Events
It's not just another day in paradise! You'll find doings and happenings up and down the Keys, nearly every day of the year. Check out the latest fun and frolic below.
Only-In-The-Keys Festivals & Events
There’s always something happening in the Florida Keys & Key West, from eclectic festivals focusing on the area’s colorful history, arts and notable cuisine to events that celebrate the Keys’ unique environment, underwater adventures and quirky ambiance.
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Key West
Mile 0 Fest
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Experience Mile 0 Fest in the stunning Florida Keys! Enjoy five days of top Texas Red Dirt & Americana music, beachfront parties, and unforgettable...
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Key West
Junk in the Trunk: Holiday Re-Gifting Sale
Saturday, December 5, 2026, from 8:00 a.m. to 1:00 p.m. Junk in the Trunk puts a holiday spin on its reuse and repurpose concept with the first of two...
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Key West
Rich Vos at Comedy Key West
Dec 3rd - Dec 6, 2026 Rich Vos has four specials on Comedy Central and over 100 television appearances. He has been seen on HBO, HBO Max, Netflix...
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Key West
Shooting Star
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December 8, 2026 through January 2, 2027. Settle in for a heartwarming night of theater at Key West's beloved Red Barn Theatre, where Steven Dietz's...
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Key West
Steven Rogers at Comedy Key West
Dec 7 - Dec 10, 2025 Steven Rogers is a stand-up comedian known for his unique blend of wit, vulnerability, and sharp observational humor. His comedic...
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Key West
Shaun Cassidy UNWRAPPED: Songs & Stories For The Holidays
Thursday, December 10, 2026. Get ready to unwrap the holidays Key West style! Grammy-nominated singer, actor, writer, and producer Shaun Cassidy...
Key West
Distinguished Speaker Series: The Florida Sponge War, Culture, Competition, and Conflict
Thursday, December 10, 2026, from 6:00 to 7:00 p.m. Dr. Rina Bousalis takes the Florida Sponge War to Williams Hall for the Key West Art & Historical...
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Key West
Personal Effects at Fringe Theater
Dec 9 - Dec 13, 2025 Experience the world premiere of Personal Effects by local playwright Chris Moore, running December 9–13. When the adult children...
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Key West
Holiday Concert & Bazaar
Celebrate the season at the annual Holiday Concert & Bazaar at the Key West Museum of Art & History. This festive community event brings together...
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Key West
18th Annual A Positive Step 5K Rudolph Red Nose Run
Saturday, December 12, 2026. Pull on your loudest holiday pajamas and head for the southern end of Duval Street, because the 18th annual A Positive...
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Key West
The Broken Hearts: A Tribute to Tom Petty & The Heartbreakers
Saturday, December 12, 2026. Get ready to feel like a Refugee and dance down to the Last DJ as The Broken Hearts bring their acclaimed tribute to Tom...
Key West
Southpoint Divers Holiday Morning Reef Dives
Wednesday, December 23, 2026, with four more departures on December 26, December 29, January 1 and January 4. Check-in is 8:00 a.m., the boat leaves...
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Key West
67th Annual Key West Home Tours
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December 29 to 30, 2026, January 22 to 23, 2027, February 12 to 13, 2027, and March 12 to 13, 2027, from 1:00 to 4:00 p.m. each day. Ever strolled...
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Key West
New Year's Eve Red Shoe Drop
Ring in the New Year, Key West-style, with one of the island’s most iconic and flamboyant celebrations — the Red Shoe Drop! As the clock counts down...
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Key West
The Restless Natives: Macon, Georgia's tribute to The Allman Brothers Band
Celebrate the music and legacy of The Allman Brothers Band with The Restless Natives, a Macon, Georgia-based tribute band dedicated to recreating the...
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Key West
Ben Harrison in Concert
Tuesday, January 5, 2027, with six more performances through April. Key West singer-songwriter, storyteller and longtime entertainer Ben Harrison...
