The Tiki Bombs at Tiki House Key West
The Tiki Bombs perform at Tiki House Key West, captivating audiences with energetic performances and tropical-inspired tunes. Known for blending traditional island melodies with modern…
Free
58 events found.
Events for April 5, 2026
Ongoing
Mike Veal Band at Hog’s Breath Saloon
The Mike Veal Band electrifies Hog's Breath Saloon with their dynamic blend of Blues, Rock, and Funk. Known for their diverse musical backgrounds, they deliver…
Free
Karaoke at Bobby’s Monkey Bar
Join the vibrant nightlife at Bobby's Monkey Bar for unforgettable karaoke sessions hosted by dynamic entertainers who know how to engage the crowd. Set in…
Crownz at Sloppy Joe’s Bar
Crownz, the energetic pop rock band from Tampa, electrifies audiences at Sloppy Joe's Bar in Key West. Known for their captivating performances and catchy tunes,…
Free
Riptide Riot at Irish Kevin’s Bar
Experience the electrifying energy of Riptide Riot, the dynamic power duo performing weekly at Irish Kevin's Bar in Key West. With Jim Simonian on drums…
Free
Fishmonster Max- Daily Party Boat Fishing
Join the Fishmonster Max daily party boat fishing excursion at A & B Marina in Key West's historic seaport. While the details of the entertainer…
$85.00
Yoga on the Beach – Ft Zachary Taylor
Experience tranquility with Yoga on the Beach at Fort Zachary Taylor in Key West. Despite the lack of a specific entertainer, this serene outdoor session…
$20
Victoria Leigh at Sloppy Joe’s Bar
Experience the captivating energy of Victoria Leigh at Sloppy Joe's Bar in Key West. Known for her feel-good covers, mashups, and original songs, Victoria performs…
Free
Key West Artisan Market at Higgs Beach
The Key West Artisan Market at Higgs Beach is a vibrant gathering featuring local artisans and diverse vendors. A highlight of the event is the…
Local’s Day at The Key West Tropical Forest & Botanical Garden
Local's Day at The Key West Tropical Forest & Botanical Garden offers a vibrant experience featuring live performances by talented local musicians. Amidst the lush…
Krystal King at Mac’s Place
Krystal King captivates audiences at Mac's Place with her dynamic stage presence and exceptional leadership in entertainment. Renowned for her innovative approach, Krystal transforms every…
Free
Marjory Lee at Rams Head Southernmost
Experience the soulful sounds of Marjory Lee at Rams Head Southernmost. A Key West native and Fantasy Fest Queen 2024, Marjory captivates audiences with her…
Free
Bradd Shadduck at Irish Kevin’s Bar
Experience a lively night at Irish Kevin's Bar with the entertaining Bradd Shadduck, a talented musician who electrifies the stage with his captivating performances. As…
Free
Distillery Tour – Key West Legal Rum Distillery
Explore the Key West First Legal Rum Distillery, nestled in the Historic Seaport. Delight in daily tours and rum samples while embracing vibrant nightlife vibes.…
Free
Mojito Class by Key West Legal Rum Distillery – Min 4 people
Join the Mojito Class at Key West First Legal Rum Distillery, where a charismatic entertainer will guide you through a lively mojito-making experience. Delight in…
$75.00
Glass Bottom Boat Cruise – Key West’s Window to the Sea
Join the Glass Bottom Boat Cruise in Key West for an unforgettable journey beneath the sea. While soaking in vibrant marine life through crystal-clear waters,…
$69.95
Aaron Blumer at Hog’s Breath Saloon
Aaron Blumer, a free-spirited musician, graces Hog's Breath Saloon with his adventurous and spontaneous spirit. Known for his fluidity in life and music, Aaron captivates…
Free
Harley Ray at Rick’s Downstairs Stage
Experience a night of authentic musical depth with Harley Ray at Rick's Downstairs Stage. An innovative songwriter, Ray captivates audiences with melodies that resonate deeply…
Free
Brian Roberts at Sloppy Joe’s Bar
Experience the captivating live performances of singer/songwriter Brian Roberts at Sloppy Joe's Bar, Key West. Every Tuesday and Wednesday afternoon, Brian mesmerizes audiences with his…
Free
Mylo O’Maolain at Schooner Wharf Bar
Mylo O'Maolain, an Irish-born musician, lights up the Schooner Wharf Bar in Key West with his vibrant and soulful performances. Known for blending Irish traditions…
Free
Rick Fusco Trio at Green Parrot Bar
Experience the dynamic energy of the Rick Fusco Trio at the Green Parrot Bar in Key West. Rick Fusco, a talented musician, leads the trio…
Free
Victoria Leigh at Hank’s Hair of the Dog Saloon
Victoria Leigh is a dynamic musician in the Florida Keys, known for her infectious energy and feel-good music. Performing over 350 live shows each year,…
Free
Glass Bottom Boat Cruise – Key West’s Window to the Sea
The Glass Bottom Boat Cruise in Key West offers a unique marine adventure, enhanced by a captivating entertainer who brings the vibrant sea life into…
$69.95
Jeff Harris at Irish Kevin’s Bar
At Irish Kevin’s Bar, Jeff Harris captivates audiences with his dynamic blend of music and comedy. This talented American artist, renowned for his heartfelt lyrics…
Free
Aaron Hudgins at Tiki House Key West
Aaron Hudgins brings his musical talents to Tiki House Key West, enchanting audiences with his captivating performances. As a skilled musician, Aaron creates an unforgettable…
Free
Rick Fusco Trio at Green Parrot Bar
Experience the captivating sounds of the Rick Fusco Trio at the legendary Green Parrot Bar. Known for his magnetic presence and exceptional musical talent, Rick…
Free
Reef Snorkeling, Dolphin Watch Eco Tour & Sunset Cruise
Experience an unforgettable adventure with Sunset Watersports' Reef Snorkeling, Dolphin Watch Eco Tour, and Sunset Cruise in Key West. Guided by knowledgeable and engaging staff,…
$79.95
Tea Dance at La Te Da
Experience the vibrant Tea Dance at La Te Da in Key West, where the spotlight is on the extraordinary performances by drag star Randy Roberts.…
Free
Glass Bottom Boat Cruise – Key West’s Window to the Sea
Embark on the Glass Bottom Boat Cruise in Key West for an unforgettable maritime adventure. While the vibrant marine life and crystal-clear waters captivate, it's…
$69.95
Trenton Chandler at Rick’s Bar Downstairs Stage
Trenton Chandler, a talented country musician hailing from Shallowater, Texas, is set to light up Rick's Bar Downstairs Stage. With roots deeply entrenched in the…
Free
801 Karaoke – Hosted by Jeff
Join the vibrant atmosphere of 801 Bourbon Bar in Old Town Key West for an unforgettable karaoke night hosted by the charismatic Jeff. Known for…
Free
Harley Ray & Savanna Chestnut at Hog’s Breath Saloon
Experience the soulful sounds of Harley Ray and Savanna Chestnut at Hog's Breath Saloon. Harley Ray captivates audiences with his heartfelt songwriting, weaving melodies that…
Free
World Famous 801 Girls- 5pm Show
Experience the charismatic performances of the World Famous 801 Girls during the 5pm show at 801 Bourbon Bar, nestled in Old Town Key West. These…
QMitch Drag Queen Bingo at 22&Co
QMitch captivates audiences at 22&Co in Key West with her vibrant drag queen bingo performances. Known for her dynamic presence and charismatic flair, QMitch transforms…
Free
Sunday Jazz at the Gardens
Sunday Jazz at the Gardens features captivating performances by talented jazz musicians in a lush, tropical setting at The Gardens Hotel in Key West. Enjoy…
Free
Jay Klein at Hank’s Hair of the Dog Saloon
Experience the dynamic talent of Jay Klein, an accomplished musician and tech-savvy entrepreneur, at Hank's Hair of the Dog Saloon in Key West. Enjoy his…
Free
Rick Fusco at Rams Head Southernmost
Rick Fusco, a talented musician, brings his captivating performances to Rams Head Southernmost. Known for his engaging live shows, Rick entertains audiences with a diverse…
Free
Caribe of Key West at El Meson de Pepes on Mallory Square
Experience the vibrant rhythms of Caribe of Key West at El Meson de Pepe's on Mallory Square. This talented band captivates audiences with their energetic…
Sunset Celebration at Mallory Square
Experience the lively Sunset Celebration at Mallory Square, where street performers and entertainers take center stage. Marvel at the famous cat man's astonishing feline tricks…
Free
The Quickening Soundcheck Set at Green Parrot Bar
The Quickening lights up the iconic Green Parrot Bar with their captivating soundcheck set, showcasing electrifying performances that blend energy and charisma. Known for their…
Free
Pete & Larry Sloppy 2nds at Sloppy Joe’s Bar
Experience the eclectic talents of Pete & Larry Sloppy 2nds at Sloppy Joe's Bar in Key West. This dynamic duo captivates audiences with their unique…
Free
Jerome & Wynn at The Alamo Key West
Experience the captivating performance of Jerome & Wynn at The Alamo Key West. This dynamic duo, renowned for their innovative problem-solving and creative collaboration, brings…
Free
Oren Polak at Irish Kevin’s Bar
Oren Polak, a dynamic musician and band leader, captivates audiences at Irish Kevin's Bar with his engaging performances and distinctive sound. Known for bringing Music…
Free
80s & 90s Trivia Night
Join us for an unforgettable 80s & 90s Trivia Night at The Retro Room in Old Town Key West. Our charismatic entertainer will guide you…
Free
Sam Carlson at Schooner Wharf Bar
Sam Carlson, a talented musician from Pennsylvania, brings a soulful-folk and Americana vibe to the Schooner Wharf Bar. With a background in Gospel hymns, his…
Free
DJ Marty at Red Garter Saloon Stage
DJ Marty is a dynamic music curator performing at the Red Garter Saloon Stage. Renowned for his electrifying performances and seamless mixing, he captivates audiences…
Free
Andy Mauerman at Halo Rooftop Lounge Bar at The Saint
Andy Mauerman brings his philosophy of experiential living to life at Halo Rooftop Lounge Bar. As a musician who values experiences over material possessions, Andy…
Free
Magic Of Frank Everhart at Schooner Wharf Bar
Experience the enchanting Magic of Frank Everhart, a legendary magician captivating audiences at Schooner Wharf Bar. Renowned for his innovative tricks and mesmerizing storytelling, Everhart’s…
Free
Elle Haley at Tiki House Key West
Elle Haley, a vibrant musician from the Florida Keys, enchants audiences with her captivating and soulful performances at Tiki House Key West. Known for creating…
Free
Aaron Hudgins at Rick’s Bar Downstairs Stage
Experience the mesmerizing performance of Aaron Hudgins at Rick's Bar Downstairs Stage in Key West. Known for his captivating musical prowess, Aaron brings a blend…
Free
DJ Kori at Rick’s Bar Upstairs Stage
Step into Rick's Bar Upstairs Stage for an unforgettable night with DJ Kori. Renowned since 1993 for exceptional mobile DJ and karaoke services, DJ Kori…
Free
Durtbags at Durty Harry’s Stage
Experience the electrifying energy of The Durtbags at Durty Harry's Stage in Key West's vibrant Rick's Entertainment Complex. As the biggest party rock band in…
Free
Cliff Cody at Hank’s Hair of the Dog Saloon
Experience the soulful sounds of Cliff Cody, a Texas-born country singer/songwriter, at Hank's Hair of the Dog Saloon. Known for his powerful voice and relatable…
Free
Mike Veal Band at Hog’s Breath Saloon
The Mike Veal Band delivers an electrifying performance at Hog's Breath Saloon, captivating audiences with a dynamic mix of Blues, Rock, and Funk. Their diverse…
Free
Karaoke at Bobby’s Monkey Bar
Join the vibrant island atmosphere at Bobby's Monkey Bar for a night of karaoke fun. With talented local performers leading the charge, the lively ambiance…
Tim Bradach at Irish Kevin’s Bar
Tim Bradach energizes the crowd at Irish Kevin's Bar with his captivating performance and dynamic musical talent. Nestled in the vibrant heart of Old Town…
Free
Crownz at Sloppy Joe’s Bar
Experience the electrifying performance of Crownz at Sloppy Joe's Bar, a Key West staple since 1933. This dynamic pop rock band from Tampa energizes the…
Free
Karaoke w/ Jason at Rick’s Bar Downstairs Stage
Experience an unforgettable night with DJ Jason at Rick's Bar's Downstairs Stage. Renowned for his electrifying beats and seamless mixes, Jason brings his dynamic energy…
Free