5pm Show
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April 18, 2026 -Caribe of Key West at El Meson de Pepes on Mallory Square
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April 18, 2026 -Charlie Miller at Rams Head Southernmost
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April 18, 2026 -Jerrod Isaman at Mac’s Place
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April 18, 2026 -The Heavy Pets at Green Parrot Bar
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April 18, 2026 -Victoria Leigh at Sloppy Joe’s Bar
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April 18, 2026 -Joe The Show at Durty Harry’s Stage
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April 18, 2026 -Irish Kevin at Irish Kevin’s Bar
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April 18, 2026 -DJ Of Course Dave at The Retro Room
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April 18, 2026 -Magic Of Frank Everhart at Schooner Wharf Bar
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April 18, 2026 -Skidaddles Band at Schooner Wharf Bar
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April 18, 2026 -Karaoke at Two Friends Patio
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April 18, 2026 -Michael Corleto at Rick’s Bar Downstairs Stage
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April 18, 2026 -Ronnie & Gregory at La Te Da
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April 18, 2026 -Steely Dead at The Alamo Key West
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April 18, 2026 -Thomas Barrett at Halo Rooftop Lounge Bar at The Saint
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April 18, 2026 -Amos Gill at Comedy Key West
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April 18, 2026 -Elle Haley with Aaron at Hank’s Hair of the Dog Saloon
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April 18, 2026 -Randy Roberts at La Te Da
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April 18, 2026 -The Heavy Pets at Green Parrot Bar
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April 18, 2026 -The Heavy Pets at Green Parrot Bar
28th Annual Earth Day 5K
Join the 28th Annual Earth Day 5K at Truman Waterfront Park in Key West, where participants support the Conch Republic Marine Army's initiatives. Enjoy the…
Free
Alfonse at Two Friends Patio Restaurant
Experience the captivating music of Alfonse at Two Friends Patio Restaurant, a beloved Key West spot since 1967. Renowned for its open-air setting near Mallory…
Free
Fishmonster Max- Daily Party Boat Fishing
Join the Fishmonster Max daily party boat fishing adventure at A & B Marina in Key West's historic seaport. Enjoy a vibrant atmosphere with live…
$85.00
Yoga on the Beach – Ft Zachary Taylor
Join Yoga on the Beach at Fort Zachary Taylor State Park in Key West for an invigorating experience amidst breathtaking sunset views. Enhance your well-being…
$20
Native Plant Sale: Grow Your Own Habitat!
Join the Native Plant Sale at Key West Tropical Forest & Botanical Garden for a vibrant celebration of nature. Enjoy a Prime of Life Yoga…
Free
Compost Village: Monthly Compost Drop-Off & Demonstration
Join us at Compost Village for a monthly compost drop-off and demonstration, where the highlight is the engaging UF/IFAS Master Gardeners. Their captivating hands-on demonstrations…
Free
Prime of Life Yoga with Monica Haskell
Join Monica Haskell for an invigorating Prime of Life Yoga session at the beautiful Key West Tropical Forest & Botanical Garden. Monica, a celebrated yoga…
$20
Izzy Zaidman at Sloppy Joe’s Bar
At Sloppy Joe's Bar, Izzy Zaidman transforms the historic Key West venue into an electrifying musical haven. As a guitarist, composer, and singer-songwriter, Izzy captivates…
Free
42nd Annual Conch Republic Arts & Craft Duval Street Fair
The 42nd Annual Conch Republic Arts & Craft Duval Street Fair transforms Duval Street into a lively celebration of creativity, featuring live music and entertainment…
Free
Nature is Art: Children’s Art Workshop
Join the enchanting Nature is Art: Children’s Art Workshop, where talented facilitators from the Key West Art & Historical Society guide children through creative adventures…
Free
OCEAN & MANGROVE WEEKLY CLEANUP WITH THE CR MARINE ARMY
Join the CR Marine Army for their Ocean & Mangrove Weekly Cleanup, departing from Perry Hotel Marina and Isla Bella Resort. Participate in preserving Florida…
Free
Jeff Harris at Irish Kevin’s Bar
At Irish Kevin's Bar, Jeff Harris captivates audiences with his dynamic performances that blend music and comedy. A talented singer-songwriter and comedian, Jeff enchants with…
Free
Distillery Tour – Key West Legal Rum Distillery
Experience the vibrant nightlife atmosphere at Key West First Legal Rum Distillery. Enjoy free daily tours and tastings in this historic seaport location, once a…
Free
Mojito Class by Key West Legal Rum Distillery – Min 4 people
Join the Mojito Class at Key West Legal Rum Distillery with a minimum of four people for an unforgettable experience. Enjoy lively entertainment as expert…
$75.00
Glass Bottom Boat Cruise – Key West’s Window to the Sea
Experience the Glass Bottom Boat Cruise in Key West, where a charming entertainer guides you through the vibrant marine life visible beneath your feet. With…
$69.95
Brian Roberts at Sloppy Joe’s Bar
Experience the captivating performances of singer/songwriter Brian Roberts at Sloppy Joe's Bar in Key West. A talented musician based in the Florida Keys, Brian enchants…
Free
Nick Brownell at Schooner Wharf Bar
Nick Brownell is a talented Key West musician renowned for his captivating live performances. Catch him at Schooner Wharf Bar, where he delivers a diverse…
Free
Zack Seemiller at Rick’s Bar Downstairs Stage
Zack Seemiller takes the stage at Rick's Bar Downstairs Stage, captivating audiences with his dynamic presence and soulful music. An accomplished musician and songwriter, Zack's…
Free
Cliff Cody at Hog’s Breath Saloon
Experience the powerful voice and heartfelt storytelling of Cliff Cody at Hog's Breath Saloon. This Texas-born, Key West-based indie country singer/songwriter blends classic country themes…
Free
Joel Nelson at Two Friends Patio Restaurant
Experience the captivating performance of Joel Nelson, a talented musician, at Two Friends Patio Restaurant. Known for his engaging presence and versatile musical repertoire, Joel…
Free
A Pirate Looks Back: Jimmy Buffett Tribute Show at Comedy Key West
Experience the charismatic tribute to the legendary Jimmy Buffett at Comedy Key West, starring the exceptional Caleb Hogan. Vibrant and engaging, Hogan embodies Buffett, delivering…
$28
Joe The Show at Tiki House Key West
Experience an unforgettable night with Joe The Show at Tiki House Key West. Known for his dynamic energy and tireless work ethic, Joe captivates audiences…
Free
CONCH CRAWL PUB STROLL ON DUVAL
Join the Conch Crawl Pub Stroll on Duval, where vibrant entertainers create unforgettable moments at eight historic saloons. Experience the lively bars and soulful tunes…
Free
Glass Bottom Boat Cruise – Key West’s Window to the Sea
Embark on the Glass Bottom Boat Cruise in Key West where the stars of the show are the vibrant marine life visible through the crystal-clear…
$69.95
44th Annual CONCH REPUBLIC DRAG RACES ON DUVAL
Join the lively 44th Annual Conch Republic Drag Races on Duval at Bourbon Street Pub. This vibrant event highlights dazzling drag queens showcasing their charisma…
Free
Fishmonster Max- Daily Party Boat Fishing
Join Fishmonster Max for daily party boat fishing at A & B Marina in Key West's historic seaport. Enjoy the beautiful waterfront and lively atmosphere,…
$85.00
NY Pauly at Irish Kevin’s Bar
NY Pauly is the charismatic heart of Irish Kevin's Bar in Key West. Renowned for his engaging performances, he seamlessly combines music and entertainment, captivating…
Free
Elle Haley at Old Sailor Bar
Elle Haley captivates audiences at the Old Sailor Bar with her soulful tunes, bringing vibrant energy to the heart of Key West. As a renowned…
Free
Beach clean up
Join the Beach Clean Up at Higgs Beach in Key West for a day of fun and purpose. Enjoy the beautiful scenery while assisting conservation…
Free
Beach clean up
Join us at Higgs Beach in Key West for a cleanup event with live performances that will keep you entertained while contributing to a great…
Free
Reef Snorkeling, Dolphin Watch Eco Tour & Sunset Cruise
Join Sunset Watersports in Key West's Historic Seaport for an unforgettable adventure. Although details about the entertainer are sparse, the experienced staff ensures a thrilling…
$79.95
Bradd Shadduck at Rick’s Bar Downstairs Stage
Bradd Shadduck lights up the stage at Rick's Bar Downstairs in Key West with his electrifying performance. As a talented musician, Shadduck captivates the audience…
Free
Dead Fest Key West at The Alamo Key West
Dead Fest Key West at The Alamo Key West features an exceptional lineup of talented musicians, creating an unforgettable live music experience. Set in the…
Free
Happy Dog at The Alamo Key West
Experience the captivating sounds of the Happy Dog Band at The Alamo Key West. This improvisational jam band channels the essence of the psychedelic era,…
Free
Conch Republic Rum Launch Party
Experience the Conch Republic Rum Launch Party at the Bali Bar, featuring captivating music by Sir CW Colt, the Minstrel of the Conch Republic. Enjoy…
Free
Jockey Jord at Two Friends Patio Restaurant
Experience the vibrant sounds of Jockey Jord at Two Friends Patio Restaurant. This talented musician captivates audiences with dynamic performances amidst Key West's lively atmosphere.…
Free
Glass Bottom Boat Cruise – Key West’s Window to the Sea
Join us for the Glass Bottom Boat Cruise in Key West, a unique journey showcasing the magical underwater world. Delight in live entertainment that enhances…
$69.95
Jack Wolf at Tiki House Key West
Experience the soulful performances of Jack Wolf at Tiki House Key West. This talented singer-songwriter captivates audiences with his heartfelt melodies, reflecting his life's passions…
Free
Telephone Tag at Hog’s Breath Saloon
Experience the entertaining antics of Telephone Tag at Hog's Breath Saloon in Key West's Mallory Square District. This unique performer invites you into a playful…
Free
Sunset Celebration at Mallory Square
Experience the captivating Sunset Celebration at Mallory Square, where vibrant street performers steal the show. Marvel at the famous cat man and talented jugglers as…
Free
World Famous 801 Girls- 5pm Show
Experience the dazzling energy of the World Famous 801 Girls at their exclusive 5pm show. These exceptional drag queens bring charisma, uniqueness, and flair to…
Caribe of Key West at El Meson de Pepes on Mallory Square
Experience the vibrant sounds of Caribe of Key West, performing live at El Meson de Pepe’s on Mallory Square. This family-owned establishment in Key West…
Charlie Miller at Rams Head Southernmost
Charlie Miller, a dynamic musician and adventurous sailor, captivates audiences at Rams Head Southernmost with his spirited performances. Embodying the essence of a modern-day pirate…
Free
Jerrod Isaman at Mac’s Place
Jerrod Isaman, a dynamic entrepreneur and technology expert, brings his innovative flair to Mac's Place, a lively waterfront sports bar in Key West. Known for…
Free
The Heavy Pets at Green Parrot Bar
Experience the electrifying sounds of The Heavy Pets at the iconic Green Parrot Bar in Key West. Known for their jam-infused rock, this talented band…
Free
Victoria Leigh at Sloppy Joe’s Bar
Victoria Leigh brings her energetic performances to Sloppy Joe's Bar, a Key West staple. Known for her engaging presence and musical talent, she captivates audiences…
Free
Joe The Show at Durty Harry’s Stage
Joe The Show, affectionately known as JTS, captivates audiences at Durty Harry's Stage with his dynamic energy and exceptional talent. Renowned for his tireless work…
Free
Irish Kevin at Irish Kevin’s Bar
Irish Kevin is a charismatic and humorous entertainer at Irish Kevin's Bar in Key West. Known for his genuine charm and engaging performances, he captivates…
Free
DJ Of Course Dave at The Retro Room
DJ Of Course Dave brings his vibrant energy and eclectic beats to The Retro Room, creating an unforgettable experience for music lovers. Known for his…
Free
Magic Of Frank Everhart at Schooner Wharf Bar
At the Schooner Wharf Bar, legendary magician Frank Everhart enchants audiences with his mesmerizing performances. Known for his innovative tricks and captivating storytelling, Everhart blends…
Free
Skidaddles Band at Schooner Wharf Bar
Skidaddles Band captivates audiences at Schooner Wharf Bar with their eclectic sound, fusing rock, blues, and folk influences. Known for powerful vocals and skillful instrumentals,…
Free
Karaoke at Two Friends Patio
Experience an unforgettable evening at Two Friends Patio with lively karaoke entertainment stealing the spotlight. Hosted by charismatic entertainers, karaoke nights promise joy and laughter…
Free
Michael Corleto at Rick’s Bar Downstairs Stage
Michael Corleto, a gifted singer-songwriter and multi-instrumentalist from Maine, takes the stage at Rick's Bar in Key West. Renowned for his heartfelt lyrics and rich…
Free
Ronnie & Gregory at La Te Da
Ronnie and Gregory captivate audiences at La Te Da with their dynamic performances, blending creativity and practicality in an inspiring and engaging showcase. Their vibrant…
Free
Steely Dead at The Alamo Key West
Experience a captivating night with Steely Dead at The Alamo Key West. This talented band blends the iconic sounds of Steely Dan with the electrifying…
Free
Thomas Barrett at Halo Rooftop Lounge Bar at The Saint
Experience an unforgettable evening with Thomas Barrett at the Halo Rooftop Lounge Bar at The Saint. Known for his captivating performances, Barrett elevates the evening…
Free
Amos Gill at Comedy Key West
Amos Gill is an acclaimed Australian comedian celebrated for his sharp wit and engaging storytelling. With a charismatic stage presence, he captivates audiences globally, delivering…
$35
Elle Haley with Aaron at Hank’s Hair of the Dog Saloon
Elle Haley, an enchanting musician from the Florida Keys, is set to deliver a mesmerizing performance at Hank's Hair of the Dog Saloon. Known for…
Free
Randy Roberts at La Te Da
Randy Roberts captivates audiences at La Te Da with his exceptional live performances. A true icon in Key West, Randy mesmerizes with astonishing vocal renditions…
$35
The Heavy Pets at Green Parrot Bar
The Heavy Pets bring their energetic and dynamic live performance to the Green Parrot Bar, a historic dive bar in Key West. Known for their…
Free
The Heavy Pets at Green Parrot Bar
Experience an unforgettable night with The Heavy Pets at the iconic Green Parrot Bar in Key West. Known for their electrifying live performances, The Heavy…
Free
Sunday, April 19, 2026
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April 19, 2026 -Tunaskin Island Clean Up | Key West
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April 19, 2026 -Fishmonster Max- Daily Party Boat Fishing
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April 19, 2026 -Yoga on the Beach – Ft Zachary Taylor
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April 19, 2026 -Chris at Two Friends Patio Restaurant
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April 19, 2026 -Key West Artisan Market at Higgs Beach
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April 19, 2026 -Victoria Leigh at Sloppy Joe’s Bar
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April 19, 2026 -KW ARTISAN MARKET – EARTH DAY EDITION
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April 19, 2026 -Bradd Shadduck at Irish Kevin’s Bar
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April 19, 2026 -Marjory Lee at Rams Head Southernmost
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April 19, 2026 -Cow Key Bridge Run – Key West Zero K! | Cowless In Wonderland
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April 19, 2026 -Mojito Class by Key West Legal Rum Distillery – Min 4 people
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April 19, 2026 -Distillery Tour – Key West Legal Rum Distillery
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April 19, 2026 -Glass Bottom Boat Cruise – Key West’s Window to the Sea
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April 19, 2026 -Aaron Blumer at Hog’s Breath Saloon
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April 19, 2026 -Harley Ray at Rick’s Downstairs Stage
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April 19, 2026 -Mylo O’Maolain at Schooner Wharf Bar
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April 19, 2026 -Sid The Bayou Kid at Sloppy Joe’s Bar
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April 19, 2026 -Cow Key Bridge ZERO-K Run
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April 19, 2026 -COW KEY CHANNEL BRIDGE ZERO-K
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April 19, 2026 -Rick Fusco at Two Friends Patio Restaurant
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April 19, 2026 -Mike Emerson Jazz Quartet at Green Parrot Bar
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April 19, 2026 -Golden Cow Awards Ceremony
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April 19, 2026 -Glass Bottom Boat Cruise – Key West’s Window to the Sea
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April 19, 2026 -Aaron Hudgins at Tiki House Key West
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April 19, 2026 -Jeff Harris at Irish Kevin’s Bar
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April 19, 2026 -Mike Emerson Jazz Quartet at Green Parrot Bar
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April 19, 2026 -Reef Snorkeling, Dolphin Watch Eco Tour & Sunset Cruise
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April 19, 2026 -Tea Dance at La Te Da
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April 19, 2026 -801 Karaoke – Hosted by Jeff
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April 19, 2026 -Dave Minninberg at Mac’s Place
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April 19, 2026 -Dead Fest Key West at The Alamo Key West
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April 19, 2026 -Happy Dog at The Alamo Key West
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April 19, 2026 -Trenton Chandler at Rick’s Bar Downstairs Stage
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April 19, 2026 -Glass Bottom Boat Cruise – Key West’s Window to the Sea
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April 19, 2026 -Ross Brown Duo at Hog’s Breath Saloon
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April 19, 2026 -Sunday Jazz at the Gardens
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April 19, 2026 -Caribe of Key West at El Meson de Pepes on Mallory Square
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April 19, 2026 -QMitch Drag Queen Bingo at 22&Co
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April 19, 2026 -Sunset Celebration at Mallory Square
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April 19, 2026 -World Famous 801 Girls- 5pm Show
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April 19, 2026 -Rick Fusco at Rams Head Southernmost
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April 19, 2026 -JAZZ IN THE GARDENS
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April 19, 2026 -Shanty Hounds at Two Friends Patio Restaurant
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April 19, 2026 -Pete & Larry Sloppy 2nds at Sloppy Joe’s Bar
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April 19, 2026 -The Heavy Pets Soundcheck Set at Green Parrot Bar
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April 19, 2026 -Oren Polak at Irish Kevin’s Bar
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April 19, 2026 -CONCH DELIGHT CULTURAL DINNER UNER THE STARS
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April 19, 2026 -80s & 90s Trivia Night
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April 19, 2026 -Jesse & Jillian at Schooner Wharf Bar
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April 19, 2026 -Aaron Hudgins at Rick’s Bar Downstairs Stage
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April 19, 2026 -Elle Haley at Tiki House Key West
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April 19, 2026 -Jack Wolf at Halo Rooftop Lounge Bar at The Saint
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April 19, 2026 -Magic Of Frank Everhart at Schooner Wharf Bar
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April 19, 2026 -Ronnie Lovely at La Te Da
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April 19, 2026 -Steely Dead at The Alamo Key West
Tunaskin Island Clean Up | Key West
Experience the vibrant energy of the Tunaskin Island Clean Up in Key West on April 19th. After joining fellow volunteers to help beautify the island,…
Free
Fishmonster Max- Daily Party Boat Fishing
Join Fishmonster Max for a daily party boat fishing experience at A & B Marina in Key West's historic seaport. Enjoy live entertainment amidst the…
$85.00
Yoga on the Beach – Ft Zachary Taylor
Yoga on the Beach at Fort Zachary Taylor in Key West provides a serene setting with historic charm and stunning ocean views. The real highlight…
$20
Chris at Two Friends Patio Restaurant
Join Chris at Two Friends Patio Restaurant for an unforgettable evening in Key West. Enjoy the lively ambiance of Duval Street while Chris fills the…
Free
Key West Artisan Market at Higgs Beach
The Key West Artisan Market at Higgs Beach offers a vibrant atmosphere with the highlight being live entertainment. Visitors can enjoy performances amid the picturesque…
Victoria Leigh at Sloppy Joe’s Bar
Victoria Leigh captivates audiences at Sloppy Joe's Bar with her vibrant musical performances. Based in the Florida Keys, she delivers feel-good covers, creative mashups, and…
Free
KW ARTISAN MARKET – EARTH DAY EDITION
Experience the KW Artisan Market Earth Day Edition at Higgs Beach, a vibrant celebration featuring local artists and specialty foods. The highlight is the live…
Free
Bradd Shadduck at Irish Kevin’s Bar
Bradd Shadduck brings dynamic performances to Irish Kevin's Bar, captivating audiences with his musical talent. Known for his engaging style, Bradd creates an unforgettable atmosphere…
Free
Marjory Lee at Rams Head Southernmost
Marjory Lee, a captivating musician from Key West, enchants audiences with her soulful voice and expert guitar skills at Rams Head Southernmost. As the Fantasy…
Free
Cow Key Bridge Run – Key West Zero K! | Cowless In Wonderland
The Cow Key Bridge Run - Key West Zero K! is an eccentric spectacle featuring the vibrant Conch Republic Cowntina Moo-sers Party. Enjoy dazzling performances,…
Free
Mojito Class by Key West Legal Rum Distillery – Min 4 people
Join the Mojito Class at Key West Legal Rum Distillery with a minimum group of four. The entertainer, a spirited mixologist, will guide you through…
$75.00
Distillery Tour – Key West Legal Rum Distillery
Experience the vibrant Key West Legal Rum Distillery with daily free tours and tastings. Although there’s no specific entertainer mentioned, the lively setting itself offers…
Free
Glass Bottom Boat Cruise – Key West’s Window to the Sea
Join the Glass Bottom Boat Cruise for a unique maritime experience in Key West. While the tour offers breathtaking views of vibrant marine life through…
$69.95
Aaron Blumer at Hog’s Breath Saloon
Aaron Blumer captivates audiences at Hog's Breath Saloon with his free-spirited, adventurous nature. Known for his spontaneous performances, Blumer seamlessly blends exploration with music, leaving…
Free
Harley Ray at Rick’s Downstairs Stage
Experience the captivating artistry of Harley Ray at Rick's Downstairs Stage. Known for his passionate and innovative songwriting, Ray delivers melodies and lyrics that deeply…
Free
Mylo O’Maolain at Schooner Wharf Bar
Mylo O'Maolain, an enchanting Irish-born musician, lights up Schooner Wharf Bar in Key West with his dynamic performances. Fusing Irish traditions with modern flair, his…
Free
Sid The Bayou Kid at Sloppy Joe’s Bar
Sid The Bayou Kid, a vibrant Louisiana native, enchants audiences at Sloppy Joe's Bar with his spirited tales and blues harmonica skills. This local legend…
Free
Cow Key Bridge ZERO-K Run
The Cow Key Bridge ZERO-K Run on April 19, 2026, promises a whimsical Cowless in Wonderland theme in Key West. This family-friendly event is a…
Free
COW KEY CHANNEL BRIDGE ZERO-K
COW KEY CHANNEL BRIDGE ZERO-K features a charming Zero K run across the Cow Key Bridge in Key West. While details about a specific entertainer…
Free
Rick Fusco at Two Friends Patio Restaurant
Rick Fusco captivates audiences at Two Friends Patio Restaurant with his mesmerizing musical performances. His talent enhances the vibrant atmosphere of this iconic Key West…
Free
Mike Emerson Jazz Quartet at Green Parrot Bar
Experience the dynamic rhythms of the Mike Emerson Jazz Quartet at Green Parrot Bar, where exceptional jazz talents come alive. Known for their captivating performances,…
Free
Golden Cow Awards Ceremony
At the Golden Cow Awards Ceremony, enjoy an unforgettable performance by the Conch Republic's royal minstrel, Sir CW Colt. The event at Key West Sailing…
Free
Glass Bottom Boat Cruise – Key West’s Window to the Sea
Experience the vibrant marine life of Key West aboard the Glass Bottom Boat Cruise, featuring captivating performances by talented local entertainers. This unique excursion combines…
$69.95
Aaron Hudgins at Tiki House Key West
Experience the captivating performances of musician Aaron Hudgins at Tiki House Key West. Known for his engaging live music, Aaron brings vibrant energy to the…
Free
Jeff Harris at Irish Kevin’s Bar
Experience the vibrant performances of Jeff Harris at Irish Kevin's Bar in Key West. An acclaimed singer, songwriter, and comedian, Jeff captivates audiences with his…
Free
Mike Emerson Jazz Quartet at Green Parrot Bar
The Mike Emerson Jazz Quartet captivates audiences at Green Parrot Bar with their dynamic and soulful performances. Known for his remarkable improvisation and vibrant stage…
Free
Reef Snorkeling, Dolphin Watch Eco Tour & Sunset Cruise
Experience the vibrant Reef Snorkeling, Dolphin Watch Eco Tour & Sunset Cruise at Sunset Watersports in Key West's Historic Seaport. Dive into an adventure with…
$79.95
Tea Dance at La Te Da
Experience an unforgettable evening at the Tea Dance at La Te Da in Key West. Enjoy the captivating performances of talented drag queen Randy Roberts,…
Free
801 Karaoke – Hosted by Jeff
Join the lively atmosphere at 801 Bourbon Bar's Karaoke night hosted by the charismatic Jeff. Nestled in Old Town Key West, Jeff's dynamic energy makes…
Free
Dave Minninberg at Mac’s Place
Dave Minninberg brings his captivating performance to Mac's Place, a lively waterfront sports bar in Key West. Known for his engaging stage presence and musical…
Free
Dead Fest Key West at The Alamo Key West
Dead Fest Key West at The Alamo showcases electrifying live performances in a lively outdoor setting. As a prominent entertainer takes the stage, attendees can…
Free
Happy Dog at The Alamo Key West
Experience the electrifying performance of Happy Dog Band at The Alamo Key West. This improvisational jam band captures the essence of the psychedelic era, inviting…
Free
Trenton Chandler at Rick’s Bar Downstairs Stage
Trenton Chandler, a country musician hailing from Shallowater, Texas, brings the essence of West Texas to life on Rick's Bar Downstairs Stage. Influenced by legends…
Free
Glass Bottom Boat Cruise – Key West’s Window to the Sea
Embark on the Glass Bottom Boat Cruise in Key West, where the ocean comes alive beneath your feet. Marvel at the vibrant marine life through…
$69.95
Ross Brown Duo at Hog’s Breath Saloon
Experience the captivating performance of the Ross Brown Duo at Hog's Breath Saloon. Based in Key West, Ross Brown is a versatile musician whose dynamic…
Free
Sunday Jazz at the Gardens
Experience the enchanting Sunday Jazz at the Gardens, where the spotlight shines on renowned jazz performers amidst the lush, tropical backdrop of The Gardens Hotel.…
Free
Caribe of Key West at El Meson de Pepes on Mallory Square
Caribe of Key West enchants audiences at El Meson de Pepe's on Mallory Square. Known for their captivating live performances, Caribe infuses the vibrant Cuban…
QMitch Drag Queen Bingo at 22&Co
Experience the vibrant world of QMitch Drag Queen Bingo at 22&Co in Old Town Key West. Known for unforgettable performances, QMitch dazzles with charisma and…
Free
Sunset Celebration at Mallory Square
Experience the vibrant Sunset Celebration at Mallory Square in Key West, where the famous cat man and other street performers captivate audiences against a stunning…
Free
World Famous 801 Girls- 5pm Show
The World Famous 801 Girls deliver an electrifying 5pm drag show at the iconic 801 Bourbon Bar in Key West. Known for their charismatic performances…
Rick Fusco at Rams Head Southernmost
Rick Fusco, a talented musician, captivates audiences at Rams Head Southernmost with his engaging performances. Known for his dynamic presence and soulful tunes, Fusco creates…
Free
JAZZ IN THE GARDENS
Jazz in the Gardens at The Gardens Hotel features world-renowned jazz artists set in a captivating tropical garden environment. Guests can enjoy live performances while…
Free
Shanty Hounds at Two Friends Patio Restaurant
Shanty Hounds, an inventive acoustic duo featuring Dani Hoy and Key West Chris Rehm, brings lively performances to Two Friends Patio Restaurant. Based in Key…
Free
Pete & Larry Sloppy 2nds at Sloppy Joe’s Bar
Pete & Larry Sloppy 2nds are a dynamic musical duo captivating audiences at Sloppy Joe's Bar in Key West. With their eclectic style, they blend…
Free
The Heavy Pets Soundcheck Set at Green Parrot Bar
The Heavy Pets deliver an electrifying performance at the Green Parrot Bar, captivating the audience with their dynamic sound and infectious energy. Known for their…
Free
Oren Polak at Irish Kevin’s Bar
Oren Polak captivates audiences at Irish Kevin's Bar with his versatile music and charismatic stage presence. Known for delivering Music for Everyone, Everywhere, his performances…
Free
CONCH DELIGHT CULTURAL DINNER UNER THE STARS
Experience a delightful evening at Grimal Grove's Conch Delight Cultural Dinner Under the Stars. Savor exquisite Cuban, Bahamian, and Caribbean dishes crafted by French-trained chef…
Free
80s & 90s Trivia Night
Join us for an unforgettable 80s & 90s Trivia Night at The Retro Room, featuring an engaging entertainer who will take you on a nostalgic…
Free
Jesse & Jillian at Schooner Wharf Bar
Join the dynamic duo Jesse & Jillian, also known as The Happy Dog, at Schooner Wharf Bar for an unforgettable evening of music and laughter.…
Free
Aaron Hudgins at Rick’s Bar Downstairs Stage
Experience the captivating performance of Aaron Hudgins at Rick's Bar Downstairs Stage. Known for his dynamic presence and musical talent, Aaron delivers an unforgettable live…
Free
Elle Haley at Tiki House Key West
Experience the vibrant musical talent of Elle Haley at Tiki House Key West. A dynamic musician from the Florida Keys, Elle captivates audiences with her…
Free
Jack Wolf at Halo Rooftop Lounge Bar at The Saint
Experience the soulful sounds of Jack Wolf at Halo Rooftop Lounge Bar at The Saint. A gifted singer-songwriter based in Key West, Jack enchants audiences…
Free
Magic Of Frank Everhart at Schooner Wharf Bar
Experience the enchanting Magic of Frank Everhart at Schooner Wharf Bar, where this legendary magician captivates audiences with his innovative illusions and captivating storytelling. Renowned…
Free
Ronnie Lovely at La Te Da
Experience the vibrant talent of Ronnie Lovely at La Te Da in Key West. Known for their captivating performances, Ronnie brings a unique flair to…
Free
Steely Dead at The Alamo Key West
Steely Dead brings a dynamic fusion of rock and blues-inspired performances to The Alamo Key West. Known for their captivating live shows, this talented band…
Free