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
Fantasy Fest
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Each October, Fantasy Fest transforms Key West into a colorful celebration of costumes, creativity, music, and performance. The multi-day festival was...
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Key West
Key West Film Festival
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Sunday, November 15, 2026. Settle in for a soulful night of jams as The Garcia Project returns to the Key West Theater, presented by Rams Head...
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Key West
RAMS HEAD PRESENTS: Marty Stuart and His Fabulous Superlatives
Experience an unforgettable evening of country music as Marty Stuart and His Fabulous Superlatives take the stage at the Key West Theater. A five-time...
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Key West
RAMS HEAD PRESENTS: DUSTY SLAY THE NEIGHBORHOOD GUY TOUR
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Get ready for a good time when Dusty Slay brings his unmistakable Southern humor and laid-back storytelling to the stage. Raised on Lot 8 of a mobile...
Key West
Junk in the Trunk: Truman Waterfront Community Yard Sale
Saturday, November 21, 2026, from 8:00 a.m. to 1:00 p.m. Junk in the Trunk returns to Truman Waterfront Park for a straight ahead community yard sale...
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Key West
Rams Head Presents: Buena Vista Social Orchestra
Experience the timeless sounds of Cuba as the Buena Vista Orchestra takes the stage at the Key West Theater, bringing the rhythms and musical...
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Key West
Thanksgiving at Hot Tin Roof
Thursday, November 26, 2026. Celebrate Thanksgiving overlooking the water at Hot Tin Roof, the signature restaurant at Ocean Key Resort & Spa in Key...
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Key West
Thanksgiving Feast at Key West Cooking Show
Thursday, November 26, 2026, with seatings at 11 a.m. and 2 p.m. Celebrate Thanksgiving in Key West without spending the day in the kitchen during a...
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Key West
Thanksgiving Sunset Dinner Cruise
Thanksgiving Day, Thursday, November 26, 2026, departing at 5 p.m. Trade the traditional dining room for a Thanksgiving celebration on the water...
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Key West
Black Friday Market: Shopping Extravaganza
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Saturday, November 28, 2026, from 10 a.m. to 6 p.m. Shop local and celebrate the holiday season during the Black Friday Market: Shopping Extravaganza...
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Key West
It's A Wonderful Live: A Live Radio Play at Waterfront Playhouse
December 3-17, 2026 It’s a Wonderful Life: A Live Radio Play at Waterfront Playhouse brings a festive twist to the holiday season with a creative...
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 as Steven Dietz’s romantic comedy Shooting Star opens the Red...
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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
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...
