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
Gov't Mule & Ziggy Marley: Dreaming The Same Dream Tour
**Wednesday, September 30, 2026.** Get ready for a once-in-a-lifetime night of music as two legends share one stage at Key West's Coffee Butler...
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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
John Frinzi & Aaron Scherz Live at Key West Theater
September 2 & 3, 2026 Singer-songwriters John Frinzi and Aaron Scherz bring their signature blend of tropical Americana, folk, country, and beach...
Key West
Dave Landau at Comedy Key West
September 2–5, 2026 | 8:30 p.m. Dave Landau returns to Comedy Key West for four nights of stand-up comedy. Known for his laid-back delivery and sharp...
Key West
Just a Few Friends Key West
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Celebrate the island spirit at the four-day tribute to Jimmy Buffett’s legacy in Key West, where it all began. This lively event features live music...
Key West
Just a Few Friends Festival
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Escape to the Florida Keys with Just a Few Friends Key West! Enjoy exclusive events, vibrant nightlife, and unforgettable experiences in paradise...
Key West
Shrimp Boat Sound: Echoes from the Edge | Movie Panel Discussion
Join the Key West Art & Historical Society for Shrimp Boat Sound: Echoes from the Edge, a special presentation exploring the history and legacy of one...
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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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Marathon
Heroes Salute 5K Run/Walk
Saturday, September 5, 2026, 7:00–8:30 a.m. Lace up and salute the heroes! Hawks Cay Resort kicks off its 18th Annual Heroes Salute Weekend with the...
Key West
3rd Annual Parrots & Margaritas 5K Run/Walk
Kick off Labor Day weekend with the 3rd Annual Parrots & Margaritas 5K Run/Walk in Key West. Beginning at 8 a.m., participants can run or walk a 5K...
Key West
CFK Pentathlon Swim Meet & Key West Open Water Swim (2026)
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The Open Water Swims take place following the start of The College of the Florida Keys Swim Around Key West at Higgs Beach. Participants will swim a...
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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...
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Key Largo
Pennekamp Paddle Day
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...
Islamorada
Son del Mundo Hispanic Heritage Event
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Experience vibrant music, dance, and art at the Hispanic Heritage Celebration in the Florida Keys! Enjoy live performances, delicious cuisine, and...
Key West
Happy Hour with the Historian | Presidents in the Florida Keys: Power, Politics, and Retreat
Explore the surprising history of presidential visits to the Florida Keys during this installment of the Key West Art & Historical Society’s Happy...
Marathon
Grassy Key Paddle Battle
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Join us for an unforgettable week of water sports, wellness, and island adventure at Grassy Flats Resort & Beach Club in the Florida Keys! The event...
Herman Lucerne Memorial Backcountry Championship (2026)
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The annual Herman Lucerne Memorial Backcountry Championship returns to Islamorada. During the one-of-a-kind event, participating anglers can spread...
