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.
See Some Shenanigans
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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
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September 2 & 3, 2026 Singer-songwriters John Frinzi and Aaron Scherz bring their signature blend of tropical Americana, folk, country, and beach...
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Key West
Dave Landau at Comedy Key West
September 2–5, 2026 | 8:30 p.m. | Comedy Key West Get ready for four nights of sharp wit and big laughs as Dave Landau returns to Comedy Key West...
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Key West
Just a Few Friends Key West
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Celebrate the music, memories, and unmistakable island spirit of Jimmy Buffett during a four-day tribute in Key West, the island that played such an...
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Key West
Shrimp Boat Sound: Echoes from the Edge | Movie Panel Discussion
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Discover the stories behind one of Key West’s most influential recording studios during Shrimp Boat Sound: Echoes from the Edge, a special...
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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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Dive into the clear, warm waters of Key West during the Open Water Swims at Higgs Beach, held following the start of The College of the Florida Keys...
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Key West
3rd Annual Parrots & Margaritas 5K Run/Walk
Labor Day Weekend | 8 A.M. | Key West Kick off Labor Day weekend with a little exercise and a lot of island spirit at the 3rd Annual Parrots &...
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Key West
Occupational Hazard: The First Coral Reefers
Step into the creative heart of Old Town for Occupational Hazard: The First Coral Reefers, a special two-show engagement at the Key West Theater on...
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Key West
Happy Hour with the Historian | Presidents in the Florida Keys: Power, Politics, and Retreat
Discover the surprising presidential history of the Florida Keys during this installment of the Key West Art & Historical Society’s Happy Hour with...
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Key West
Walk on White
Stroll, sip, and celebrate creativity at Walk on White, Key West's beloved monthly art walk along the vibrant White Street arts district! On September...
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Key West
Gov't Mule & Ziggy Marley: Dreaming The Same Dream Tour
Wednesday, September 30, 2026 | Coffee Butler Amphitheater, Key West Get ready for an extraordinary night of music under the Key West sky as Gov’t...
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Key West
Surfrider Foundation Florida Keys Cleanups & Water Quality Monitoring
Join the effort to protect the ocean, beaches, and coastal habitats of the Florida Keys by volunteering with the Surfrider Foundation’s Florida Keys...
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Key West
Team OCEAN Boater Education & Stewardship Volunteers
Become an on-the-water ambassador for the Florida Keys by volunteering with Team OCEAN, a stewardship program of NOAA’s Florida Keys National Marine...
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Key West
Key West oktoBREWfest
Raise a glass and celebrate the season, island style, at Key West OktoberBREWfest, a lively tasting event at the Southernmost Beach Resort. Beer...
Key West
Womankind Greene Street Fundraiser
Join the Key West community for a special fundraiser on Greene Street benefiting Womankind, the island's beloved nonprofit health center dedicated to...
