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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Islamorada
Swim for Alligator Lighthouse
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Dive into an unforgettable adventure in the Florida Keys during the Alligator Lighthouse Swim, an exhilarating open-water challenge surrounded by...
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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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The Lower Keys
Sugarloaf Showdown
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November 12–14, 2026 | Lower Florida Keys Cast a line for competition, camaraderie, and a great cause at the 13th Annual LKGA Sugarloaf Showdown, a...
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Islamorada
Cheeca Lodge & Spa All-American Backcountry Tournament
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November 12–14, 2026 | Cheeca Lodge & Spa, Islamorada Experience two days of world-class sportfishing in the heart of the Florida Keys during the All...
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Key West
Destroying David – Waterfront Playhouse (Spotlight Series)
November 12-14, 2026 Destroying David at Waterfront Playhouse launches the Spotlight Series with a thought-provoking and immersive theatrical...
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Key West
A Tribute to the Songs of Pete & Wayne
Key West Theater | 512 Eaton Street, Key West Celebrate the songs, stories, and unmistakable humor of a beloved Key West duo with A Tribute to the...
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Key West
The Garcia Project
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
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...
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Tour de Keys Ride for a Cause
Saturday, November 21, 2026. Pedal through paradise for a purpose during Tour de Keys, a scenic charity cycling adventure that takes riders along the...
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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...
