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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Featured
Key West
Race World Offshore (2025)
Nov 2 - 9, 2025
Sports fans with a need for speed can fuel their passion at the Race World Offshore Key West World Championship, set for Sunday through Sunday, Nov. 2...
Featured
Key West
Key West Film Festival
Nov 12 - 16, 2025
Key West Film Festival transforms the island into a vibrant destination for film lovers, filmmakers, and critics from around the world. Set against...
Key West
Rams Head Presents: The Broken Hearts: A Tribute to Tom Petty & The Heartbreakers
Nov 29, 2025
The Broken Hearts were created by former Tom Petty and Mudcrutch band mate; musician/songwriter/author/bassist/vocalist Charlie Souza, along with...
Key West
2025 Key West Holiday Fest
Dec 1 - 24, 2025
Experience the magic of Key West Holiday Fest! Enjoy festive lights, parades, historic inn tours, holiday markets, and unique island celebrations...
Key West
92nd Key West End of Prohibition Celebration
Dec 3 - 5, 2025
Celebrate the end of Prohibition, the 1920-1933 U.S. ban on alcohol, at this rollicking festival that also celebrates the birth of Sloppy Joe’s Bar...
Key West
Silk Dye Collage: Transfer Technique with Marianne Vogel
Dec 3, 2025
Discover your creative side in the Florida Keys! Join artist Marianne Vogel for a hands-on Silk Dye & Collage Transfer Technique workshop at The...
Key West
Rich Vos - Comedy
Dec 3 - 6, 2025
Rich Vos has four specials on Comedy Central and over 100 television appearances. He has been seen on HBO, HBO Max, Netflix, Showtime, and Starz. Rich...
Marathon
Downwindapalooza
Dec 4 - 13, 2025
Join Downwindapalooza in the Florida Keys for an unforgettable water adventure! Enjoy paddleboarding, kayaking, live music, local food, and a vibrant...
Key West
Mac McAnally
Dec 4 - 6, 2025
Record setting 10x CMA Musician of the Year, Mac McAnally is a Nashville Songwriters HoF, Mississippi Musicians HoF and Alabama Music HoF inductee...
Key West
Wet-Felted Fiber Vessels with Marianne Vogel
Dec 5, 2025
Discover the art of wet-felted fiber vessels with Marianne Vogel in the beautiful Florida Keys! Join this hands-on workshop to craft unique, colorful...
Key West
Shadow & Light: Exploring Contrast and Vision at the Island’s Edge - Exhibit Opening Reception
Dec 5, 2025
Exhibit Runs December 3, 2025 - February 15, 2026 The Key West Art & Historical Society will host its bi-annual juried exhibition Shadow & Light...
Key West
Holiday Fest-Inn Tours
Dec 5, 2025
Experience the magic of the Florida Keys at the Holiday Fest! Enjoy festive lights, live music, delicious food, and family-friendly activities in a...
Islamorada
2025 Islamorada Sailfish Tournament
Dec 5 - 8, 2025
The first leg of the Florida Keys Gold Cup Championship trifecta is the only tournament in the series to offer a junior division for anglers age 16...
Key West
Cello Stories: A Life Under Broadway
Dec 5, 2025
With twenty years of Broadway experience, and having performed as a regular member of twenty broadway shows, Mairi explores what it is to be a...
Islamorada
21st Annual Islamorada Holiday Fest
Dec 5, 2025
The forecast calls for lots of snow during the 21st Annual Islamorada Chamber of Commerce Holiday Fest, set for Friday December 5, 2025, from 4-10pm...
Key West
Wesley House Holiday Village & Bike Ride
Dec 5, 2025
Experience the magic of BeLighted 2025 in the Florida Keys! Join us for a dazzling evening of illuminated art, live entertainment, and community...
