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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Experience the thrill of the Alligator Lighthouse Swim in the stunning Florida Keys! Swim 8 miles in crystal-clear waters, enjoy vibrant marine life, and celebrate with fellow adventurers. Perfect for leisure travelers seeking excitement, natural beauty, and unforgettable memories.
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Key West
Fantasy Fest
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Fantasy Fest is Key West’s signature 10-day celebration of costumes, creativity, music, performance, and larger-than-life imagination, transforming...
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Key West
Just a Few Friends Key West
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Celebrate the music, memories, and island spirit of Jimmy Buffett during a four-day tribute in the place that helped inspire it all — Key West. This...
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Key West
Shrimp Boat Sound: Echoes from the Edge | Movie Panel Discussion
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Discover a fascinating chapter of Key West’s musical history with Shrimp Boat Sound: Echoes from the Edge, a special presentation hosted by the Key...
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Key West
First Fridays on Fleming
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Every first Friday of the month from 6 to 9 p.m., Fleming Street in Key West transforms into a lively celebration of island creativity, community, and...
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Key West
CFK Pentathlon Swim Meet & Key West Open Water Swim (2026)
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The Open Water Swims begin shortly after the start of The College of the Florida Keys Swim Around Key West at Higgs Beach. Swimmers will take on a...
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Marathon
Heroes Salute 5K Run/Walk
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Saturday, September 5, 2026, 7:00–8:30 a.m. Start your morning with purpose at the Heroes Salute 5K Run/Walk at Hawks Cay Resort, part of the resort’s...
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Key West
3rd Annual Parrots & Margaritas 5K Run/Walk
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Kick off Labor Day weekend with the 3rd Annual Parrots & Margaritas 5K Run/Walk in Key West, a festive island-style race combining fitness, fun, and a...
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Islamorada
Son del Mundo Hispanic Heritage Event
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Celebrate the rich traditions, flavors, music, and creativity of Hispanic culture at the Hispanic Heritage Celebration in the Florida Keys. This...
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Key Largo
Pennekamp Paddle Day
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Saturday, September 12, 2026, from 11:00 a.m. to 4:00 p.m. Grab a paddle and dive into a full day of family fun at John Pennekamp Coral Reef State...
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Islamorada
Herman Lucerne Memorial Backcountry Championship (2026)
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Celebrate one of Islamorada’s most respected fishing traditions at the Herman Lucerne Memorial Backcountry Championship, an annual tournament that...
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Marathon
Grassy Key Paddle Battle
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Experience a full week of water sports, wellness, and island adventure at Grassy Flats Resort & Beach Club in the Florida Keys, where paddling...
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Key West
Happy Hour with the Historian | Presidents in the Florida Keys: Power, Politics, and Retreat
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Thursday, September 17, 2026, 5:00–6:00 p.m. Explore the surprising history of presidential visits to the Florida Keys during Happy Hour with the...
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Key Largo
Take Stock In Children Backcountry Challenge (2026)
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Support a meaningful cause while enjoying some of the Florida Keys’ renowned backcountry fishing during the Take Stock in Children Backcountry...
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The Lower Keys
Lower Keys Fall Migration Mania Birding & Nature Adventure
Experience the beauty of fall migration in the Florida Keys during Fall Migration Mania at the Key West Tropical Forest & Botanical Garden, a special...
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Key Largo
Delicate Balance of Nature Lecture Series: Early History of Diving in the Florida Keys with Dr. Sally Bauer
From pioneering explorers to the rise of modern recreational diving, the Florida Keys have played a central role in underwater discovery. Join Dr...
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The Lower Keys
IGFA Permit Invitational
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September 29–October 2, 2026. Experience world-class flats fishing during the IGFA Permit Invitational, an exclusive, invitation-only tournament...
