Name: Bradd Shadduck ~ Rick’s Bar Downstairs at Rick’s Entertainment Complex
Start: 2026-01-25T20:00:00-05:00
End: 2026-01-25T23:59:00-05:00

January 2026
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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

Categories:
Concert Happy Hour Live Music Music Nightlife
Tags:
entertainment happy hour island cuisine laid back atmosphere Live Music Musician open air raw bar seafood Waterfront
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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

Categories:
Arts & Performance Club Night Dance Performance Drag Show Live Entertainment Nightlife Party
Tags:
Attractions Bars cabaret shows drag performances hotels impersonations landmarks Live Entertainment live music venues nightlife over-21s only Restaurants tea dance theaters
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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

Categories:
Club Night Concert Live Music Music Nightlife
Tags:
Country Music Dancing entertainment Karaoke live music venues Live Shows Nashville Performer nightlife rock bands Songwriter
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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

Categories:
Karaoke LGBT Friendly Nightlife Nightlife & Social Party
Tags:
Cabaret Drag Shows entertainment Gay Bar Karaoke LGBT Friendly nightlife
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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

Categories:
Arts & Performance Live Music Outdoor Adventure Street Fair
Tags:
Attractions entertainment food vendors historic waterfront Live Music local artists public spaces street performers sunset celebration Waterfront
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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

Categories:
Cocktail Event Concert Live Music Music Nightlife Party
Tags:
American Cuisine Cocktails Dance Party Latin Music Live Entertainment Lively Atmosphere People Watching Rhythm Upbeat Music
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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

Categories:
Concert Food & Drink Live Music Music Nightlife
Tags:
entertainment Food Drink happy hour island cuisine laid back Live Music Local atmosphere open air raw bar seafood Waterfront
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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

Categories:
Game Night Games & Interactive Interactive Experience Theme Night Trivia
Tags:
Arcade Games Board Games Craft Beer Fun Atmosphere Interactive Experiences Nostalgic Experience Trivia Night
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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

Categories:
Club Night DJ Electronic Nightlife Nightlife & Social Party
Tags:
Bars Dance Club DJ entertainment Fun Karaoke Live Music nightlife People Watching
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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

Categories:
Arts & Performance Comedy Live Entertainment Nightlife
Tags:
comedy club comedy show entertainment & nightlife HBO Max Live Entertainment live music venues Netflix series open mic stand-up comedy
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Magic Of Frank Everhart at Schooner Wharf Bar

January 25 @ 8:00 pm - 11:59 pm

Experience the mesmerizing Magic of Frank Everhart at the iconic Schooner Wharf Bar. Renowned magician Frank Everhart captivates audiences with his spellbinding performances, creating magical…

Free

Categories:
Arts & Performance Entertainment Happy Hour Magic Show Nightlife
Tags:
entertainment happy hour island cuisine Live Music Magician open air seafood Waterfront
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Bradd Shadduck ~ Rick’s Bar Downstairs at Rick’s Entertainment Complex

January 25 @ 8:00 pm - 11:59 pm

Experience an unforgettable night with Bradd Shadduck at Rick's Bar in Key West's premier entertainment complex. A talented musician, Shadduck captivates audiences with his dynamic…

Free

Categories:
Club Night Concert Live Music Music Nightlife
Tags:
Bars Dance Club entertainment Fun Karaoke Live Music Musician nightlife People Watching

January 2026