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.
See Some Shenanigans
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Key West
Fantasy Fest
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Fantasy Fest is an electrifying, 10-day costume and performance festival held annually in Key West, Florida, each October. First launched in 1979 by...
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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, 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
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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Islamorada
Islamorada Junior Sailfish Tournament
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December 11–13, 2026. Celebrate more than six decades of youth sportfishing during the 61st Annual Islamorada Junior Sailfish Tournament, a Florida...
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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...
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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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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...
