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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Islamorada
Fish With A Hero Islamorada: Heroes' Welcome & Reception
Tuesday, September 15, 2026 | 6–8 p.m. | Islamorada Come together for a heartfelt evening of gratitude and community as Islamorada welcomes 25 wounded...
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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
Bruce Cockburn & Livingston Taylor at Key West Theater
Experience an exceptional evening of songs, stories, and masterful musicianship as acclaimed singer-songwriters Bruce Cockburn and Livingston Taylor...
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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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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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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...
