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
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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The Lower Keys
40th Annual Island Art Fair
Celebrate creativity and community at the Island Art Festival, a free, family-friendly gathering hosted by the Lower Keys Chamber of Commerce on Big...
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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...
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Islamorada
Islamorada Sailfish Tournament
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December 4–6, 2026. Experience one of the Florida Keys’ longstanding sportfishing traditions during the Islamorada Sailfish Tournament, the opening...
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...
Islamorada
Lignumvitae Christmas
Saturday, December 5, 2026. Christmas in the Keys arrives by boat. Lignumvitae Christmas takes over Lignumvitae Key Botanical State Park, a preserved...
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Marathon
7 Mile SantaCon
Celebrate the holidays Florida Keys style during the 2026 7 Mile SantaCon in Marathon. Break out your best Santa suit, elf attire, reindeer antlers...
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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...
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Key West
Shaun Cassidy UNWRAPPED: Songs & Stories For The Holidays
Thursday, December 10, 2026, at 8 p.m. Celebrate the season with Shaun Cassidy as he brings his new holiday show, UNWRAPPED: Songs & Stories For The...
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Key West
Holiday Concert & Bazaar
Friday, December 11, 2026, from 5 to 8 p.m. Celebrate the season during the Annual Holiday Concert & Bazaar at the Key West Museum of Art & History at...
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Islamorada
A Night in Monaco: Black & White Formal Gala Casino Night
Friday, December 11, 2026, from 6 to 10 p.m. Dress in your finest black and white attire for A Night in Monaco, a formal gala and casino night hosted...
