7 events found.
Ongoing
Week of Events
DJ Marty ~ Red Garter Saloon at Rick’s Entertainment Complex
Experience the electrifying beats of DJ Marty at the Red Garter Saloon, part of Rick's Entertainment Complex in Key West. Known for his dynamic sets…
Free
DURTBAGS ~ Durty Harry’s Stage at Rick’s Entertainment Complex
Join The Durtbags, Key West's premier party rock band, for an electrifying experience at Durty Harry's Stage in Rick's Entertainment Complex. Performing live every Thursday…
Free
DJ Chaka ~ Rick’s Bar Upstairs at Rick’s Entertainment Complex
Experience the electrifying beats of DJ Chaka at Rick's Bar Upstairs in Rick's Entertainment Complex, Key West. As the powerhouse DJ of the night, Chaka…
Free
Karaoke w/ Jason ~ Rick’s Bar Downstairs at Rick’s Entertainment Complex
Join Jason for an unforgettable karaoke night at Rick's Bar, located in Rick's Entertainment Complex, Key West. As a standout entertainer, Jason energizes the crowd…
Free
DJ Marty ~ Red Garter Saloon at Rick’s Entertainment Complex
Join DJ Marty at the Red Garter Saloon in Rick's Entertainment Complex for an electrifying night of music and fun. Located in Old Town Key…
Free
DURTBAGS~ Durty Harry’s Stage at Rick’s Entertainment Complex
Join The Durtbags, Key West’s ultimate party rock band, every Thursday through Sunday at Durty Harry's Stage in Rick's Entertainment Complex. Experience their electrifying performances…
Free
DJ Kori ~ Rick’s Bar Upstairs at Rick’s Entertainment Complex
Experience an electrifying night with DJ Kori at Rick's Bar, located in Rick's Entertainment Complex, the heart of Old Town Key West. DJ Kori spins…
Free
Karaoke w/ Jason ~ Rick’s Bar Downstairs at Rick’s Entertainment Complex
Join Jason for an unforgettable karaoke night at Rick's Bar, located downstairs at Rick's Entertainment Complex. Known for his engaging and lively hosting style, Jason…
Free
DJ Marty ~ Red Garter Saloon at Rick’s Entertainment Complex
Immerse yourself in an unforgettable night with DJ Marty at the Red Garter Saloon in Rick's Entertainment Complex. Known for crafting electrifying playlists that keep…
Free
Monday Night Football at Rick’s Entertainment Complex
Join the excitement of Monday Night Football at Rick's Entertainment Complex in Old Town Key West. Amidst the vibrant nightlife, experience electrifying performances by talented…
Free
HYPER DRIVE ~ Durty Harry’s Stage at Rick’s Entertainment Complex
Experience the electrifying energy of Hyper Drive at Durty Harry's Stage in Rick's Entertainment Complex, Key West's nightlife epicenter. Known for their dynamic performances, this…
Free
DJ Duke ~ Rick’s Bar Upstairs at Rick’s Entertainment Complex
Experience an electrifying night with DJ Duke at Rick's Bar, located upstairs at Key West's iconic Rick's Entertainment Complex. Renowned for his dynamic sets and…
Free
Karaoke w/ Jorge ~ Rick’s Bar Downstairs at Rick’s Entertainment Complex
Join Jorge for an unforgettable karaoke night at Rick's Bar, located in the heart of Old Town Key West. Renowned for his charismatic stage presence…
Free
DJ Todd ~ Red Garter Saloon at Rick’s Entertainment Complex
Experience an unforgettable night with DJ Todd at the Red Garter Saloon, located within Rick's Entertainment Complex in Key West. Known for his electrifying sets…
Free
LUVBOM ~ Durty Harry’s Stage at Rick’s Entertainment Complex
LUVBOM will electrify Durty Harry's Stage at Rick's Entertainment Complex, located in lively Old Town Key West. As the heart of Key West nightlife, Rick's…
Free
DJ Duke ~ Rick’s Bar Upstairs at Rick’s Entertainment Complex
Experience an electrifying night with DJ Duke at Rick's Bar, located upstairs in Rick's Entertainment Complex. DJ Duke brings the beats to life in Key…
Free
Karaoke w/ Jorge ~ Rick’s Bar Downstairs at Rick’s Entertainment Complex
Join Jorge for an unforgettable karaoke experience at Rick's Bar, located in Rick's Entertainment Complex in Old Town Key West. As the heart and soul…
Free
DJ Todd ~ Red Garter Saloon at Rick’s Entertainment Complex
Experience an electrifying night with DJ Todd at the Red Garter Saloon, part of Rick's Entertainment Complex in Key West. Known for his dynamic sets…
Free
KRANK SINATRA~ Durty Harry’s Stage at Rick’s Entertainment Complex
Experience the electrifying performance of Krank Sinatra at Durty Harry's Stage, Rick's Entertainment Complex. Known for their dynamic stage presence and powerful sound, Krank Sinatra…
Free
DJ Duke ~ Rick’s Bar Upstairs at Rick’s Entertainment Complex
Experience an unforgettable night with DJ Duke at Rick's Bar, located upstairs at Rick's Entertainment Complex in Old Town Key West. Known for his vibrant…
Free
Karaoke w/ Davis ~ Rick’s Bar Downstairs at Rick’s Entertainment Complex
Join Davis for an unforgettable karaoke experience at Rick's Bar, nestled in the vibrant Rick's Entertainment Complex in Old Town Key West. Known for his…
Free
DJ Marty ~ Red Garter Saloon at Rick’s Entertainment Complex
Join DJ Marty at the Red Garter Saloon in Rick's Entertainment Complex, Key West's vibrant nightlife hub. Known for electrifying beats and dynamic mixes, DJ…
Free
DURTBAGS~ Durty Harry’s Stage at Rick’s Entertainment Complex
Experience the exhilarating energy of The Durtbags, Key West’s premier party rock band, at Durty Harry’s Stage in Rick's Entertainment Complex. Playing live every Thursday…
Free
DJ Chaka ~ Rick’s Bar Upstairs at Rick’s Entertainment Complex
Experience the electrifying beats of DJ Chaka at Rick's Bar Upstairs, located in Key West's renowned Rick's Entertainment Complex. Known for his dynamic mixes and…
Free
Karaoke w/ Jason ~ Rick’s Bar Downstairs at Rick’s Entertainment Complex
Join Jason for an unforgettable karaoke night at Rick's Bar, located downstairs at Rick's Entertainment Complex in Key West. Jason's charismatic hosting and dynamic energy…
Free
DJ Marty ~ Red Garter Saloon at Rick’s Entertainment Complex
Experience the electrifying beats of DJ Marty at the Red Garter Saloon, nestled within Rick's Entertainment Complex in Old Town Key West. Known for his…
Free
DURTBAGS ~ Durty Harry’s Stage at Rick’s Entertainment Complex
Experience the electrifying energy of The Durtbags, Key West's premier party rock band, at Durty Harry's Stage in Rick's Entertainment Complex. Performing Thursday through Sunday,…
Free
DJ Duke ~ Rick’s Bar Upstairs at Rick’s Entertainment Complex
Experience an electrifying night with DJ Duke at Rick's Bar, nestled in the vibrant Rick's Entertainment Complex. As Key West's premier DJ, Duke crafts unforgettable…
Free
Karaoke w/ Jason ~ Rick’s Bar Downstairs at Rick’s Entertainment Complex
Join the lively atmosphere of Rick's Bar at Rick's Entertainment Complex for an unforgettable night of karaoke with Jason. Known for his engaging stage presence,…
Free
Monday, January 26, 2026
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January 26, 2026 -Webb Dillard ~ Rick’s Bar Downstairs at Rick’s Entertainment Complex
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January 26, 2026 -Just George ~ Rick’s Bar Downstairs at Rick’s Entertainment Complex
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January 26, 2026 -Aaron Hudgins ~ Rick’s Bar Downstairs at Rick’s Entertainment Complex
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January 26, 2026 -Saltwater Saints at Sloppy Joe’s Bar
Webb Dillard ~ Rick’s Bar Downstairs at Rick’s Entertainment Complex
Experience the dynamic performances of musician Webb Dillard at Rick's Bar, nestled in Key West's vibrant entertainment scene. Renowned for captivating live music, Webb brings…
Free
Just George ~ Rick’s Bar Downstairs at Rick’s Entertainment Complex
Experience an unforgettable evening with Just George at Rick's Bar, located in the vibrant Rick's Entertainment Complex. As a talented musician, Just George captivates audiences…
Free
Aaron Hudgins ~ Rick’s Bar Downstairs at Rick’s Entertainment Complex
Experience the electrifying performance of musician Aaron Hudgins at Rick's Bar, nestled within Key West’s vibrant Rick's Entertainment Complex. Renowned for his dynamic presence and…
Free
Saltwater Saints at Sloppy Joe’s Bar
Saltwater Saints bring their electrifying performance to the iconic Sloppy Joe's Bar in Key West. Known for their energetic and captivating live shows, this talented…
Free
Tuesday, January 27, 2026
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January 27, 2026 -Shanty Hounds ~Rick’s Bar Downstairs at Rick’s Entertainment Complex
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January 27, 2026 -Jesse Lee ~Rick’s Bar Downstairs at Rick’s Entertainment Complex
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January 27, 2026 -Two in the Pink at Sloppy Joe’s Bar
Shanty Hounds ~Rick’s Bar Downstairs at Rick’s Entertainment Complex
Enjoy an unforgettable evening with the Shanty Hounds at Rick's Bar, nestled in the heart of Old Town Key West. This talented band delivers an…
Free
Jesse Lee ~Rick’s Bar Downstairs at Rick’s Entertainment Complex
Experience the electrifying performance of musician Jesse Lee at Rick's Bar, nestled within Key West's largest entertainment hub. Known for his captivating live music, Jesse…
Free
Two in the Pink at Sloppy Joe’s Bar
Experience the dynamic tunes of Two in the Pink at Sloppy Joe's Bar. This talented duo features Sid The Bayou Kid on guitar and vocals,…
Free
Wednesday, January 28, 2026
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January 28, 2026 -Brian Roberts at Sloppy Joe’s Bar
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January 28, 2026 -Harley Ray ~ Rick’s Bar Downstairs at Rick’s Entertainment Complex
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January 28, 2026 -Joe the Show ~ Rick’s Bar Downstairs at Rick’s Entertainment Complex
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January 28, 2026 -Comedy Key West Open Mic at Comedy Key West
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January 28, 2026Juliano Brothers at Sloppy Joe’s Bar
Brian Roberts at Sloppy Joe’s Bar
Experience the captivating melodies of Brian Roberts at Sloppy Joe's Bar, a historic Key West landmark. Renowned for its vibrant atmosphere, the bar comes alive…
Free
Harley Ray ~ Rick’s Bar Downstairs at Rick’s Entertainment Complex
Experience the electrifying performance of musician Harley Ray at Rick's Bar, located in the heart of Old Town Key West's vibrant nightlife scene. Known for…
Free
Joe the Show ~ Rick’s Bar Downstairs at Rick’s Entertainment Complex
Experience the electrifying performance of Joe the Show at Rick's Bar, nestled in the heart of Old Town Key West. Known for his captivating stage…
Free
Comedy Key West Open Mic at Comedy Key West
At Comedy Key West Open Mic, entertainers take the spotlight in a lively night of comedy, music, and variety acts. Hosted in the cozy Comedy…
Free
Juliano Brothers at Sloppy Joe’s Bar
The Juliano Brothers, a dynamic trio from West Deptford, NJ, are set to electrify Sloppy Joe's Bar with their vibrant live performance. Known for their…
Free
Thursday, January 29, 2026
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January 29, 2026 -Jeff Harris ~ Rick’s Bar Downstairs at Rick’s Entertainment Complex
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January 29, 2026 -Andrew B. ~ Rick’s Bar Downstairs at Rick’s Entertainment Complex
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January 29, 2026 -Jim Florentine at Comedy Key West
Jeff Harris ~ Rick’s Bar Downstairs at Rick’s Entertainment Complex
Join talented musician Jeff Harris at Rick's Bar, nestled within Rick's Entertainment Complex in Key West. Experience his captivating live performances in Florida's largest club…
Free
Andrew B. ~ Rick’s Bar Downstairs at Rick’s Entertainment Complex
Join musician Andrew B. at Rick's Bar Downstairs in Rick's Entertainment Complex for a captivating night of live music. Known for his dynamic performances, Andrew…
Free
Jim Florentine at Comedy Key West
Join us at Comedy Key West for a night of laughter with the legendary Jim Florentine. With a career spanning nearly 25 years, Florentine is…
$33
Friday, January 30, 2026
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January 30, 2026 -Tim Hollohan at Sloppy Joe’s Bar
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January 30, 2026 -Wynn Tayor ~ Rick’s Bar Downstairs Stage at Rick’s Entertainment Complex
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January 30, 2026 -Joe the Show ~ Rick’s Bar Downstairs Stage at Rick’s Entertainment Complex
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January 30, 2026 -DALLAS REMINGTON ~ Durty Harry’s Stage at Rick’s Entertainment Complex
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January 30, 2026 -Joe the Show ~ Rick’s Bar Downstairs at Rick’s Entertainment Complex
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January 30, 2026 -Jim Florentine at Comedy Key West
Tim Hollohan at Sloppy Joe’s Bar
At Sloppy Joe's Bar, Tim Hollohan captivates audiences with his vibrant stage presence and interactive performances. Originally from Columbia, South Carolina, Tim's dynamic musical talents…
Free
Wynn Tayor ~ Rick’s Bar Downstairs Stage at Rick’s Entertainment Complex
Experience the captivating performance of musician Wynn Taylor at Rick's Bar Downstairs Stage in Rick's Entertainment Complex. Known for his electrifying presence and musical prowess,…
Free
Joe the Show ~ Rick’s Bar Downstairs Stage at Rick’s Entertainment Complex
Experience the electrifying performance of Joe the Show at Rick's Bar Downstairs Stage in Key West's premier entertainment complex. Known for his dynamic musical talent,…
Free
DALLAS REMINGTON ~ Durty Harry’s Stage at Rick’s Entertainment Complex
Experience Dallas Remington live at Durty Harry's Stage in Rick's Entertainment Complex, Key West's iconic nightlife venue. Known for her captivating performances, Dallas brings a…
Free
Joe the Show ~ Rick’s Bar Downstairs at Rick’s Entertainment Complex
Enjoy an unforgettable night with Joe the Show at Rick's Bar, part of Key West's largest entertainment complex. Known for electrifying performances, Joe The Show…
Free
Jim Florentine at Comedy Key West
Join us at Comedy Key West for a night of laughter with Jim Florentine, a comedic powerhouse renowned for his 25-year career across multiple media…
$33
Saturday, January 31, 2026
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January 31, 2026 -Zack Seemiller ~ Rick’s Bar Downstairs Stage at Rick’s Entertainment Complex
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January 31, 2026 -Elle Haley ~ Rick’s Bar Downstairs Stage at Rick’s Entertainment Complex
Zack Seemiller ~ Rick’s Bar Downstairs Stage at Rick’s Entertainment Complex
Zack Seemiller, a charismatic musician known for his engaging performances, takes the stage at Rick's Bar Downstairs in Rick's Entertainment Complex. Located in Key West's…
Free
Elle Haley ~ Rick’s Bar Downstairs Stage at Rick’s Entertainment Complex
Experience an unforgettable night with the talented musician Elle Haley at Rick's Bar Downstairs Stage, part of Key West's iconic Rick's Entertainment Complex. As she…
Free
Sunday, February 1, 2026
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February 1, 2026 -801 Karaoke – Hosted by Jeff
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February 1, 2026 -Tea Dance at La Te Da
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