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
19 events found.
entertainment
Events for January 27, 2026
Ongoing
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
Collette Campbell at Sloppy Joe’s Bar
Collette Campbell, a talented musician, takes the stage at Sloppy Joe's Bar, captivating audiences with her dynamic performance from 10:00 am to 11:45 am. Renowned…
Free
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
Brian Roberts at Sloppy Joe’s Bar
Brian Roberts captivates audiences at Sloppy Joe's Bar with his dynamic musical performances. Surrounded by the vibrant atmosphere of this historic Key West landmark, Roberts…
Free
Oren Polak at Schooner Wharf Bar
Oren Polak enchants audiences at the iconic Schooner Wharf Bar with his captivating music. Set in Key West's historic seaport, this open-air venue features Polak's…
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
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…
Free
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…
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
Gary Hempsey at Schooner Wharf Bar
Gary Hempsey delivers captivating live performances at Schooner Wharf Bar in Key West. Known for his engaging stage presence and diverse musical repertoire, Hempsey enchants…
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
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
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
Saltwater Saints at Sloppy Joe’s Bar
Experience the vibrant energy of Saltwater Saints at the iconic Sloppy Joe's Bar in Key West. Known for their captivating performances, Saltwater Saints bring a…
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