Name: Jordan Rock at Comedy Key West
Start: 2026-01-25T20:00:00-05:00
End: 2026-01-25T22:00:00-05:00

January 2026
Chris Thomas at Sloppy Joe’s Bar

January 25 @ 10:00 am - 11:45 am

Catch the captivating Chris Thomas live at Sloppy Joe's Bar, a historic Key West gem since 1937. Known for his dynamic performances, Chris brings an…

Free
John LaMere at Sloppy Joe’s Bar

January 25 @ 12:00 pm - 4:45 pm

John LaMere, a staple at Sloppy Joe's Bar since 2011, captivates audiences with his extensive and diverse song list, making every performance unforgettable. Known for…

Free
Gary Hempsey at Schooner Wharf Bar

January 25 @ 12:00 pm - 5:00 pm

Gary Hempsey captivates audiences at the Schooner Wharf Bar with his musical talents, delivering an unforgettable performance in Key West's laid-back, open-air setting. Surrounded by…

Free
Tea Dance at La Te Da

January 25 @ 4:00 pm - 6:00 pm

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 at Rick’s Entertainment Complex

January 25 @ 4:00 pm - 8:00 pm

Experience the soulful melodies of Trenton Chandler, a talented country musician from Shallowater, Texas, as he takes the stage at Rick's Bar in Key West.…

Free
801 Karaoke – Hosted by Jeff

January 25 @ 4:00 pm - 9:00 pm

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
Sunset Celebration at Mallory Square

January 25 @ 5:00 pm - 9:00 pm

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
Mojito at Sloppy Joe’s Bar

January 25 @ 5:30 pm - 9:30 pm

Experience the electrifying sounds of Mojito at Sloppy Joe's Bar, where their upbeat Latin rhythms will have you dancing all night long. This historic Key…

Free
Chris Kasper Duo at Schooner Wharf Bar

January 25 @ 6:30 pm - 10:30 pm

Enjoy an unforgettable performance by the Chris Kasper Duo at the Schooner Wharf Bar, a beloved waterfront venue in Key West. Known for their captivating…

Free
80s & 90s Trivia Night

January 25 @ 7:00 pm - 10:00 pm

Join 80s & 90s Trivia Night at The Retro Room in Old Town, Key West, where an engaging entertainer takes you on a nostalgic journey.…

Free
DJ Marty ~ Red Garter Saloon at Rick’s Entertainment Complex

January 25 @ 7:00 pm - January 26 @ 4:00 am

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
Jordan Rock at Comedy Key West

January 25 @ 8:00 pm - 10:00 pm

Join us at Comedy Key West for an unforgettable night with Jordan Rock, renowned for his roles in Netflix's LOVE and HBO Max's LOVE LIFE.…

$30

January 2026