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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Islamorada
Fall Backcountry Fly Championship
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Experience the beauty of the Florida Keys from the water during the Backcountry Fly Championship in Islamorada, a laid-back yet competitive fly...
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Key West
Key West Brewfest 2026
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Raise a glass and experience the spirited side of Key West during Key West Brewfest, a multi-day celebration of craft beer, culinary creativity, live...
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Key West
Key West oktoBREWfest
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Raise a glass to island-style Oktoberfest fun at Key West OktoberBREWfest, a lively tasting celebration at the Southernmost Beach Resort. Set against...
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The Lower Keys
Lower Keys Rotary Fall Festival/Haunted House
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Experience the festive side of the Florida Keys at the Lower Keys Rotary Fall Festival and Haunted House, a seasonal community celebration filled with...
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Marathon
America 250 Florida Keys: 7 Mile Bridge Sunset Celebration
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Event Time: 5:00–7:30 p.m. Sunset: 7:05 p.m. Celebrate America’s 250th birthday in true Florida Keys style during the 7 Mile Bridge Sunset Celebration...
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Key Largo
REEF Fest (2026)
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Experience REEF Fest in Key Largo, a celebration of marine conservation, ocean exploration, and the incredible underwater world of the Florida Keys...
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Key West
Hedwig and the Angry Inch at Waterfront Playhouse
October 15–23, 2026 Waterfront Playhouse launches its 88th season with the groundbreaking rock musical Hedwig and the Angry Inch, presented in an...
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Islamorada
Casting for Cats Backcountry Tournament
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October 16–17, 2026. Cast a line for a good cause during the annual Casting for Cats Backcountry Fishing Tournament, a longtime Upper Keys tradition...
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Islamorada
Ladies, Let’s Go Fishing!” Florida Keys Saltwater Seminar and Fishing Fever Inshore/Offshore Tournament
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October 16–18, 2026. Build confidence on the water during Ladies, Let’s Go Fishing!, a Florida Keys weekend designed to introduce and encourage women...
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Key West
Rams Head Presents: Garrison Keillor and Erica Rhodes – The Crazy Uncle and His Sensible Niece
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Tuesday, October 27, 2026, at 8:00 p.m. Enjoy an evening of storytelling and comedy as Garrison Keillor and Erica Rhodes bring The Crazy Uncle and His...
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Key West
Will Kimbrough Live at the Key West Theater
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Celebrate an evening of exceptional songwriting and musicianship with Will Kimbrough at the Key West Theater. An acclaimed singer-songwriter...
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Key West
Rams Head Presents: Buffett Through the Years
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Friday, October 30, 2026, 8:00 p.m (doors open at 7:00 p.m) Celebrate the music and legacy of Jimmy Buffett with Buffett Through the Years, featuring...
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Key West
Texas Trop Rock: Jerry Diaz, Dan Sullivan, Jonas Lorence Band
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Saturday, October 31, 2026, at 1:00 p.m. Doors open at 12:00 p.m. at the Key West Theater. Celebrate the sounds of the coast with Texas Trop Rock...
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Key West
Jim Morris Tribute
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Celebrate the life, music, and enduring legacy of beloved Southwest Florida singer-songwriter Jim Morris with a special tribute performance by the...
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Key West
Race World Offshore
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Sports fans with a need for speed can fuel their passion at the Race World Offshore Key West World Championship, set for Saturday through Saturday, in...
