Week of Events
Aaron Blumer at Hog’s Breath Saloon
Experience an unforgettable evening with musician Aaron Blumer at Hog's Breath Saloon, located in Key West's bustling Mallory Square District. Known for his captivating performances,…
Sheldon Benton at Hog’s Breath Saloon
Sheldon Benton captivates audiences at Hog's Breath Saloon with his electrifying live performances. Known for his dynamic sound, Sheldon infuses the lively Key West atmosphere…
DJ Marty ~ Red Garter Saloon Stage
Experience an electrifying night with DJ Marty at the Red Garter Saloon Stage, located within Rick's Entertainment Complex in Key West. Known for his dynamic…
DJ Kori ~ Rick’s Bar Upstairs Stage
Experience an electrifying night with DJ Kori on the Upstairs Stage at Rick's Bar. Known for her dynamic mixes and captivating beats, DJ Kori transforms…
DURTBAGS~ Durty Harry’s Stage
Experience the electrifying energy of The Durtbags, Key West's premier party and rock band, at Durty Harry's Stage. Performing every Thursday through Sunday, The Durtbags…
Tim Williams Band at Hog’s Breath Saloon
Catch the electrifying Tim Williams Band at Hog's Breath Saloon, where their dynamic performances and infectious energy create an unforgettable musical experience. Set in Key…
Karaoke at Bobby’s Monkey Bar
Join the vibrant scene at Bobby's Monkey Bar in Old Town Key West for an unforgettable karaoke night. The spirited entertainer keeps the energy high,…
Mylo O’Maolain at Irish Kevin’s Bar
Experience the vibrant energy of Mylo O'Maolain at Irish Kevin’s Bar. A captivating musician known for engaging performances, Mylo combines lively tunes with audience interaction,…
Karaoke w/ Jason ~ Rick’s Bar Downstairs Stage
Join Jason for an unforgettable karaoke experience at Rick's Bar Downstairs Stage. As the heart and soul of the night, Jason brings infectious energy that…
Zack Seemiller at Hog’s Breath Saloon
Experience the dynamic sounds of Zack Seemiller at Hog's Breath Saloon, where his captivating performance adds an electrifying vibe to the lively Key West venue.…
Dan Harvey Duo at Hog’s Breath Saloon
Experience the vibrant sounds of the Dan Harvey Duo at Hog's Breath Saloon in Key West's Mallory Square District. Renowned for their electrifying live performances,…
Martini Monday at Virgilios
Experience Martini Monday at Virgilio's, where the talented musician Jay Klein captivates the crowd with his live performances. Set in Key West's premier martini bar,…
DJ Marty ~ Red Garter Saloon Stage
Experience the electrifying beats of DJ Marty at the Red Garter Saloon Stage within Rick's Entertainment Complex. Renowned for his dynamic mixes and infectious energy,…
DJ Duke ~ Rick’s Bar Upstairs Stage
Experience an unforgettable night with DJ Duke at the Upstairs Stage of Rick's Bar in Key West. Known for his electrifying beats and dynamic style,…
HYPER DRIVE ~ Durty Harry’s Stage
Experience the electrifying performance of Hyper Drive at Durty Harry's Stage in Rick's Entertainment Complex. As the dynamic band takes the spotlight, immerse yourself in…
Alex Anthony Band at Hog’s Breath Saloon
Experience the electrifying performance of the Alex Anthony Band at Hog's Breath Saloon. Known for their captivating stage presence and musical prowess, the band brings…
Electroniconch at General Horseplay
Electroniconch brings electrifying energy to General Horseplay, captivating audiences with their dynamic performances. In the heart of Old Town Key West on Duval Street, this…
Karaoke at Bobby’s Monkey Bar
Join the vibrant scene at Bobby's Monkey Bar in Old Town Key West for an unforgettable karaoke night. The spirited entertainer keeps the energy high,…
Mylo O’Maolain at Irish Kevin’s Bar
Mylo O'Maolain lights up Irish Kevin's Bar in Key West with his captivating musical talents. Known for engaging performances that invite audience participation, Mylo creates…
Eric Aardema at Hog’s Breath Saloon
Experience the captivating energy of Eric Aardema at Hog's Breath Saloon in Key West's Mallory Square District. Known for his dynamic performances and charismatic stage…
Dan Harvey Duo at Hog’s Breath Saloon
Dan Harvey Duo brings an electrifying performance to Hog's Breath Saloon in Key West, offering a captivating live music experience. With Dan Harvey's exceptional musical…
DJ Todd ~ Red Garter Saloon Stage
DJ Todd electrifies the Red Garter Saloon Stage with his dynamic beats, creating an unforgettable experience at Rick's Entertainment Complex. Known for his eclectic mixes…
DJ Duke ~ Rick’s Bar Upstairs Stage
Experience the electrifying sounds of DJ Duke on the Upstairs Stage at Rick's Bar. Known for his dynamic beats and infectious energy, DJ Duke transforms…
LUVBOM ~ Durty Harry’s Stage
LUVBOM electrifies the stage at Durty Harry's in Rick's Entertainment Complex, Key West's nightlife hub. This standout band captivates with their dynamic performances, merging rock…
Alex Anthony Band at Hog’s Breath Saloon
Experience the vibrant sounds of the Alex Anthony Band at Hog's Breath Saloon in Key West. Known for their energetic performances, the band captivates audiences…
Karaoke at Bobby’s Monkey Bar
Join the vibrant scene at Bobby's Monkey Bar in Old Town Key West for an unforgettable karaoke night. The spirited entertainer keeps the energy high,…
Riptide Riot at Irish Kevin’s Bar
Experience the electrifying energy of Riptide Riot at Irish Kevin’s Bar. This dynamic band brings non-stop live music, engaging the crowd with their lively performance…
Karaoke w/ Jorge ~ Rick’s Bar Downstairs Stage
Join DJ Jorge for an unforgettable night of karaoke at Rick's Bar Downstairs Stage. Known for his infectious energy and engaging personality, Jorge turns the…
Wednesday Filet Day at Mary Ellen’s
Every Wednesday at Mary Ellen's Bar in Old Town Key West, enjoy Filet Day alongside live entertainment that electrifies the neighborhood atmosphere. While savoring comfort…
Pierce August at Hog’s Breath Saloon
Pierce August captivates audiences at Hog's Breath Saloon with his dynamic performances and engaging stage presence. Known for his eclectic mix of genres, Pierce's music…
Dan Harvey Duo at Hog’s Breath Saloon
Experience the vibrant sounds of the Dan Harvey Duo at Hog's Breath Saloon in Key West. Renowned for their captivating performances, the duo brings a…
DJ Todd ~ Red Garter Saloon Stage
DJ Todd electrifies the Red Garter Saloon Stage at Rick's Entertainment Complex with an unforgettable mix of beats and rhythms. As the heart of Key…
DJ Duke ~ Rick’s Bar Upstairs Stage
Experience the electrifying sounds of DJ Duke at Rick's Bar Upstairs Stage, where his vibrant beats set the perfect mood for an unforgettable night. Known…
Marshall Morlock Band at General Horseplay
Experience the electrifying performances of the Marshall Morlock Band at General Horseplay, an iconic venue on Duval Street in Old Town Key West. Known for…
CRANK SINATRA~ Durty Harry’s Stage
Join Krank Sinatra on Durty Harry's Stage at Rick's Entertainment Complex in Key West's vibrant Old Town. Known for their electrifying performances, Krank Sinatra delivers…
Alex Anthony Band at Hog’s Breath Saloon
Experience the electrifying Alex Anthony Band live at Hog's Breath Saloon, where Alex's dynamic performance lights up Key West's favorite dive bar. Known for their…
Karaoke at Bobby’s Monkey Bar
Join the vibrant scene at Bobby's Monkey Bar in Old Town Key West for an unforgettable karaoke night. The spirited entertainer keeps the energy high,…
Kari Wolf at Irish Kevin’s Bar
Experience the electrifying performance of Kari Wolf at Irish Kevin’s Bar in Key West. Known for her dynamic stage presence and musical talent, Kari captivates…
Karaoke w/ Davis ~ Rick’s Bar Downstairs Stage
Join Davis for an unforgettable night of karaoke at Rick's Bar Downstairs Stage in Old Town Key West. Known for his dynamic energy and engaging…
Barrett Thomas at Hog’s Breath Saloon
Experience the dynamic performance of musician Barrett Thomas at Hog's Breath Saloon, where his captivating tunes energize the venue's lively atmosphere. Nestled in Key West's…
Dan Harvey Duo at Hog’s Breath Saloon
Experience the vibrant sounds of the Dan Harvey Duo at Hog's Breath Saloon. Known for their captivating performances, this talented musical duo creates an unforgettable…
DJ Marty ~ Red Garter Saloon Stage
Experience the electrifying beats of DJ Marty on the Red Garter Saloon Stage at Rick's Entertainment Complex in Key West. Known for his high-energy sets,…
Hot Girl Bummer at General Horseplay
Join the excitement at General Horseplay with Hot Girl Bummer, an electrifying entertainer known for her dynamic performances and infectious energy. Located in vibrant Old…
DJ Chaka ~ Rick’s Bar Upstairs Stage
Experience an electrifying night with DJ Chaka on the Rick's Bar Upstairs Stage. Known for spinning an eclectic mix of tunes that keep the crowd…
DURTBAGS~ Durty Harry’s Stage
Experience the electrifying energy of The Durtbags, Key West’s premier party rock band, at Durty Harry's Stage. Every Thursday through Sunday, they deliver unforgettable live…
Karaoke with Foss at RockHouse Live
Experience an unforgettable night of entertainment with Foss at RockHouse Live in Key West. Known for electrifying performances, Foss brings charisma and energy to the…
Alex Anthony Band at Hog’s Breath Saloon
Experience the electrifying Alex Anthony Band live at Hog's Breath Saloon, Key West. Known for their dynamic performances and captivating energy, Alex Anthony leads a…
Elle Haley and the Why Nots at General Horseplay
Elle Haley and the Why Nots captivate audiences at General Horseplay with their eclectic sound and magnetic stage presence. Known for their lively performances, this…
Karaoke at Bobby’s Monkey Bar
Join the vibrant scene at Bobby's Monkey Bar in Old Town Key West for an unforgettable karaoke night. The spirited entertainer keeps the energy high,…
Karaoke w/ Jason ~ Rick’s Bar Downstairs Stage
Join Jason for an unforgettable karaoke experience at Rick's Bar on the Downstairs Stage. Known for his engaging presence and charismatic hosting style, Jason turns…
Elle Haley at Hog’s Breath Saloon
Experience the captivating performance of musician Elle Haley at Hog's Breath Saloon, a vibrant venue in Key West's Mallory Square District. Elle fills the dive…
Dan Harvey Duo at Hog’s Breath Saloon
Experience the electrifying performance of the Dan Harvey Duo at Hog's Breath Saloon in Key West. Known for their captivating tunes and vibrant energy, the…
DJ Marty ~ Red Garter Saloon Stage
Experience the electrifying vibes of DJ Marty at the Red Garter Saloon Stage in Rick's Entertainment Complex. Known for his dynamic mixes and infectious energy,…
Karaoke at Two Friends Patio
Experience unforgettable evenings at Two Friends Patio with lively karaoke sessions hosted by charismatic entertainers. Sing your heart out on the open-air patio, soaking in…
DJ Duke ~ Rick’s Bar Upstairs Stage
Experience the electrifying beats of DJ Duke at Rick's Bar Upstairs Stage. Known for his dynamic sets and unparalleled energy, DJ Duke transforms the vibrant…
DURTBAGS ~ Durty Harry’s Stage
Catch Key West's ultimate party experience with The Durtbags at Durty Harry's Stage! This electrifying rock band performs live every Thursday through Sunday at Rick’s…
Alex Anthony Band at Hog’s Breath Saloon
Experience the vibrant sounds of the Alex Anthony Band at Hog's Breath Saloon. Known for electrifying performances, Alex Anthony captivates audiences with a unique blend…
David Warren Band at The Bull & Whistle Bar
Experience the electrifying performance of the David Warren Band at The Bull & Whistle Bar in Key West. Renowned for their dynamic stage presence and…
Karaoke at Bobby’s Monkey Bar
Join the vibrant scene at Bobby's Monkey Bar in Old Town Key West for an unforgettable karaoke night. The spirited entertainer keeps the energy high,…
Tequila Time Machine at General Horseplay
Experience the electrifying energy of Tequila Time Machine at General Horseplay, where this captivating band transports you through musical eras with their dynamic performances. Nestled…
Trumastr at Tiki House Key West
Experience the captivating performance of Trumastr at Tiki House Key West! Known for his dynamic presence and exceptional musical talent, Trumastr creates an unforgettable atmosphere…
Karaoke w/ Jason ~ Rick’s Bar Downstairs Stage
Join Jason for an unforgettable karaoke night at Rick's Bar Downstairs Stage. Known for his infectious energy and captivating charisma, Jason transforms the evening into…
Harley Ray at Hog’s Breath Saloon
Experience the electrifying performance of Harley Ray at Hog's Breath Saloon, where his dynamic musical talents light up the Key West night. Set against the…
Dan Harvey Duo at Hog’s Breath Saloon
Experience the captivating tunes of the Dan Harvey Duo at Hog's Breath Saloon, where live music fills the air in Key West's vibrant Mallory Square…
DJ Marty ~ Red Garter Saloon Stage
Experience the electrifying beats of DJ Marty at the Red Garter Saloon Stage in Rick's Entertainment Complex, Key West. Renowned for energizing mixes and captivating…
Zach Lovering at General Horseplay
Zach Lovering captivates audiences with his dynamic musical talent at General Horseplay in Key West. Known for his engaging performances, Zach's energetic style complements the…
DJ Chaka ~ Rick’s Bar Upstairs Stage
Experience an electrifying night with DJ Chaka at Rick's Bar Upstairs Stage. Renowned for energizing mixes and captivating beats, DJ Chaka transforms the dance floor…
DURTBAGS ~ Durty Harry’s Stage
Experience the ultimate Key West nightlife with The Durtbags at Durty Harry's Stage. Known as Key West’s biggest party rock band, they deliver electrifying performances…
Alex Anthony Band at Hog’s Breath Saloon
Experience the electrifying performance of the Alex Anthony Band at Hog's Breath Saloon. Known for their dynamic sound and engaging stage presence, the band brings…
DJ at Hinote at General Horseplay
At the heart of Duval Street, DJ Hinote electrifies General Horseplay with captivating beats and infectious energy. Renowned for creating unforgettable nights, Hinote masterfully mixes…
David Warren Band at The Bull & Whistle Bar
Experience an unforgettable evening with the David Warren Band at The Bull & Whistle Bar. Led by the talented David Bryce Warren, this lively band…
Karaoke at Bobby’s Monkey Bar
Join the vibrant scene at Bobby's Monkey Bar in Old Town Key West for an unforgettable karaoke night. The spirited entertainer keeps the energy high,…
The Tiki Bombs at Tiki House Key West
Experience the vibrant sounds of The Tiki Bombs at Tiki House Key West. Known for their energetic performances and infectious tropical tunes, this dynamic band…
Mike Stack & D-Lew at General Horseplay
Mike Stack & D-Lew bring their dynamic performances to the vibrant General Horseplay in Old Town Key West. Known for their engaging stage presence and…
Karaoke w/ Jason ~ Rick’s Bar Downstairs Stage
Join Jason for an unforgettable karaoke night at Rick's Bar Downstairs Stage in Key West. As the charismatic host, Jason brings unparalleled energy and entertainment,…
Aaron Blumer at Hog’s Breath Saloon
Experience an unforgettable evening with the talented musician Aaron Blumer at Hog's Breath Saloon in Key West's vibrant Mallory Square District. Known for his captivating…
Dan Harvey Duo at Hog’s Breath Saloon
Experience the captivating sounds of the Dan Harvey Duo at Hog's Breath Saloon, Key West. Dan Harvey, a talented musician, brings vibrant live music to…
DJ Marty ~ Red Garter Saloon Stage
Experience the electrifying beats of DJ Marty on the Red Garter Saloon Stage at Rick's Entertainment Complex. As the heart of Key West's nightlife scene,…
DJ Kori ~ Rick’s Bar Upstairs Stage
Experience the electrifying beats of DJ Kori at Rick's Bar Upstairs Stage in Key West's vibrant nightlife scene. DJ Kori crafts an unforgettable musical journey,…
DURTBAGS~ Durty Harry’s Stage
Experience the electrifying energy of The Durtbags, Key West’s ultimate party rock band, at Durty Harry’s Stage. Performing every Thursday through Sunday in the vibrant…
Alex Anthony Band at Hog’s Breath Saloon
Experience the captivating sounds of the Alex Anthony Band at Hog's Breath Saloon, where the talented group brings an electrifying blend of music to Key…
Karaoke at Bobby’s Monkey Bar
Join the vibrant scene at Bobby's Monkey Bar in Old Town Key West for an unforgettable karaoke night. The spirited entertainer keeps the energy high,…
Karaoke w/ Jason ~ Rick’s Bar Downstairs Stage
Join Jason for an unforgettable night of karaoke at Rick's Bar Downstairs Stage. Known for his infectious energy and dynamic hosting skills, Jason creates a…
Monday, February 16, 2026
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February 16, 2026 -Daytime event to test 40, Fireside
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February 16, 2026 -Daytime event to test 100, Stage A
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February 16, 2026 -Daytime event to test 102, Stage A
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February 16, 2026 -Fishmonster Max- Daily Party Boat Fishing
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February 16, 2026 -Yoga on the Beach – Ft Zachary Taylor
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February 16, 2026 -Aqua Yoga at Southernmost Beach Resort
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February 16, 2026 -Joe The Show at Sloppy Joe’s Bar
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February 16, 2026 -Bradd Shadduck at Irish Kevin’s Bar
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February 16, 2026 -Mojito Class by Key West Legal Rum Distillery – Min 4 people
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February 16, 2026 -Distillery Tour – Key West Legal Rum Distillery
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February 16, 2026 -Glass Bottom Boat – Key West’s Window to the sea
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February 16, 2026 -Glass Bottom Boat – Key West’s Window to the sea
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February 16, 2026 -Tim Hollohan at Sloppy Joe’s Bar
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February 16, 2026 -Jay Klein at Schooner Wharf Bar
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February 16, 2026 -Webb Dillard ~ Rick’s Bar Downstairs Stage
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February 16, 2026 -Rolando Rojas at Sunset Pier
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February 16, 2026 -Mic Smith at Hank’s Hair of the Dog Saloon
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February 16, 2026 -Kenny P at Tiki House Key West
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February 16, 2026 -Glass Bottom Boat – Key West’s Window to the sea
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February 16, 2026 -Glass Bottom Boat – Key West’s Window to the sea
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February 16, 2026 -Andrew Gordon at The Bull & Whistle Bar
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February 16, 2026 -Jeff Harris at Irish Kevin’s Bar
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February 16, 2026 -Just George ~ Rick’s Bar Downstairs Stage
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February 16, 2026 -Reef Snorkeling, Dolphin Watch Eco Tour & Sunset Cruise
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February 16, 2026 -Glass Bottom Boat – Key West’s Window to the sea
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February 16, 2026 -Glass Bottom Boat – Key West’s Window to the sea
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February 16, 2026 -Caribe of Key West at El Meson de Pepes on Mallory Square
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February 16, 2026 -World Famous 801 Girls- 5pm Show
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February 16, 2026 -Glow Hours on Hugh’s View
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February 16, 2026 -Jay Bangles at Tiki House Key West
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February 16, 2026 -Scott Morlock at Hank’s Hair of the Dog Saloon
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February 16, 2026 -Preacher Pete Presents at Sloppy Joe’s Bar
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February 16, 2026 -The 4 Amigos at Sunset Pier
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February 16, 2026 -NY Pauly at Irish Kevin’s Bar
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February 16, 2026 -Joe The Show at Schooner Wharf Bar
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February 16, 2026 -Charity Bingo at The Green Parrot
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February 16, 2026 -Charles Miller ~ Rick’s Bar Downstairs Stage
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February 16, 2026 -Jay Bangles at Tiki House Key West
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February 16, 2026 -Gerd Rube at The Bull & Whistle Bar
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February 16, 2026 -Bone Island Haunted Pub Crawl & Ghost Tour
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February 16, 2026 -Josh Kiser at Hank’s Hair of the Dog Saloon
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February 16, 2026LaurLea & Tripp Fabulous at Sloppy Joe’s Bar
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February 16, 2026Karaoke w/ Chris ~ Rick’s Bar Downstairs Stage
Fishmonster Max- Daily Party Boat Fishing
Fishmonster Max offers a thrilling daily party boat fishing experience in Key West, perfect for families and groups. With its stable twin hulls, the boat…
Yoga on the Beach – Ft Zachary Taylor
Join a unique yoga experience with renowned instructors at Yoga on the Beach at Fort Zachary Taylor. Set against the backdrop of Key West’s historic…
Aqua Yoga at Southernmost Beach Resort
Join an invigorating Aqua Yoga session at Southernmost Beach Resort, led by our expert instructor, who brings energy and tranquility to this unique waterside experience.…
Joe The Show at Sloppy Joe’s Bar
Experience the captivating performance of Joe The Show at Sloppy Joe's Bar, a Key West landmark since 1937. With his electrifying music and engaging presence,…
Bradd Shadduck at Irish Kevin’s Bar
Experience the captivating Bradd Shadduck at Irish Kevin’s Bar, where his dynamic performances enchant audiences in the lively heart of Key West. With engaging live…
Mojito Class by Key West Legal Rum Distillery – Min 4 people
There is a minimum of 4 people. Please contact mojitoclass@gmail.com to schedule. Please put how many people and date in the subject line. Join Key…
Distillery Tour – Key West Legal Rum Distillery
Experience an engaging distillery tour at Key West Legal Rum Distillery, featuring a skillful entertainer who brings the history and craft of rum making to…
Glass Bottom Boat – Key West’s Window to the sea
Experience the captivating Glass Bottom Boat tour in Key West, where our knowledgeable captain and crew offer an engaging eco-tour. Enjoy unparalleled views of North…
Tim Hollohan at Sloppy Joe’s Bar
Tim Hollohan captivates audiences at Sloppy Joe's Bar in Key West with his engaging stage presence and lively performances. Originally from Columbia, South Carolina, Tim…
Jay Klein at Schooner Wharf Bar
Experience the captivating tunes of musician Jay Klein at Schooner Wharf Bar in Key West. Known for his engaging performances, Jay brings vibrant live music…
Webb Dillard ~ Rick’s Bar Downstairs Stage
Experience the captivating performance of musician Webb Dillard on the Rick's Bar Downstairs Stage. Known for his enthralling melodies and dynamic presence, Webb brings a…
Rolando Rojas at Sunset Pier
Experience the captivating melodies of Rolando Rojas at Sunset Pier, where the musician's enchanting tunes harmonize perfectly with the breathtaking Key West sunset. Nestled at…
Mic Smith at Hank’s Hair of the Dog Saloon
Mic Smith captivates audiences at Hank's Hair of the Dog Saloon in Key West with his electrifying live performances. Known for his dynamic vocal range…
Kenny P at Tiki House Key West
Join the charismatic Kenny P for an unforgettable performance at Tiki House Key West. Known for his engaging stage presence and dynamic musical talent, Kenny…
Glass Bottom Boat – Key West’s Window to the sea
Experience the magic of Key West's marine life aboard the Glass Bottom Boat. While our knowledgeable captain and crew guide you on an informative eco-tour,…
Andrew Gordon at The Bull & Whistle Bar
Experience the captivating sounds of Andrew Gordon at The Bull & Whistle Bar in Key West. Known for his engaging performances, Andrew brings vibrant energy…
Jeff Harris at Irish Kevin’s Bar
Experience the dynamic performance of Jeff Harris at Irish Kevin’s Bar, where his lively music captivates the audience. Enjoy his engaging show that involves crowd…
Just George ~ Rick’s Bar Downstairs Stage
Experience the captivating sounds of Just George at Rick's Bar Downstairs Stage. This talented musician enchants audiences with his dynamic performances, creating an unforgettable atmosphere.…
Reef Snorkeling, Dolphin Watch Eco Tour & Sunset Cruise
Join us for a vibrant aquatic adventure in Key West with our Reef Snorkeling, Dolphin Watch Eco Tour, and Sunset Cruise. Our passionate and friendly…
Glass Bottom Boat – Key West’s Window to the sea
Experience an unforgettable journey with Glass Bottom Boat - Key West's Window to the Sea. With an engaging and knowledgeable captain and crew, embark on…
Caribe of Key West at El Meson de Pepes on Mallory Square
Caribe of Key West delivers an electrifying performance at El Meson de Pepe on Mallory Square, infusing the vibrant atmosphere with lively music. As you…
World Famous 801 Girls- 5pm Show
The World Famous 801 Girls captivate audiences with their dazzling performances at the lively 801 Bourbon Bar in Old Town Key West. Known for their…
Glow Hours on Hugh’s View
Experience captivating performances at Glow Hours on Hugh's View, perched atop the vibrant Studios of Key West. Set against the stunning backdrop of Key West's…
Jay Bangles at Tiki House Key West
Experience the vibrant sounds of Jay Bangles at Tiki House Key West. Known for his infectious energy and captivating performances, this talented musician brings a…
Scott Morlock at Hank’s Hair of the Dog Saloon
Scott Morlock captivates audiences at Hank's Hair of the Dog Saloon in Key West with his dynamic musical performances. Known for his engaging presence and…
Preacher Pete Presents at Sloppy Joe’s Bar
Experience the captivating performance of Key West legend Preacher Pete at Sloppy Joe's Bar. Known for his mesmerizing musical talent, Pete creates magical moments alongside…
The 4 Amigos at Sunset Pier
Experience the exhilarating performance of The 4 Amigos at Sunset Pier, where Duval Street meets the Gulf of Mexico. This vibrant band fills the air…
NY Pauly at Irish Kevin’s Bar
Catch NY Pauly at Irish Kevin’s Bar in Key West's vibrant Old Town for an unforgettable musical experience. Known for his energetic performances and engaging…
Joe The Show at Schooner Wharf Bar
Experience Joe The Show at Schooner Wharf Bar, where his dynamic performances captivate audiences with a lively mix of music. Set in Key West’s historic…
Charity Bingo at The Green Parrot
Experience Charity Bingo at The Green Parrot, where the main attraction is the vibrant live music that electrifies this historic Key West bar. With its…
Charles Miller ~ Rick’s Bar Downstairs Stage
Experience the captivating sounds of Charlie Miller at Rick's Bar Downstairs Stage in Key West. As a talented musician, Charlie brings a unique blend of…
Jay Bangles at Tiki House Key West
Experience the vibrant rhythms of Jay Bangles at Tiki House Key West. Known for captivating performances and infectious energy, Jay weaves a musical tapestry that…
Gerd Rube at The Bull & Whistle Bar
Experience the captivating performance of musician Gerd Rube at The Bull & Whistle Bar, a staple of Key West’s nightlife scene. Renowned for his dynamic…
Bone Island Haunted Pub Crawl & Ghost Tour
Join the Bone Island Haunted Pub Crawl & Ghost Tour for an enthralling evening led by a charismatic entertainer. With captivating narration, journey through America's…
Josh Kiser at Hank’s Hair of the Dog Saloon
Experience the vibrant sounds of Josh Kiser at Hank's Hair of the Dog Saloon in Key West. An exceptional musician, Kiser captivates audiences with his…
LaurLea & Tripp Fabulous at Sloppy Joe’s Bar
LaurLea & Tripp Fabulous bring their vibrant party rock vibes from Philadelphia to the iconic Sloppy Joe's Bar. With an energetic performance from 10:00 pm…
Karaoke w/ Chris ~ Rick’s Bar Downstairs Stage
Join Chris for a lively karaoke night at Rick's Bar Downstairs Stage. Renowned for energizing performances, Chris turns every song into an unforgettable experience. Enjoy…
Tuesday, February 17, 2026
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February 17, 2026 -Ambitious Morning Runners
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February 17, 2026 -Daytime event to test 101, Stage A
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February 17, 2026 -Fishmonster Max- Daily Party Boat Fishing
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February 17, 2026 -Yoga on the Beach – Ft Zachary Taylor
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February 17, 2026 -Prime of Life Yoga with Monica Haskell
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February 17, 2026 -Nina Newton at Sloppy Joe’s Bar
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February 17, 2026 -Bradd Shadduck at Irish Kevin’s Bar
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February 17, 2026 -Distillery Tour – Key West Legal Rum Distillery
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February 17, 2026 -Mojito Class by Key West Legal Rum Distillery – Min 4 people
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February 17, 2026 -Brian Roberts at Sloppy Joe’s Bar
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February 17, 2026 -Oren Polak at Schooner Wharf Bar
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February 17, 2026 -Shanty Hounds ~Rick’s Bar Downstairs Stage
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February 17, 2026 -Billy Ruegger at Sunset Pier
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February 17, 2026 -Tony Baltimore at Hank’s Hair of the Dog Saloon
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February 17, 2026 -Joe The Show at Tiki House Key West
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February 17, 2026 -Jessie Cotton Stone at The Bull & Whistle Bar
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February 17, 2026 -Irish Kevin at Irish Kevin’s Bar
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February 17, 2026 -Jesse Lee ~Rick’s Bar Downstairs Stage
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February 17, 2026 -Reef Snorkeling, Dolphin Watch Eco Tour & Sunset Cruise
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February 17, 2026 -Caribe of Key West at El Meson de Pepes on Mallory Square
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February 17, 2026 -World Famous 801 Girls- 5pm Show
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February 17, 2026 -Glow Hours on Hugh’s View
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February 17, 2026 -Jay Klein at Hank’s Hair of the Dog Saloon
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February 17, 2026 -Burning Bridges at Sloppy Joe’s Bar
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February 17, 2026 -CC and The Sunsetters at Sunset Pier
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February 17, 2026 -NY Pauly at Irish Kevin’s Bar
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February 17, 2026 -Gary Hempsey at Schooner Wharf Bar
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February 17, 2026 -Ben Harrison at Key West Theater
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February 17, 2026 -Joe the Show ~ Rick’s Bar Downstairs Stage
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February 17, 2026 -Aaron Hudgins at Tiki House Key West
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February 17, 2026 -Marshall Morlock at The Bull & Whistle Bar
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February 17, 2026 -iWITNESS True Crime Walking Tour
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February 17, 2026 -iWITNESS True Crime Walking Tour
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February 17, 2026 -The Original Key West Pub Crawl
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February 17, 2026 -Bone Island Haunted Pub Crawl & Ghost Tour
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February 17, 2026 -Barrett Thomas at Hank’s Hair of the Dog Saloon
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February 17, 2026LaurLea & Tripp Fabulous at Sloppy Joe’s Bar
Ambitious Morning Runners
Join the Ambitious Morning Runners at White Street Pier in Key West for an invigorating start to your day. While there isn't a specific entertainer,…
Fishmonster Max- Daily Party Boat Fishing
Join Fishmonster Max for an unforgettable daily party boat fishing adventure in Key West, where entertainment meets the thrill of fishing. Whether it's a family…
Yoga on the Beach – Ft Zachary Taylor
Join a unique yoga experience with renowned instructors at Yoga on the Beach at Fort Zachary Taylor. Set against the backdrop of Key West’s historic…
Prime of Life Yoga with Monica Haskell
Join Monica Haskell for Prime of Life Yoga, a rejuvenating experience amidst the serene beauty of the Key West Tropical Forest & Botanical Garden. Known…
Nina Newton at Sloppy Joe’s Bar
Nina Newton graces Sloppy Joe's Bar with her soulful voice and R&B flair, captivating music enthusiasts with every note. A celebrated Key West legend, she…
Bradd Shadduck at Irish Kevin’s Bar
Bradd Shadduck electrifies the crowd at Irish Kevin’s Bar with his dynamic live performances. A talented musician, he masterfully engages the audience, transforming the lively…
Distillery Tour – Key West Legal Rum Distillery
Experience an engaging distillery tour at Key West Legal Rum Distillery, featuring a skillful entertainer who brings the history and craft of rum making to…
Mojito Class by Key West Legal Rum Distillery – Min 4 people
There is a minimum of 4 people. Please contact mojitoclass@gmail.com to schedule. Please put how many people and date in the subject line. Join Key…
Brian Roberts at Sloppy Joe’s Bar
Brian Roberts captivates audiences with his electrifying performances at the iconic Sloppy Joe's Bar in Key West. Known for his dynamic musical prowess, Roberts brings…
Oren Polak at Schooner Wharf Bar
Experience the captivating performance of Oren Polak at Schooner Wharf Bar, Key West's iconic waterfront venue. Known for its laid-back vibe and stunning seaport views,…
Shanty Hounds ~Rick’s Bar Downstairs Stage
Experience the vibrant sounds of the Shanty Hounds at Rick's Bar Downstairs Stage in Key West. This talented band brings an infectious energy to the…
Billy Ruegger at Sunset Pier
Experience the captivating performance of musician Billy Ruegger at Sunset Pier in Key West. With the stunning backdrop of the Gulf of Mexico, Billy’s soulful…
Tony Baltimore at Hank’s Hair of the Dog Saloon
Tony Baltimore brings his captivating musical talent to Hank's Hair of the Dog Saloon in Key West. Known for his engaging performances, Tony's music is…
Joe The Show at Tiki House Key West
Experience an unforgettable evening with Joe The Show at Tiki House Key West. This talented musician delivers captivating performances, blending dynamic music with engaging stage…
Jessie Cotton Stone at The Bull & Whistle Bar
Experience the captivating performance of Jessie Cotton Stone at The Bull & Whistle Bar, a lively venue in Key West’s vibrant Old Town. Known for…
Irish Kevin at Irish Kevin’s Bar
Irish Kevin captivates audiences at Irish Kevin’s Bar with his dynamic live music and engaging performances. Known for creating an electric atmosphere, he encourages crowd…
Jesse Lee ~Rick’s Bar Downstairs Stage
Catch the electrifying performance of Jesse Lee Jr at Rick's Bar Downstairs Stage, located within Key West's renowned Rick's Entertainment Complex. As a captivating musician,…
Reef Snorkeling, Dolphin Watch Eco Tour & Sunset Cruise
Join an exhilarating aquatic adventure with the Reef Snorkeling, Dolphin Watch Eco Tour & Sunset Cruise. Led by our passionate and expert staff, enjoy thrilling…
Caribe of Key West at El Meson de Pepes on Mallory Square
Caribe of Key West delivers an electrifying performance at El Meson de Pepe on Mallory Square, infusing the vibrant atmosphere with lively music. As you…
World Famous 801 Girls- 5pm Show
The World Famous 801 Girls captivate audiences with their dazzling performances at the lively 801 Bourbon Bar in Old Town Key West. Known for their…
Glow Hours on Hugh’s View
Experience captivating performances at Glow Hours on Hugh's View, perched atop the vibrant Studios of Key West. Set against the stunning backdrop of Key West's…
Jay Klein at Hank’s Hair of the Dog Saloon
Experience the captivating performance of musician Jay Klein at Hank's Hair of the Dog Saloon in Key West. Renowned for his dynamic live shows, Jay…
Burning Bridges at Sloppy Joe’s Bar
Experience the electrifying performance of Burning Bridges at Sloppy Joe's Bar, a historic Key West landmark known for its vibrant atmosphere and live entertainment. This…
CC and The Sunsetters at Sunset Pier
Experience the vibrant sounds of CC and The Sunsetters at Sunset Pier, where their lively performances captivate audiences against the stunning backdrop of the Key…
NY Pauly at Irish Kevin’s Bar
NY Pauly, a charismatic musician, enthralls audiences at Irish Kevin’s Bar in Key West with his lively performances and engaging style. Known for his dynamic…
Gary Hempsey at Schooner Wharf Bar
Gary Hempsey delivers captivating live performances at the Schooner Wharf Bar, a cherished Key West hotspot. Renowned for his musical prowess, Gary enchants audiences with…
Ben Harrison at Key West Theater
Experience the captivating talent of musician Ben Harrison at the Key West Theater's Backstage Listening Room. Known for his engaging performances, Harrison brings his unique…
Joe the Show ~ Rick’s Bar Downstairs Stage
Experience the unmatched talent of Joe the Show at Rick's Bar Downstairs Stage. Known for captivating performances, Joe brings energy and charisma to the heart…
Aaron Hudgins at Tiki House Key West
Experience the captivating performance of musician Aaron Hudgins at Tiki House Key West. Known for his dynamic stage presence and soulful melodies, Hudgins delivers an…
Marshall Morlock at The Bull & Whistle Bar
Marshall Morlock captivates audiences at The Bull & Whistle Bar, nestled in Key West's vibrant Old Town. Known for his engaging performances, Morlock delivers a…
iWITNESS True Crime Walking Tour
Join the iWITNESS True Crime Walking Tour and embark on a thrilling journey through Key West's most notorious crime scenes. Led by an engaging expert…
iWITNESS True Crime Walking Tour
Join the iWITNESS True Crime Walking Tour and embark on a thrilling journey through Key West's most notorious crime scenes. Led by an engaging expert…
The Original Key West Pub Crawl
Join The Original Key West Pub Crawl for a lively 2.5-hour adventure spotlighted by entertaining guides who infuse humor and energy into the experience. Enjoy…
Bone Island Haunted Pub Crawl & Ghost Tour
Join the Bone Island Haunted Pub Crawl & Ghost Tour for an enthralling evening led by a charismatic entertainer. With captivating narration, journey through America's…
Barrett Thomas at Hank’s Hair of the Dog Saloon
Experience the captivating performance of Barrett Thomas at Hank's Hair of the Dog Saloon. Known for his engaging stage presence and musical prowess, Barrett delivers…
LaurLea & Tripp Fabulous at Sloppy Joe’s Bar
LaurLea & Tripp Fabulous bring the party rock vibes from Philadelphia to Sloppy Joe's Bar. With their dynamic performances and energetic beats, they captivate audiences…
Wednesday, February 18, 2026
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February 18, 2026 -Daytime event to test 103, Stage A
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February 18, 2026 -Fishmonster Max- Daily Party Boat Fishing
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February 18, 2026 -Yoga on the Beach – Ft Zachary Taylor
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February 18, 2026 -Aqua Yoga at Southernmost Beach Resort
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February 18, 2026 -Izzy Zaidman at Sloppy Joe’s Bar
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February 18, 2026 -Oren Polak at Irish Kevin’s Bar
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February 18, 2026 -Distillery Tour – Key West Legal Rum Distillery
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February 18, 2026 -Mojito Class by Key West Legal Rum Distillery – Min 4 people
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February 18, 2026 -Glass Bottom Boat Cruise – Key West’s Window to the Sea
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February 18, 2026 -Brian Roberts at Sloppy Joe’s Bar
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February 18, 2026 -Tony Baltimore at Schooner Wharf Bar
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February 18, 2026 -Michael Corleto ~ Rick’s Bar Downstairs Stage
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February 18, 2026 -Claire Finley at Sunset Pier
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February 18, 2026 -Shastina Chiles at Hank’s Hair of the Dog Saloon
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February 18, 2026 -Jesse James Russell at Tiki House Key West
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February 18, 2026 -Glass Bottom Boat Cruise – Key West’s Window to the Sea
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February 18, 2026 -Mac Calhoun at The Bull & Whistle Bar
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February 18, 2026 -Bradd Shadduck at Irish Kevin’s Bar
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February 18, 2026 -Harley Ray ~ Rick’s Bar Downstairs Stage
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February 18, 2026 -Reef Snorkeling, Dolphin Watch Eco Tour & Sunset Cruise
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February 18, 2026 -Glass Bottom Boat Cruise – Key West’s Window to the Sea
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February 18, 2026 -Caribe of Key West at El Meson de Pepes on Mallory Square
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February 18, 2026 -World Famous 801 Girls- 5pm Show
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February 18, 2026 -Jay Bangles at Tiki House Key West
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February 18, 2026 -Cliff Cody at Hank’s Hair of the Dog Saloon
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February 18, 2026 -Victoria Leigh at Sloppy Joe’s Bar
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February 18, 2026 -Jerica Rockabilly Quartet at Sunset Pier
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February 18, 2026 -Irish Kevin at Irish Kevin’s Bar
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February 18, 2026 -Jesse James at Schooner Wharf Bar
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February 18, 2026 -Magic Of Frank Everhart at Schooner Wharf Bar
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February 18, 2026 -Andrew B. ~ Rick’s Bar Downstairs Stage
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February 18, 2026 -Jay Bangles at Tiki House Key West
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February 18, 2026 -Yachtley Crew at Key West Theater
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February 18, 2026 -Kristen McNamara at The Bull & Whistle Bar
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February 18, 2026 -Bone Island Haunted Pub Crawl & Ghost Tour
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February 18, 2026 -Andy Sands at Hank’s Hair of the Dog Saloon
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February 18, 2026Naked Karate Girls at Sloppy Joe’s Bar
Fishmonster Max- Daily Party Boat Fishing
Fishmonster Max offers a thrilling daily party boat fishing experience in Key West, perfect for families and groups. With its stable twin hulls, the boat…
Yoga on the Beach – Ft Zachary Taylor
Join a unique yoga experience with renowned instructors at Yoga on the Beach at Fort Zachary Taylor. Set against the backdrop of Key West’s historic…
Aqua Yoga at Southernmost Beach Resort
Join an invigorating Aqua Yoga session at Southernmost Beach Resort, led by our expert instructor, who brings energy and tranquility to this unique waterside experience.…
Izzy Zaidman at Sloppy Joe’s Bar
Izzy Zaidman, a talented musician, brings the vibrant sound of American Roots to Sloppy Joe's Bar in Key West. With his Steel Resonator guitar, Izzy…
Oren Polak at Irish Kevin’s Bar
Oren Polak brings his dynamic musical talent to Irish Kevin's Bar, captivating audiences with his engaging performances. Set in the heart of Key West's lively…
Distillery Tour – Key West Legal Rum Distillery
Experience an engaging distillery tour at Key West Legal Rum Distillery, featuring a skillful entertainer who brings the history and craft of rum making to…
Mojito Class by Key West Legal Rum Distillery – Min 4 people
There is a minimum of 4 people. Please contact mojitoclass@gmail.com to schedule. Please put how many people and date in the subject line. Join Key…
Glass Bottom Boat Cruise – Key West’s Window to the Sea
Experience the captivating Glass Bottom Boat tour in Key West, where our knowledgeable captain and crew offer an engaging eco-tour. Enjoy unparalleled views of North…
Brian Roberts at Sloppy Joe’s Bar
Experience the captivating music of Brian Roberts at Sloppy Joe's Bar in Key West. With his dynamic performance that seamlessly blends genres, Roberts brings the…
Tony Baltimore at Schooner Wharf Bar
Tony Baltimore, a talented musician, brings his captivating sound to the historic Schooner Wharf Bar in Key West. Known for his engaging performances, Tony's music…
Michael Corleto ~ Rick’s Bar Downstairs Stage
Experience the electrifying performance of Michael Corleto at Rick's Bar Downstairs Stage. Known for his captivating presence and dynamic musical talent, Michael promises an unforgettable…
Claire Finley at Sunset Pier
Claire Finley captivates audiences at Sunset Pier with her soulful melodies and dynamic stage presence. Her performances, set against the backdrop of Key West's breathtaking…
Shastina Chiles at Hank’s Hair of the Dog Saloon
Experience the captivating performance of musician Shastina Chiles at Hank's Hair of the Dog Saloon in Key West. Known for her vibrant stage presence and…
Jesse James Russell at Tiki House Key West
Jesse James Russell captivates audiences at Tiki House Key West with his engaging performances and dynamic stage presence. Known for his versatile musical talent and…
Glass Bottom Boat Cruise – Key West’s Window to the Sea
Experience the magic of Key West's marine life aboard the Glass Bottom Boat. While our knowledgeable captain and crew guide you on an informative eco-tour,…
Mac Calhoun at The Bull & Whistle Bar
Experience the musical prowess of Mac Calhoun at The Bull & Whistle Bar, a vibrant venue in Key West’s Old Town. Renowned for his dynamic…
Bradd Shadduck at Irish Kevin’s Bar
Bradd Shadduck brings his dynamic musical talent to Irish Kevin’s Bar in Key West’s vibrant Old Town. Renowned for his engaging performances, Bradd captivates audiences…
Harley Ray ~ Rick’s Bar Downstairs Stage
Experience Harley Ray's captivating live performance at Rick's Bar Downstairs Stage in Old Town Key West. Known for their engaging musical talent, Harley Ray creates…
Reef Snorkeling, Dolphin Watch Eco Tour & Sunset Cruise
Join us for a vibrant aquatic adventure in Key West with our Reef Snorkeling, Dolphin Watch Eco Tour, and Sunset Cruise. Our passionate and friendly…
Glass Bottom Boat Cruise – Key West’s Window to the Sea
Experience an unforgettable journey with Glass Bottom Boat - Key West's Window to the Sea. With an engaging and knowledgeable captain and crew, embark on…
Caribe of Key West at El Meson de Pepes on Mallory Square
Caribe of Key West delivers an electrifying performance at El Meson de Pepe on Mallory Square, infusing the vibrant atmosphere with lively music. As you…
World Famous 801 Girls- 5pm Show
The World Famous 801 Girls captivate audiences with their dazzling performances at the lively 801 Bourbon Bar in Old Town Key West. Known for their…
Jay Bangles at Tiki House Key West
Experience an unforgettable evening with Jay Bangles at Tiki House Key West. Known for his vibrant musical talent, Jay captivates audiences with his unique blend…
Cliff Cody at Hank’s Hair of the Dog Saloon
Experience the soulful and captivating performance of musician Cliff Cody at Hank's Hair of the Dog Saloon. Known for his engaging stage presence and powerful…
Victoria Leigh at Sloppy Joe’s Bar
Victoria Leigh, a dynamic singer, guitarist, and loop artist from the Florida Keys, electrifies audiences with her high-energy performances at Sloppy Joe's Bar. Known for…
Jerica Rockabilly Quartet at Sunset Pier
Experience the electrifying Jerico Rockabilly Quartet at Sunset Pier, where their energetic tunes and dynamic performances captivate audiences against the stunning Key West sunset. Nestled…
Irish Kevin at Irish Kevin’s Bar
Experience the vibrant atmosphere at Irish Kevin’s Bar with the charismatic entertainer, Irish Kevin, as he captivates the crowd with his lively performances and engaging…
Jesse James at Schooner Wharf Bar
Jesse James captivates audiences at the Schooner Wharf Bar with his dynamic performances set against the backdrop of Key West's picturesque seaport. Known for his…
Magic Of Frank Everhart at Schooner Wharf Bar
Experience the captivating Magic of Frank Everhart at Schooner Wharf Bar, where his mesmerizing illusions and charismatic presence enchant audiences in a laid-back, open-air waterfront…
Andrew B. ~ Rick’s Bar Downstairs Stage
Experience the captivating performance of Andrew B., a talented musician, on the Downstairs Stage at Rick's Bar. Nestled in Key West's vibrant entertainment hub, Rick's…
Jay Bangles at Tiki House Key West
Experience the vibrant sounds of Jay Bangles at Tiki House Key West. This dynamic musician captivates audiences with an electrifying performance, blending soulful tunes with…
Yachtley Crew at Key West Theater
Prepare for an unforgettable night with Yachtley Crew at the Key West Theater. Known as The Titans of Soft Rock, Yachtley Crew delivers captivating renditions…
Kristen McNamara at The Bull & Whistle Bar
Experience the mesmerizing talent of Kristen McNamara at The Bull & Whistle Bar. Known for her captivating performances, Kristen brings a unique blend of soulful…
Bone Island Haunted Pub Crawl & Ghost Tour
Join the Bone Island Haunted Pub Crawl & Ghost Tour for an enthralling evening led by a charismatic entertainer. With captivating narration, journey through America's…
Andy Sands at Hank’s Hair of the Dog Saloon
Experience the captivating performance of musician Andy Sands at Hank's Hair of the Dog Saloon in Key West. Known for his engaging stage presence and…
Naked Karate Girls at Sloppy Joe’s Bar
Experience the electrifying energy of the Naked Karate Girls, the ultimate party band hailing from Cincinnati. Known as The Best Band in the Galaxy, their…
Thursday, February 19, 2026
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February 19, 2026 -Ambitious Morning Runners
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February 19, 2026 -Daytime event to test 104, Stage A
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February 19, 2026 -Daytime event to test 106, Stage B
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February 19, 2026 -Daytime event to test 107, Stage C
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February 19, 2026 -Daytime event to test 108, Stage D
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February 19, 2026 -Fishmonster Max- Daily Party Boat Fishing
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February 19, 2026 -Yoga on the Beach – Ft Zachary Taylor
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February 19, 2026 -Prime of Life Yoga with Monica Haskell
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February 19, 2026 -Victoria Leigh at Sloppy Joe’s Bar
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February 19, 2026 -Trenton Chandler ~ Rick’s DownStairs Stage
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February 19, 2026 -Mylo O’Maolain at Irish Kevin’s Bar
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February 19, 2026 -Distillery Tour – Key West Legal Rum Distillery
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February 19, 2026 -Mojito Class by Key West Legal Rum Distillery – Min 4 people
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February 19, 2026 -Glass Bottom Boat Cruise – Key West’s Window to the Sea
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February 19, 2026 -Ross Brown at Schooner Wharf Bar
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February 19, 2026 -Sid The Bayou Kid at Sloppy Joe’s Bar
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February 19, 2026 -Truman Waterfront Farmers Market
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February 19, 2026 -Marjory Lee at Sunset Pier
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February 19, 2026 -Tony Baltimore at Hank’s Hair of the Dog Saloon
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February 19, 2026 -Jon Hollywood at Tiki House Key West
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February 19, 2026 -David Warren at The Bull & Whistle Bar
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February 19, 2026 -Irish Kevin at Irish Kevin’s Bar
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February 19, 2026 -Jeff Harris ~ Rick’s Bar Downstairs Stage
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February 19, 2026 -Reef Snorkeling, Dolphin Watch Eco Tour & Sunset Cruise
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February 19, 2026 -Glass Bottom Boat Cruise – Key West’s Window to the Sea
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February 19, 2026 -Sunset Celebration at Mallory Square
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February 19, 2026 -Caribe of Key West at El Meson de Pepes on Mallory Square
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February 19, 2026 -World Famous 801 Girls- 5pm Show
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February 19, 2026 -Elle Haley at Hank’s Hair of the Dog Saloon
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February 19, 2026 -Pete & Larry Sloppy 2nds at Sloppy Joe’s Bar
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February 19, 2026 -Reggae Lou and The Kind Buda at Sunset Pier
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February 19, 2026 -Filming Sit with Kit Podcast Episodes
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February 19, 2026 -Bria Ansara at Berlin’s Cocktail Bar
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February 19, 2026 -Nick Brownell at Schooner Wharf Bar
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February 19, 2026 -Andy’s Cabana Open Mic No Mic Night
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February 19, 2026 -Catch The Mania Trivia at Brady’s Pub
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February 19, 2026 -Magic Of Frank Everhart at Schooner Wharf Bar
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February 19, 2026 -Joe the Show ~ Rick’s Bar Downstairs Stage
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February 19, 2026 -Marty Stuart And His Fabulous Superlatives at Key West Theater
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February 19, 2026 -Sandra Lee at The Bull & Whistle Bar
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February 19, 2026 -The Tiki Bombs at Tiki House Key West
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February 19, 2026 -Barrett Thomas at Hank’s Hair of the Dog Saloon
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February 19, 2026Naked Karate Girls at Sloppy Joe’s Bar
Ambitious Morning Runners
Join the Ambitious Morning Runners at White Street Pier in Key West for an invigorating start to your day. While there isn't a specific entertainer,…
Fishmonster Max- Daily Party Boat Fishing
Join Fishmonster Max for an unforgettable daily party boat fishing adventure in Key West, where entertainment meets the thrill of fishing. Whether it's a family…
Yoga on the Beach – Ft Zachary Taylor
Join a unique yoga experience with renowned instructors at Yoga on the Beach at Fort Zachary Taylor. Set against the backdrop of Key West’s historic…
Prime of Life Yoga with Monica Haskell
Join Monica Haskell for Prime of Life Yoga, a rejuvenating experience amidst the serene beauty of the Key West Tropical Forest & Botanical Garden. Known…
Victoria Leigh at Sloppy Joe’s Bar
Victoria Leigh, a dynamic Florida Keys singer, guitarist, and loop artist, electrifies audiences at Sloppy Joe's Bar. Known for her energetic performances and creative mashups,…
Trenton Chandler ~ Rick’s DownStairs Stage
Catch the electrifying performance of Trenton Chandler at Rick's DownStairs Stage in Key West. A talented country musician from Shallowater, Texas, Trenton draws inspiration from…
Mylo O’Maolain at Irish Kevin’s Bar
Catch Mylo O'Maolain live at Irish Kevin's Bar in Key West's vibrant Old Town. Experience his dynamic musical performances, engaging the crowd with every note.…
Distillery Tour – Key West Legal Rum Distillery
Experience an engaging distillery tour at Key West Legal Rum Distillery, featuring a skillful entertainer who brings the history and craft of rum making to…
Mojito Class by Key West Legal Rum Distillery – Min 4 people
There is a minimum of 4 people. Please contact mojitoclass@gmail.com to schedule. Please put how many people and date in the subject line. Join Key…
Glass Bottom Boat Cruise – Key West’s Window to the Sea
Experience the captivating Glass Bottom Boat tour in Key West, where our knowledgeable captain and crew offer an engaging eco-tour. Enjoy unparalleled views of North…
Ross Brown at Schooner Wharf Bar
Experience the captivating sounds of Ross Brown at Schooner Wharf Bar, Key West. This talented musician brings vibrant energy to the historic, open-air setting, enhancing…
Sid The Bayou Kid at Sloppy Joe’s Bar
Sid The Bayou Kid, a charismatic musician from Thibodaux, LA, captivates audiences with his swamp-infused sound. With over 30 years of experience, Sid brings his…
Truman Waterfront Farmers Market
Enjoy the vibrant atmosphere at Truman Waterfront Farmers Market, where local entertainers set the mood with captivating performances. Every Thursday from 2 to 7 pm,…
Marjory Lee at Sunset Pier
Experience the captivating sounds of musician Marjory Lee at Sunset Pier, where her enchanting performances complement the vibrant ambiance of Key West's waterfront. Nestled where…
Tony Baltimore at Hank’s Hair of the Dog Saloon
Tony Baltimore brings his captivating musical talent to Hank's Hair of the Dog Saloon in Key West. Known for his dynamic performances, Tony enchants audiences…
Jon Hollywood at Tiki House Key West
Join the charismatic Jon Hollywood at Tiki House Key West for an unforgettable evening of entertainment. Known for his captivating performances and energetic stage presence,…
David Warren at The Bull & Whistle Bar
Experience the captivating performance of David Warren at The Bull & Whistle Bar in Key West. Known for his dynamic stage presence and soulful tunes,…
Irish Kevin at Irish Kevin’s Bar
Experience the charismatic performances of Irish Kevin at Irish Kevin’s Bar in Key West's Old Town. Known for his engaging live music and dynamic crowd…
Jeff Harris ~ Rick’s Bar Downstairs Stage
Experience the captivating talent of musician Jeff Harris at Rick's Bar Downstairs Stage. Located in vibrant Old Town Key West, this venue is part of…
Reef Snorkeling, Dolphin Watch Eco Tour & Sunset Cruise
Join an exhilarating aquatic adventure with the Reef Snorkeling, Dolphin Watch Eco Tour & Sunset Cruise. Led by our passionate and expert staff, enjoy thrilling…
Glass Bottom Boat Cruise – Key West’s Window to the Sea
Experience an unforgettable journey with Glass Bottom Boat - Key West's Window to the Sea. With an engaging and knowledgeable captain and crew, embark on…
Sunset Celebration at Mallory Square
The Sunset Celebration at Mallory Square in Key West is a must-see event. Renowned street performers captivate audiences with their vibrant talents, creating an unforgettable…
Caribe of Key West at El Meson de Pepes on Mallory Square
Caribe of Key West delivers an electrifying performance at El Meson de Pepe on Mallory Square, infusing the vibrant atmosphere with lively music. As you…
World Famous 801 Girls- 5pm Show
The World Famous 801 Girls captivate audiences with their dazzling performances at the lively 801 Bourbon Bar in Old Town Key West. Known for their…
Elle Haley at Hank’s Hair of the Dog Saloon
Elle Haley captivates audiences at Hank's Hair of the Dog Saloon with her mesmerizing musical performances. Known for her dynamic vocals and engaging stage presence,…
Pete & Larry Sloppy 2nds at Sloppy Joe’s Bar
Catch the dynamic duo Pete & Larry, better known as Sloppy 2nds, at the iconic Sloppy Joe's Bar. With their infectious humor and lively performances,…
Reggae Lou and The Kind Buda at Sunset Pier
Experience the captivating rhythms of Reggae Lou and The Kind Budz at Sunset Pier, Key West. This dynamic band infuses the air with reggae vibes,…
Filming Sit with Kit Podcast Episodes
Join charismatic host Kit in filming Sit with Kit podcast episodes at Angelina's Pizzeria in Key West. Known for its vibrant energy and engaging conversations,…
Bria Ansara at Berlin’s Cocktail Bar
Immerse yourself in an unforgettable evening with Bria Ansara at Berlin's Cocktail Bar. Nestled in Key West's A&B Lobster House, this hidden gem offers a…
Nick Brownell at Schooner Wharf Bar
Nick Brownell brings his musical talents to the iconic Schooner Wharf Bar, a beloved Key West venue known for its relaxed atmosphere and stunning dockside…
Andy’s Cabana Open Mic No Mic Night
At Andy's Cabana Open Mic No Mic Night, the real star is the performer who captivates the audience with raw, acoustic talent. In the heart…
Catch The Mania Trivia at Brady’s Pub
Join us at Brady's Pub for Catch The Mania Trivia, hosted by an enigmatic entertainer who promises a night of fun and excitement. Dive into…
Magic Of Frank Everhart at Schooner Wharf Bar
Experience the enchanting Magic of Frank Everhart at Schooner Wharf Bar in Key West's Seaport. A master magician, Everhart captivates audiences with mesmerizing illusions and…
Joe the Show ~ Rick’s Bar Downstairs Stage
Experience the electrifying performance of Joe the Show at Rick's Bar Downstairs Stage in the heart of Key West. This dynamic musician captivates audiences with…
Marty Stuart And His Fabulous Superlatives at Key West Theater
Experience the legendary Marty Stuart and His Fabulous Superlatives as they bring their electrifying performance to the historic Key West Theater. Known for his mastery…
Sandra Lee at The Bull & Whistle Bar
Sandra Lee captivates audiences at The Bull & Whistle Bar in Key West with her electrifying performances. Known for her dynamic musical talent, Sandra brings…
The Tiki Bombs at Tiki House Key West
Experience an unforgettable night with The Tiki Bombs at the Tiki House Key West. This electrifying band brings a vibrant, energetic performance, delivering explosive sounds…
Barrett Thomas at Hank’s Hair of the Dog Saloon
Experience the captivating sounds of Barrett Thomas at Hank's Hair of the Dog Saloon in Key West. Known for his engaging performances, Barrett brings lively…
Naked Karate Girls at Sloppy Joe’s Bar
The Naked Karate Girls, hailed as the best band in the galaxy, bring their high-energy performance to Sloppy Joe's Bar from 10:00 pm to 2:00…
Friday, February 20, 2026
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February 20, 2026 -Daytime event to test 105, Stage A
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February 20, 2026 -Daytime event to test 109, Stage B
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February 20, 2026 -Daytime event to test 110, Stage C
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February 20, 2026 -Daytime event to test 111, Stage D
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February 20, 2026 -Yoga on the Beach – Smather’s Beach
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February 20, 2026 -Fishmonster Max- Daily Party Boat Fishing
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February 20, 2026 -Yoga on the Beach – Ft Zachary Taylor
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February 20, 2026 -Rolando Rojas at Sloppy Joe’s Bar
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February 20, 2026 -Story Time at the Key West Library
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February 20, 2026 -Distillery Tour – Key West Legal Rum Distillery
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February 20, 2026 -Mojito Class by Key West Legal Rum Distillery – Min 4 people
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February 20, 2026 -Glass Bottom Boat Cruise – Key West’s Window to the Sea
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February 20, 2026 -Tim Hollohan at Sloppy Joe’s Bar
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February 20, 2026 -Tony Baltimore at Schooner Wharf Bar
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February 20, 2026 -Wynn Tayor ~ Rick’s Bar Downstairs Stage
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February 20, 2026 -Mike Stack & D-Lew at Tiki House Key West
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February 20, 2026 -Jockey Jord at Sunset Pier
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February 20, 2026 -Pat Guadano and Friends at Hank’s Hair of the Dog Saloon
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February 20, 2026 -Glass Bottom Boat Cruise – Key West’s Window to the Sea
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February 20, 2026 -Jessie Cotton Stone at The Bull & Whistle Bar
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February 20, 2026 -Fishmonster Max- Daily Party Boat Fishing
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February 20, 2026 -Reef Snorkeling, Dolphin Watch Eco Tour & Sunset Cruise
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February 20, 2026 -Joe the Show ~ Rick’s Bar Downstairs Stage
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February 20, 2026 -Glass Bottom Boat Cruise – Key West’s Window to the Sea
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February 20, 2026 -Sunset Celebration at Mallory Square
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February 20, 2026 -Rochi and Prince at Hank’s Hair of the Dog Saloon
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February 20, 2026 -Pete & Larry Sloppy 2nds at Sloppy Joe’s Bar
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February 20, 2026 -Snacks and Five at Sunset Pier
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February 20, 2026 -JOE THE SHOW ~ Durty Harry’s Stage
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February 20, 2026 -Scallywagz Band at Schooner Wharf Bar
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February 20, 2026 -Magic Of Frank Everhart at Schooner Wharf Bar
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February 20, 2026 -Gerd Rube at Tiki House Key West
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February 20, 2026 -Elle Haley ~ Rick’s Bar Downstairs Stage
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February 20, 2026 -The Original Key West Pub Crawl
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February 20, 2026 -Bone Island Haunted Pub Crawl & Ghost Tour
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February 20, 2026 -Victoria Leigh at Hank’s Hair of the Dog Saloon
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February 20, 2026Naked Karate Girls at Sloppy Joe’s Bar
Fishmonster Max- Daily Party Boat Fishing
Fishmonster Max offers a thrilling daily party boat fishing experience in Key West, perfect for families and groups. With its stable twin hulls, the boat…
Yoga on the Beach – Ft Zachary Taylor
Join a unique yoga experience with renowned instructors at Yoga on the Beach at Fort Zachary Taylor. Set against the backdrop of Key West’s historic…
Rolando Rojas at Sloppy Joe’s Bar
Experience the electrifying performance of Rolando Rojas at Sloppy Joe's Bar, where his charismatic stage presence and exceptional guitar skills captivate audiences. As a leading…
Story Time at the Key West Library
Join us every Tuesday at the Key West Library for an enchanting Storytime in the Garden with a captivating storyteller who brings tales to life.…
Distillery Tour – Key West Legal Rum Distillery
Experience an engaging distillery tour at Key West Legal Rum Distillery, featuring a skillful entertainer who brings the history and craft of rum making to…
Mojito Class by Key West Legal Rum Distillery – Min 4 people
There is a minimum of 4 people. Please contact mojitoclass@gmail.com to schedule. Please put how many people and date in the subject line. Join Key…
Glass Bottom Boat Cruise – Key West’s Window to the Sea
Experience the captivating Glass Bottom Boat tour in Key West, where our knowledgeable captain and crew offer an engaging eco-tour. Enjoy unparalleled views of North…
Tim Hollohan at Sloppy Joe’s Bar
Tim Hollohan, a talented musician originally from Columbia, South Carolina, captivates audiences at Sloppy Joe's Bar in Key West. Known for his engaging stage presence,…
Tony Baltimore at Schooner Wharf Bar
Tony Baltimore brings his vibrant musical talent to the Schooner Wharf Bar, infusing the historic Key West venue with captivating live performances. In a laid-back,…
Wynn Tayor ~ Rick’s Bar Downstairs Stage
Catch the captivating Wynn Taylor performing live at Rick's Bar Downstairs Stage. Known for his energetic and soulful performances, Wynn brings a dynamic blend of…
Mike Stack & D-Lew at Tiki House Key West
Experience an unforgettable night at Tiki House Key West with the dynamic duo, Mike Stack & D-Lew. Their electrifying performance blends captivating melodies and energizing…
Jockey Jord at Sunset Pier
Experience an unforgettable evening with Jockey Jord at Sunset Pier. This talented musician captivates audiences with lively tunes against the stunning backdrop of Key West's…
Pat Guadano and Friends at Hank’s Hair of the Dog Saloon
Pat Guadano and Friends bring an electrifying performance to Hank's Hair of the Dog Saloon in Key West. Known for his soulful voice and masterful…
Glass Bottom Boat Cruise – Key West’s Window to the Sea
Experience the magic of Key West's marine life aboard the Glass Bottom Boat. While our knowledgeable captain and crew guide you on an informative eco-tour,…
Jessie Cotton Stone at The Bull & Whistle Bar
Experience the captivating sounds of Jessie Cotton Stone at The Bull & Whistle Bar, a vibrant venue in Key West's Old Town. Known for engaging…
Fishmonster Max- Daily Party Boat Fishing
Fishmonster Max offers a thrilling daily party boat fishing experience in Key West, perfect for families and groups. With its stable twin hulls, the boat…
Reef Snorkeling, Dolphin Watch Eco Tour & Sunset Cruise
Join us for a vibrant aquatic adventure in Key West with our Reef Snorkeling, Dolphin Watch Eco Tour, and Sunset Cruise. Our passionate and friendly…
Joe the Show ~ Rick’s Bar Downstairs Stage
Experience an electrifying performance by Joe the Show at Rick's Bar Downstairs Stage. Known for his dynamic presence and musical prowess, Joe captivates audiences with…
Glass Bottom Boat Cruise – Key West’s Window to the Sea
Experience an unforgettable journey with Glass Bottom Boat - Key West's Window to the Sea. With an engaging and knowledgeable captain and crew, embark on…
Sunset Celebration at Mallory Square
The Sunset Celebration at Mallory Square in Key West is a must-see event. Renowned street performers captivate audiences with their vibrant talents, creating an unforgettable…
Rochi and Prince at Hank’s Hair of the Dog Saloon
Experience the captivating performance of Rochi and Prince at Hank's Hair of the Dog Saloon in Key West. Known for their dynamic stage presence and…
Pete & Larry Sloppy 2nds at Sloppy Joe’s Bar
Catch the dynamic duo Pete & Larry, better known as Sloppy 2nds, at the iconic Sloppy Joe's Bar. With their infectious humor and lively performances,…
Snacks and Five at Sunset Pier
Snacks and Five captivate audiences at Sunset Pier with vibrant live performances set against the stunning Key West sunset. Nestled where Duval Street meets the…
JOE THE SHOW ~ Durty Harry’s Stage
Experience the electrifying performance of Joe The Show at Durty Harry's Stage in Key West's iconic Rick's Entertainment Complex. Known for his dynamic musical talent…
Scallywagz Band at Schooner Wharf Bar
Experience the vibrant sounds of the Scallywagz Band at the Schooner Wharf Bar in Key West. Known for their lively performances, the band brings an…
Magic Of Frank Everhart at Schooner Wharf Bar
Experience the enchanting Magic of Frank Everhart at the Schooner Wharf Bar in Key West. Known for captivating performances, Everhart's illusions and sleight-of-hand tricks mesmerize…
Gerd Rube at Tiki House Key West
Experience the captivating sounds of Gerd Rube at Tiki House Key West. Renowned for his dynamic performances and eclectic music style, Gerd Rube brings a…
Elle Haley ~ Rick’s Bar Downstairs Stage
Experience the captivating performance of musician Elle Haley on the Downstairs Stage at Rick's Bar. Known for her dynamic presence and soulful sound, Elle creates…
The Original Key West Pub Crawl
Join The Original Key West Pub Crawl for a lively 2.5-hour adventure spotlighted by entertaining guides who infuse humor and energy into the experience. Enjoy…
Bone Island Haunted Pub Crawl & Ghost Tour
Join the Bone Island Haunted Pub Crawl & Ghost Tour for an enthralling evening led by a charismatic entertainer. With captivating narration, journey through America's…
Victoria Leigh at Hank’s Hair of the Dog Saloon
Victoria Leigh captivates audiences with her electrifying performances at Hank's Hair of the Dog Saloon. This talented musician brings her dynamic sound to Key West’s…
Naked Karate Girls at Sloppy Joe’s Bar
Experience the electrifying energy of the Naked Karate Girls, the ultimate party band hailing from Cincinnati. Known as The Best Band in the Galaxy, their…
Saturday, February 21, 2026
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February 21, 2026 -Daytime event to test 112, Stage A
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February 21, 2026 -Daytime event to test 113, Stage B
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February 21, 2026 -Fishmonster Max- Daily Party Boat Fishing
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February 21, 2026 -Yoga on the Beach – Ft Zachary Taylor
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February 21, 2026 -Prime of Life Yoga with Monica Haskell
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February 21, 2026 -Joe The Show at Sloppy Joe’s Bar
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February 21, 2026 -Distillery Tour – Key West Legal Rum Distillery
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February 21, 2026 -Mojito Class by Key West Legal Rum Distillery – Min 4 people
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February 21, 2026 -Glass Bottom Boat Cruise – Key West’s Window to the Sea
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February 21, 2026 -Nick Brownell at Schooner Wharf Bar
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February 21, 2026 -Sid The Bayou Kid at Sloppy Joe’s Bar
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February 21, 2026 -Zack Seemiller ~ Rick’s Bar Downstairs Stage
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February 21, 2026 -Victoria Leigh at Hank’s Hair of the Dog Saloon
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February 21, 2026 -Meghan Barter at Sunset Pier
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February 21, 2026 -Joe The Show at Tiki House Key West
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February 21, 2026 -Derek Dunbar at The Bull & Whistle Bar
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February 21, 2026 -Fishmonster Max- Daily Party Boat Fishing
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February 21, 2026 -Reef Snorkeling, Dolphin Watch Eco Tour & Sunset Cruise
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February 21, 2026 -Bradd Shadduck ~ Rick’s Bar Downstairs Stage
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February 21, 2026 -Glass Bottom Boat Cruise – Key West’s Window to the Sea
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February 21, 2026 -Sunset Celebration at Mallory Square
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February 21, 2026 -World Famous 801 Girls- 5pm Show
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February 21, 2026 -Kristen McNamara at Hank’s Hair of the Dog Saloon
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February 21, 2026 -Sharese Nicole at Tiki House Key West
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February 21, 2026 -Jeff Clark Band at Sloppy Joe’s Bar
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February 21, 2026 -Sunset Blues w/ Andy Westcott at Sunset Pier
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February 21, 2026 -Scallywagz Band at Schooner Wharf Bar
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February 21, 2026 -Magic Of Frank Everhart at Schooner Wharf Bar
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February 21, 2026 -The Linda Ronstadt Experience at Key West Theater
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February 21, 2026 -Karaoke at Two Friends Patio
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February 21, 2026 -Michael Corelto ~ Rick’s Bar Downstairs Stage
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February 21, 2026 -Elle Haley, Aaron Hudgins and Peyton Porter at Hank’s Hair of the Dog Saloon
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February 21, 2026Naked Karate Girls at Sloppy Joe’s Bar
Fishmonster Max- Daily Party Boat Fishing
Join Fishmonster Max for an unforgettable daily party boat fishing adventure in Key West, where entertainment meets the thrill of fishing. Whether it's a family…
Yoga on the Beach – Ft Zachary Taylor
Join a unique yoga experience with renowned instructors at Yoga on the Beach at Fort Zachary Taylor. Set against the backdrop of Key West’s historic…
Prime of Life Yoga with Monica Haskell
Join Monica Haskell for Prime of Life Yoga, a rejuvenating experience amidst the serene beauty of the Key West Tropical Forest & Botanical Garden. Known…
Joe The Show at Sloppy Joe’s Bar
Experience the dynamic performance of Joe The Show at Sloppy Joe's Bar in Key West. Known for his engaging presence and musical talent, Joe captivates…
Distillery Tour – Key West Legal Rum Distillery
Experience an engaging distillery tour at Key West Legal Rum Distillery, featuring a skillful entertainer who brings the history and craft of rum making to…
Mojito Class by Key West Legal Rum Distillery – Min 4 people
There is a minimum of 4 people. Please contact mojitoclass@gmail.com to schedule. Please put how many people and date in the subject line. Join Key…
Glass Bottom Boat Cruise – Key West’s Window to the Sea
Experience the captivating Glass Bottom Boat tour in Key West, where our knowledgeable captain and crew offer an engaging eco-tour. Enjoy unparalleled views of North…
Nick Brownell at Schooner Wharf Bar
Nick Brownell captivates audiences at the Schooner Wharf Bar in Key West with his vibrant live performances. Known for his engaging musical talents, Nick creates…
Sid The Bayou Kid at Sloppy Joe’s Bar
Sid The Bayou Kid, a charismatic musician from Thibodaux, LA, captivates audiences with his swamp-infused sound. With over 30 years of experience, Sid brings his…
Zack Seemiller ~ Rick’s Bar Downstairs Stage
Join musician Zack Seemiller at Rick's Bar's Downstairs Stage for an unforgettable evening of live music. Known for his captivating performances, Zack brings energy and…
Victoria Leigh at Hank’s Hair of the Dog Saloon
Victoria Leigh, a captivating musician, brings her enchanting melodies to Hank's Hair of the Dog Saloon in Key West. Known for her soulful vocals and…
Meghan Barter at Sunset Pier
Experience the enchanting melodies of musician Meghan Barter at Sunset Pier, where her captivating performance enhances the vibrant waterfront ambiance. Nestled in Key West's Ocean…
Joe The Show at Tiki House Key West
Experience the unforgettable Joe The Show at Tiki House Key West, where this talented musician captivates audiences with his electrifying performances. Known for his dynamic…
Derek Dunbar at The Bull & Whistle Bar
Experience the captivating sounds of Derek Dunbar at The Bull & Whistle Bar. Nestled in Key West’s vibrant Duval Street, this lively venue hosts Dunbar,…
Fishmonster Max- Daily Party Boat Fishing
Fishmonster Max offers a thrilling daily party boat fishing experience in Key West, perfect for families and groups. With its stable twin hulls, the boat…
Reef Snorkeling, Dolphin Watch Eco Tour & Sunset Cruise
Join an exhilarating aquatic adventure with the Reef Snorkeling, Dolphin Watch Eco Tour & Sunset Cruise. Led by our passionate and expert staff, enjoy thrilling…
Bradd Shadduck ~ Rick’s Bar Downstairs Stage
Experience the captivating performances of musician Bradd Shadduck at Rick's Bar Downstairs Stage in Key West. Known for his engaging live music, Bradd's dynamic style…
Glass Bottom Boat Cruise – Key West’s Window to the Sea
Experience an unforgettable journey with Glass Bottom Boat - Key West's Window to the Sea. With an engaging and knowledgeable captain and crew, embark on…
Sunset Celebration at Mallory Square
The Sunset Celebration at Mallory Square in Key West is a must-see event. Renowned street performers captivate audiences with their vibrant talents, creating an unforgettable…
World Famous 801 Girls- 5pm Show
The World Famous 801 Girls captivate audiences with their dazzling performances at the lively 801 Bourbon Bar in Old Town Key West. Known for their…
Kristen McNamara at Hank’s Hair of the Dog Saloon
Kristen McNamara lights up Hank's Hair of the Dog Saloon in Key West with her captivating performances. Known for her dynamic stage presence and musical…
Sharese Nicole at Tiki House Key West
Experience an unforgettable evening with the talented musician Sharese Nicole at Tiki House Key West. Known for her captivating performances and soulful melodies, Sharese Nicole…
Jeff Clark Band at Sloppy Joe’s Bar
Experience the vibrant sounds of the Jeff Clark Band at Sloppy Joe's Bar, Key West's historic music hotspot since 1937. Jeff Clark captivates with his…
Sunset Blues w/ Andy Westcott at Sunset Pier
Experience the soulful sounds of Andy Westcott as he brings his Sunset Blues performance to Sunset Pier. With the backdrop of Key West's stunning sunsets…
Scallywagz Band at Schooner Wharf Bar
Experience the vibrant rhythms of the Scallywagz Band at the Schooner Wharf Bar. Known for their eclectic mix of island tunes and lively performances, the…
Magic Of Frank Everhart at Schooner Wharf Bar
Experience the enchanting performance of magician Frank Everhart at Schooner Wharf Bar in Key West's Seaport. With mesmerizing tricks and captivating showmanship, Everhart transforms this…
The Linda Ronstadt Experience at Key West Theater
Experience the captivating tribute of The Linda Ronstadt Experience at the Key West Theater. This talented band brings Ronstadt's legendary hits to life, offering an…
Karaoke at Two Friends Patio
Experience unforgettable evenings at Two Friends Patio with lively karaoke sessions hosted by charismatic entertainers. Sing your heart out on the open-air patio, soaking in…
Michael Corelto ~ Rick’s Bar Downstairs Stage
Experience the electrifying performance of Michael Corelto at Rick's Bar Downstairs Stage. Known for his dynamic presence and captivating music, Michael brings the vibrant nightlife…
Elle Haley, Aaron Hudgins and Peyton Porter at Hank’s Hair of the Dog Saloon
Elle Haley captivates audiences with her soulful voice and engaging stage presence at Hank's Hair of the Dog Saloon in Key West. Joined by musicians…
Naked Karate Girls at Sloppy Joe’s Bar
Experience the electrifying Naked Karate Girls at Sloppy Joe's Bar, a must-see performance by Cincinnati's top band. Known as the best band in the galaxy,…
Sunday, February 22, 2026
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February 22, 2026 -Daytime event to test 114, Stage A
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February 22, 2026 -Daytime event to test 115, Stage B
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February 22, 2026 -Fishmonster Max- Daily Party Boat Fishing
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February 22, 2026 -Yoga on the Beach – Ft Zachary Taylor
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February 22, 2026 -Key West Artisan Market at Higgs Beach
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February 22, 2026 -Rolando Rojas at Sloppy Joe’s Bar
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February 22, 2026 -Mojito Class by Key West Legal Rum Distillery – Min 4 people
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February 22, 2026 -Distillery Tour – Key West Legal Rum Distillery
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February 22, 2026 -Glass Bottom Boat Cruise – Key West’s Window to the Sea
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February 22, 2026 -Mylo O’maolain at Schooner Wharf Bar
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February 22, 2026 -Behind Bootleg at Sloppy Joe’s Bar
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February 22, 2026 -Harley Ray ~ Rick’s Downstairs Stage
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February 22, 2026 -Big Bad Voodoo Daddy at Key West Theater
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February 22, 2026 -Farm Open House
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February 22, 2026 -Jon Hollywood at Tiki House Key West
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February 22, 2026 -Belle and McKenna at Sunset Pier
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February 22, 2026 -Victoria Leigh at Hank’s Hair of the Dog Saloon
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February 22, 2026 -Glass Bottom Boat Cruise – Key West’s Window to the Sea
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February 22, 2026 -David Warren at The Bull & Whistle Bar
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February 22, 2026 -Reef Snorkeling, Dolphin Watch Eco Tour & Sunset Cruise
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February 22, 2026 -801 Karaoke – Hosted by Jeff
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February 22, 2026 -Tea Dance at La Te Da
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February 22, 2026 -Trenton Chandler ~ Rick’s Bar Downstairs Stage
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February 22, 2026 -Glass Bottom Boat Cruise – Key West’s Window to the Sea
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February 22, 2026 -Sunset Celebration at Mallory Square
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February 22, 2026 -Caribe of Key West at El Meson de Pepes on Mallory Square
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February 22, 2026 -World Famous 801 Girls- 5pm Show
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February 22, 2026 -QMitch Drag Queen Bingo at 22&Co
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February 22, 2026 -Sunday Jazz at the Gardens
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February 22, 2026 -Jay Klein at Hank’s Hair of the Dog Saloon
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February 22, 2026 -Mojito at Sloppy Joe’s Bar
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February 22, 2026 -The Robert Albury Band at Sunset Pier
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February 22, 2026 -Jesse & Jillian at Schooner Wharf Bar
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February 22, 2026 -80s & 90s Trivia Night
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February 22, 2026 -Elle Haley at Tiki House Key West
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February 22, 2026 -Garrison Keillor And Erica Rhodes at Key West Theater
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February 22, 2026 -Magic Of Frank Everhart at Schooner Wharf Bar
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February 22, 2026 -Aaron Hudgins ~ Rick’s Bar Downstairs Stage
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February 22, 2026 -Sandra Lee at The Bull & Whistle Bar
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February 22, 2026 -Josh Kiser at Hank’s Hair of the Dog Saloon
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February 22, 2026Naked Karate Girls at Sloppy Joe’s Bar
Fishmonster Max- Daily Party Boat Fishing
Fishmonster Max offers a thrilling daily party boat fishing experience in Key West, perfect for families and groups. With its stable twin hulls, the boat…
Yoga on the Beach – Ft Zachary Taylor
Join a unique yoga experience with renowned instructors at Yoga on the Beach at Fort Zachary Taylor. Set against the backdrop of Key West’s historic…
Key West Artisan Market at Higgs Beach
The Key West Artisan Market at Higgs Beach offers more than just crafts; it's a lively event featuring talented local entertainers who captivate visitors with…
Rolando Rojas at Sloppy Joe’s Bar
Rolando Rojas, a captivating and highly sought-after musician, electrifies Sloppy Joe's Bar with his exceptional guitar skills and charismatic stage presence. Known as a top…
Mojito Class by Key West Legal Rum Distillery – Min 4 people
There is a minimum of 4 people. Please contact mojitoclass@gmail.com to schedule. Please put how many people and date in the subject line. Join Key…
Distillery Tour – Key West Legal Rum Distillery
Experience an engaging distillery tour at Key West Legal Rum Distillery, featuring a skillful entertainer who brings the history and craft of rum making to…
Glass Bottom Boat Cruise – Key West’s Window to the Sea
Experience the captivating Glass Bottom Boat tour in Key West, where our knowledgeable captain and crew offer an engaging eco-tour. Enjoy unparalleled views of North…
Mylo O’maolain at Schooner Wharf Bar
Mylo O'Maolain captivates audiences at the Schooner Wharf Bar with his soulful melodies and vibrant energy. This talented musician transforms the historic Key West venue…
Behind Bootleg at Sloppy Joe’s Bar
Experience the captivating sounds of Behind Bootleg at the iconic Sloppy Joe's Bar, a vibrant venue on Duval Street in Key West. Known for its…
Harley Ray ~ Rick’s Downstairs Stage
Experience an electrifying night with musician Harley Ray at Rick's Downstairs Stage in Key West. Renowned for his captivating performances, Harley Ray brings a dynamic…
Big Bad Voodoo Daddy at Key West Theater
Join Big Bad Voodoo Daddy at the Key West Theater for an unforgettable night of swing and jazz. Known for their high-energy performances and exceptional…
Farm Open House
Experience captivating entertainment at the Farm Open House in Key West. Held at the Monroe County Sheriff's Office Animal Farm, this community-focused event features live…
Jon Hollywood at Tiki House Key West
Experience an unforgettable evening with Jon Hollywood at Tiki House Key West. Renowned for his captivating performances and magnetic stage presence, Jon delivers a vibrant…
Belle and McKenna at Sunset Pier
Belle and McKenna, a dynamic musical duo, captivate audiences at Sunset Pier with their vibrant performances and eclectic repertoire. Their live music creates an unforgettable…
Victoria Leigh at Hank’s Hair of the Dog Saloon
Victoria Leigh captivates audiences at Hank's Hair of the Dog Saloon with her dynamic performances. As a talented musician, she brings vibrant energy to Key…
Glass Bottom Boat Cruise – Key West’s Window to the Sea
Experience the magic of Key West's marine life aboard the Glass Bottom Boat. While our knowledgeable captain and crew guide you on an informative eco-tour,…
David Warren at The Bull & Whistle Bar
Join the lively atmosphere at The Bull & Whistle Bar on Duval Street, where David Warren captivates audiences with his engaging live music performances. Known…
Reef Snorkeling, Dolphin Watch Eco Tour & Sunset Cruise
Join us for a vibrant aquatic adventure in Key West with our Reef Snorkeling, Dolphin Watch Eco Tour, and Sunset Cruise. Our passionate and friendly…
801 Karaoke – Hosted by Jeff
Join the unforgettable Sunday karaoke at 801 Bourbon Bar, hosted by the charismatic Jeff. Known for his engaging personality, Jeff takes center stage, making each…
Tea Dance at La Te Da
Experience a vibrant evening at Tea Dance at La Te Da, featuring the incredible Randy Roberts. Delight in raunchy drag performances and masterful impersonations of…
Trenton Chandler ~ Rick’s Bar Downstairs Stage
Trenton Chandler, a talented country musician from Shallowater, Texas, captivates audiences with his heartfelt performances. Drawing inspiration from legends like Elvis and Waylon Jennings, Trenton…
Glass Bottom Boat Cruise – Key West’s Window to the Sea
Experience an unforgettable journey with Glass Bottom Boat - Key West's Window to the Sea. With an engaging and knowledgeable captain and crew, embark on…
Sunset Celebration at Mallory Square
The Sunset Celebration at Mallory Square in Key West is a must-see event. Renowned street performers captivate audiences with their vibrant talents, creating an unforgettable…
Caribe of Key West at El Meson de Pepes on Mallory Square
Caribe of Key West delivers an electrifying performance at El Meson de Pepe on Mallory Square, infusing the vibrant atmosphere with lively music. As you…
World Famous 801 Girls- 5pm Show
The World Famous 801 Girls captivate audiences with their dazzling performances at the lively 801 Bourbon Bar in Old Town Key West. Known for their…
QMitch Drag Queen Bingo at 22&Co
Experience an unforgettable night with QMitch Drag Queen Bingo at 22&Co in Old Town Key West. Renowned for dazzling performances and unmatched charisma, QMitch transforms…
Sunday Jazz at the Gardens
Experience the soulful melodies of Sunday Jazz at the Gardens, where talented musicians serenade guests in the enchanting ambiance of The Gardens Hotel. Amidst lush…
Jay Klein at Hank’s Hair of the Dog Saloon
Experience the captivating sounds of musician Jay Klein at Hank's Hair of the Dog Saloon. Known for his dynamic performances, Klein brings energy and talent…
Mojito at Sloppy Joe’s Bar
Mojito energizes Sloppy Joe's Bar with their vibrant, upbeat music, infusing Latin flair and rhythm that gets everyone on their feet and dancing. Located on…
The Robert Albury Band at Sunset Pier
Experience the vibrant sounds of The Robert Albury Band at Sunset Pier, where their lively performances set the perfect backdrop against Key West's stunning sunsets.…
Jesse & Jillian at Schooner Wharf Bar
Experience the captivating sounds of Jesse & Jillian at Schooner Wharf Bar, where the dynamic duo brings their unique musical flair to Key West’s historic…
80s & 90s Trivia Night
Join 80s & 90s Trivia Night at The Retro Room in Old Town, Key West, where an engaging entertainer takes you on a nostalgic journey.…
Elle Haley at Tiki House Key West
Experience the captivating performance of musician Elle Haley at Tiki House Key West. Known for her soulful melodies and vibrant stage presence, Elle enchants audiences…
Garrison Keillor And Erica Rhodes at Key West Theater
Join renowned entertainer Garrison Keillor alongside the talented Erica Rhodes at the Key West Theater for an unforgettable evening. Keillor, famed for his captivating storytelling…
Magic Of Frank Everhart at Schooner Wharf Bar
Experience the enchanting Magic of Frank Everhart at Schooner Wharf Bar in Key West's Seaport. A master magician, Everhart captivates audiences with mesmerizing illusions and…
Aaron Hudgins ~ Rick’s Bar Downstairs Stage
Experience the captivating performance of musician Aaron Hudgins at Rick's Bar Downstairs Stage in Key West. Known for his engaging presence, Aaron brings a dynamic…
Sandra Lee at The Bull & Whistle Bar
Experience the captivating performance of musician Sandra Lee at The Bull & Whistle Bar in Key West’s Old Town. Renowned for her engaging live shows,…
Josh Kiser at Hank’s Hair of the Dog Saloon
Catch the dynamic performance of musician Josh Kiser at Hank's Hair of the Dog Saloon in Key West. Known for his engaging live shows, Josh…
Naked Karate Girls at Sloppy Joe’s Bar
Experience the electrifying energy of the Naked Karate Girls, the ultimate party band hailing from Cincinnati. Known as The Best Band in the Galaxy, their…