7 events found.
Week of Events
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 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 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,…
DJ Todd ~ Red Garter Saloon Stage
Renowned DJ Todd electrifies the crowd at the Red Garter Saloon Stage within Rick's Entertainment Complex, Key West's nightlife centerpiece. His dynamic mixes and infectious…
Free
DJ Duke ~ Rick’s Bar Upstairs Stage
Experience the electrifying beats of DJ Duke at Rick's Bar Upstairs Stage, located in the vibrant heart of Old Town Key West. Known for his…
Free
CRANK SINATRA~ Durty Harry’s Stage
Experience the electrifying performance of Krank Sinatra at Durty Harry's Stage in Rick's Entertainment Complex. Known for their dynamic stage presence, the band delivers an…
Free
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/ Davis ~ Rick’s Bar Downstairs Stage
Join Davis for an unforgettable karaoke night at Rick's Bar Downstairs Stage in Key West. Known for his engaging and lively performances, Davis invites you…
Free
DJ Marty ~ Red Garter Saloon Stage
Experience the electrifying beats of DJ Marty live on the Red Garter Saloon Stage at Rick's Entertainment Complex in Old Town Key West. Renowned for…
Free
DJ Chaka ~ Rick’s Bar Upstairs Stage
Experience the electrifying beats of DJ Chaka at Rick's Bar Upstairs Stage. Known for his dynamic mixes and infectious energy, DJ Chaka transforms the largest…
Free
DURTBAGS~ Durty Harry’s Stage
Experience the electrifying energy of Key West’s ultimate party band, The Durtbags, at Durty Harry's Stage. Rocking the heart of Rick's Entertainment Complex, their dynamic…
Free
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…
Free
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 lively energy and engaging presence, Jason turns the stage…
Free
Elle Haley at Hog’s Breath Saloon
Experience a captivating evening with Elle Haley at Hog's Breath Saloon in Key West's vibrant Mallory Square District. Known for her mesmerizing performances, Elle brings…
Free
DJ Marty ~ Red Garter Saloon Stage
Experience the vibrant beats of DJ Marty at the Red Garter Saloon Stage in Rick's Entertainment Complex, Old Town Key West. Renowned for his electrifying…
Free
LuffKiD at General Horseplay
Experience the magnetic energy of LuffKiD at General Horseplay in Old Town Key West. Known for his captivating performances, LuffKiD brings an electrifying blend of…
Free
DJ Duke ~ Rick’s Bar Upstairs Stage
Experience the electrifying beats of DJ Duke at Rick's Bar Upstairs Stage, where this dynamic DJ sets the night ablaze with his unparalleled mixing skills.…
Free
DURTBAGS ~ Durty Harry’s Stage
Experience the electrifying performances of The Durtbags, Key West's premier party rock band, at Durty Harry's Stage. Enjoy their captivating live shows every Thursday through…
Free
Chase Shepard Band at The Bull & Whistle Bar
Experience the dynamic energy of the Chase Shepard Band at The Bull & Whistle Bar in Key West. Known for their captivating performances and musical…
Free
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 sounds of Tequila Time Machine at General Horseplay in Key West. This dynamic band delivers an unforgettable night of music, perfectly complementing…
Free
DJ Hazard at Tiki House Key West
Experience an electrifying night with DJ Hazard at Tiki House Key West. Renowned for his dynamic soundscapes and vibrant beats, DJ Hazard commands the crowd…
Free
Karaoke w/ Jason ~ Rick’s Bar Downstairs Stage
Join Jason for an electrifying karaoke night at Rick's Bar Downstairs Stage in Key West's largest entertainment complex. Jason's dynamic energy and engaging stage presence…
Free
Sheldon Benton at Hog’s Breath Saloon
Sheldon Benton captivates audiences at Hog's Breath Saloon in Key West with his dynamic live performances. Known for his energetic stage presence and versatile musical…
Free
DJ Marty ~ Red Garter Saloon Stage
Experience the electrifying beats of DJ Marty at the Red Garter Saloon Stage in Rick's Entertainment Complex. Known for his dynamic mixes and vibrant energy,…
Free
Zach Lovering at General Horseplay
Zach Lovering captivates audiences at General Horseplay, infusing the lively cocktail bar with his dynamic musical performances. Known for his engaging presence and vibrant sound,…
Free
DJ Chaka ~ Rick’s Bar Upstairs Stage
Experience the electrifying beats of DJ Chaka at Rick's Bar Upstairs Stage in Key West. Known for his dynamic soundscapes and vibrant mixes, DJ Chaka…
Free
DURTBAGS ~ Durty Harry’s Stage
Experience the ultimate Key West nightlife with The Durtbags, the island’s premier party rock band, lighting up Durty Harry's Stage at Rick's Entertainment Complex. Catch…
Free
DJ at Hinote at General Horseplay
Experience electrifying sets from the talented DJ at Hinote at General Horseplay. Known for their dynamic mixes and infectious energy, this DJ turns the vibrant…
Free
Chase Shepard Band at The Bull & Whistle Bar
Experience the electrifying Chase Shepard Band live at The Bull & Whistle Bar, Key West’s iconic nightlife spot. Dive into a night of energetic performances,…
Free
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,…
Mike Stack & D-Lew at General Horseplay
Join Mike Stack & D-Lew at General Horseplay in Old Town Key West for an unforgettable night of live music. Known for their energizing performances…
Free
Karaoke w/ Jason ~ Rick’s Bar Downstairs Stage
Join Jason for an unforgettable karaoke night at Rick's Bar on the Downstairs Stage. As a charismatic entertainer, Jason brings energy and excitement, transforming the…
Free
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…
Free
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…
Free
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…
Free
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…
Free
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…
Free
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 Downstairs Stage. As the heart and soul of the night, Jason brings infectious energy that…
Free
Monday, February 9, 2026
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February 9, 2026 -World Famous 801 Girls- 5pm Show
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February 9, 2026 -Charity Bingo at The Green Parrot
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…
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…
Free
Tuesday, February 10, 2026
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February 10, 2026 -World Famous 801 Girls- 5pm Show
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…
Wednesday, February 11, 2026
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February 11, 2026 -World Famous 801 Girls- 5pm Show
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…
Thursday, February 12, 2026
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February 12, 2026 -Trenton Chandler ~ Rick’s DownStairs Stage
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February 12, 2026 -Wolf Love at Sloppy Joe’s Bar
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February 12, 2026 -Jeff Harris ~ Rick’s Bar Downstairs Stage
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February 12, 2026 -World Famous 801 Girls- 5pm Show
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February 12, 2026 -Joe the Show ~ Rick’s Bar Downstairs Stage
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February 12, 2026LaurLea & Tripp Fabulous at Sloppy Joe’s Bar
Trenton Chandler ~ Rick’s DownStairs Stage
Experience the electrifying performance of Trenton Chandler at Rick's DownStairs Stage in Key West. A passionate country musician and songwriter from Shallowater, Texas, Trenton draws…
Free
Wolf Love at Sloppy Joe’s Bar
Experience the captivating performance of Wolf Love at the historic Sloppy Joe's Bar in Key West. As part of Put-In-Bay Days, Wolf Love fills the…
Free
Jeff Harris ~ Rick’s Bar Downstairs Stage
Experience the captivating sounds of musician Jeff Harris as he takes the stage at Rick's Bar Downstairs, nestled in Key West's vibrant Old Town. Known…
Free
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…
Joe the Show ~ Rick’s Bar Downstairs Stage
Experience the electrifying performance of Joe the Show at Rick's Bar Downstairs Stage. Known for his dynamic presence and captivating musical talent, Joe brings an…
Free
LaurLea & Tripp Fabulous at Sloppy Joe’s Bar
Join LaurLea & Tripp Fabulous at Sloppy Joe's Bar for an unforgettable night of party rock hits from Philadelphia! Performing live from 10:00pm-2:00am, this energetic…
Free
Friday, February 13, 2026
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February 13, 2026 -Wynn Tayor ~ Rick’s Bar Downstairs Stage
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February 13, 2026 -Jessie Cotton Stone at The Bull & Whistle Bar
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February 13, 2026 -Joe the Show ~ Rick’s Bar Downstairs Stage
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February 13, 2026 -World Famous 801 Girls- 5pm Show
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February 13, 2026 -Barrett Thomas at Hank’s Hair of the Dog Saloon
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February 13, 2026 -JOE THE SHOW ~ Durty Harry’s Stage
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February 13, 2026 -Turner Harrison at Tiki House Key West
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February 13, 2026 -Elle Haley ~ Rick’s Bar Downstairs Stage
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February 13, 2026 -Victoria Leigh at Hank’s Hair of the Dog Saloon
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February 13, 2026LaurLea & Tripp Fabulous at Sloppy Joe’s Bar
Wynn Tayor ~ Rick’s Bar Downstairs Stage
Experience the captivating performance of musician Wynn Taylor at Rick's Bar Downstairs Stage in Key West's iconic Rick's Entertainment Complex. Known for his engaging and…
Free
Jessie Cotton Stone at The Bull & Whistle Bar
Experience the electrifying performance of Jessie Cotton Stone at The Bull & Whistle Bar in Key West. Known for his soulful melodies and dynamic stage…
Free
Joe the Show ~ Rick’s Bar Downstairs Stage
Experience the electrifying performance of Joe the Show at Rick's Bar Downstairs Stage in Key West. As a captivating musician, Joe brings unparalleled energy and…
Free
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…
Barrett Thomas at Hank’s Hair of the Dog Saloon
Experience the captivating performance of musician Barrett Thomas at Hank's Hair of the Dog Saloon in Key West. Known for his engaging live music, Barrett's…
Free
JOE THE SHOW ~ Durty Harry’s Stage
Experience the electrifying performance of Joe The Show at Durty Harry's Stage, located within Rick's Entertainment Complex. Known for captivating audiences with his dynamic musical…
Free
Turner Harrison at Tiki House Key West
Experience an unforgettable evening at Tiki House Key West with the vibrant Turner Harrison. Known for his captivating performances and dynamic stage presence, Turner effortlessly…
Free
Elle Haley ~ Rick’s Bar Downstairs Stage
Experience the captivating performance of musician Elle Haley at Rick's Bar Downstairs Stage. Known for her dynamic presence and mesmerizing vocals, Elle brings an unforgettable…
Free
Victoria Leigh at Hank’s Hair of the Dog Saloon
Victoria Leigh captivates audiences at Hank's Hair of the Dog Saloon with her mesmerizing musical performances. Known for her soulful voice and vibrant stage presence,…
Free
LaurLea & Tripp Fabulous at Sloppy Joe’s Bar
LaurLea & Tripp Fabulous, a dynamic party rock band from Philadelphia, light up the stage at Sloppy Joe's Bar from 10:00 pm to 2:00 am.…
Free
Saturday, February 14, 2026
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February 14, 2026 -Zack Seemiller ~ Rick’s Bar Downstairs Stage
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February 14, 2026 -Marjorie Lee at Hank’s Hair of the Dog Saloon
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February 14, 2026 -Derek Dunbar at The Bull & Whistle Bar
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February 14, 2026 -Eric Ripper at Hank’s Hair of the Dog Saloon
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February 14, 2026 -Bradd Shadduck ~ Rick’s Bar Downstairs Stage
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February 14, 2026 -World Famous 801 Girls- 5pm Show
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February 14, 2026 -Kristen McNamara at Hank’s Hair of the Dog Saloon
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February 14, 2026 -Michael Corelto ~ Rick’s Bar Downstairs Stage
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February 14, 2026 -Aaron Hudgins and Pierce August at Hank’s Hair of the Dog Saloon
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February 14, 2026LaurLea & Tripp Fabulous at Sloppy Joe’s Bar
Zack Seemiller ~ Rick’s Bar Downstairs Stage
Experience the captivating musical artistry of Zack Seemiller at Rick's Bar Downstairs Stage. Known for his dynamic performances and engaging presence, Zack delivers an unforgettable…
Free
Marjorie Lee at Hank’s Hair of the Dog Saloon
Marjorie Lee enchants audiences at Hank's Hair of the Dog Saloon with her captivating musical performances. Known for her soulful voice and dynamic stage presence,…
Free
Derek Dunbar at The Bull & Whistle Bar
Experience the captivating musical talents of Derek Dunbar at The Bull & Whistle Bar in Key West’s vibrant Old Town. Known for his electrifying performances,…
Free
Eric Ripper at Hank’s Hair of the Dog Saloon
Experience the electrifying performance of Eric Ripper at Hank's Hair of the Dog Saloon, a lively hotspot in Key West. As a captivating musician, Eric…
Free
Bradd Shadduck ~ Rick’s Bar Downstairs Stage
Experience the captivating performance of musician Bradd Shadduck at Rick's Bar Downstairs Stage, where his engaging melodies and dynamic presence light up the venue. Nestled…
Free
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 brings her captivating musical talent to Hank's Hair of the Dog Saloon, offering an unforgettable live performance. Known for her dynamic voice and…
Free
Michael Corelto ~ Rick’s Bar Downstairs Stage
Experience the captivating talent of Michael Corelto at Rick's Bar Downstairs Stage in Key West's vibrant entertainment complex. Known for his electrifying performances, Corelto brings…
Free
Aaron Hudgins and Pierce August at Hank’s Hair of the Dog Saloon
Aaron Hudgins energizes Hank's Hair of the Dog Saloon in Key West with his captivating musical performances, setting the stage for an unforgettable evening. This…
Free
LaurLea & Tripp Fabulous at Sloppy Joe’s Bar
Experience the electrifying performance of LaurLea & Tripp Fabulous at Sloppy Joe's Bar in Key West. This Philadelphia-based party rock band takes the stage from…
Free
Sunday, February 15, 2026
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February 15, 2026 -Harley Ray ~ Rick’s Downstairs Stage
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February 15, 2026 -Sid Ordoyne at Hank’s Hair of the Dog Saloon
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February 15, 2026 -The Reverend TJ at Tiki House Key West
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February 15, 2026 -David Warren at The Bull & Whistle Bar
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February 15, 2026 -801 Karaoke – Hosted by Jeff
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February 15, 2026 -Tea Dance at La Te Da
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February 15, 2026 -Trenton Chandler ~ Rick’s Bar Downstairs Stage
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February 15, 2026 -World Famous 801 Girls- 5pm Show
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February 15, 2026 -QMitch Drag Queen Bingo at 22&Co
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February 15, 2026 -Pierce August at Hank’s Hair of the Dog Saloon
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February 15, 2026 -Aaron Hudgins ~ Rick’s Bar Downstairs Stage
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February 15, 2026 -Sandra Lee at The Bull & Whistle Bar
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February 15, 2026 -Cliff Cody at Hank’s Hair of the Dog Saloon
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February 15, 2026LaurLea & Tripp Fabulous at Sloppy Joe’s Bar
Harley Ray ~ Rick’s Downstairs Stage
Experience the electrifying performance of musician Harley Ray at Rick's Downstairs Stage in Old Town Key West. Known for his dynamic sound and captivating presence,…
Free
Sid Ordoyne at Hank’s Hair of the Dog Saloon
Sid Ordoyne brings his captivating musical talent to Hank's Hair of the Dog Saloon, enchanting guests with his soulful performances. Set in the vibrant ambiance…
Free
The Reverend TJ at Tiki House Key West
Join The Reverend TJ for an unforgettable evening at Tiki House Key West. Known for his dynamic performances and engaging stage presence, The Reverend TJ…
Free
David Warren at The Bull & Whistle Bar
David Warren brings his dynamic musical talents to The Bull & Whistle Bar, a vibrant nightlife spot in Key West’s Old Town. Known for his…
Free
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…
Free
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…
Free
Trenton Chandler ~ Rick’s Bar Downstairs Stage
Catch Trenton Chandler, a talented country musician and songwriter from Shallowater, Texas, live on the Rick's Bar Downstairs Stage. Influenced by legends like Elvis and…
Free
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…
Free
Pierce August at Hank’s Hair of the Dog Saloon
Experience the captivating performance of Pierce August at Hank's Hair of the Dog Saloon, Key West's vibrant nightlife gem. Known for delivering unforgettable live music,…
Free
Aaron Hudgins ~ Rick’s Bar Downstairs Stage
Experience the captivating sounds of Aaron Hudgins at Rick's Bar Downstairs Stage, nestled in Key West's vibrant nightlife hub. Hudgins, a skilled musician, delivers an…
Free
Sandra Lee at The Bull & Whistle Bar
Experience the captivating sounds of musician Sandra Lee at The Bull & Whistle Bar. Nestled in Key West's vibrant Old Town, her soulful performances breathe…
Free
Cliff Cody at Hank’s Hair of the Dog Saloon
Cliff Cody, a captivating musician, graces Hank's Hair of the Dog Saloon in Key West with his soulful tunes and engaging performances. Known for his…
Free
LaurLea & Tripp Fabulous at Sloppy Joe’s Bar
Catch LaurLea & Tripp Fabulous, a dynamic party rock band from Philadelphia, lighting up the stage at Sloppy Joe's Bar with high-energy performances from 10:00…
Free