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
Burgers & Buffet Tunes: A Tribute Show at Comedy Key West
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There are plenty of places to enjoy lunch in Key West, but only one invites you to dine with a legend. Burgers & Buffett Tunes at Comedy Key West is a...
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Key West
Hemingway in a Funny Way at Comedy Key West
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Raise a glass to one of Key West’s most legendary literary figures during this playful tribute to Ernest Hemingway at Comedy Key West. Led by comedian...
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Key West
Arts & Drafts
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Get creative midweek with Arts & Drafts at The Retro Room in Key West, held every Wednesday from 7 to 9 p.m. This relaxed, social art night pairs a...
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Key West
Prime of Life Yoga
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Reconnect with your body, mind, and the natural beauty of Key West during Prime of Life Yoga at the Key West Tropical Forest & Botanical Garden. Held...
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Key West
Key West Farmers Market
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Discover the vibrant Florida Keys Farmers Market, where fresh local flavors, handmade treasures, and island charm come together in a lively open-air...
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Key West
Eeland Stribling at Comedy Key West
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August 13–15, 2026, at 8:00 p.m. Comedy comes to the Florida Keys as Eeland Stribling takes the stage at Comedy Key West for three nights of stand-up...
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Key West
The Art and Impact of Archival Research with Monica Berra (PEAR)
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Discover how the past can become a powerful source of creative inspiration in this engaging, lecture-style workshop led by filmmaker and producer...
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Key West
Rum Fest: Cliff Cody & Sharese
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Friday, August 14, 2026 | Key West Theater Doors open at 7 p.m. | Concert 8–10 p.m. Raise a glass and get ready to groove! As part of Key West Rum...
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The Lower Keys
Open Air Market at Boondocks
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Every Saturday from 9 a.m. to 2 p.m., Boondocks Open-Air Market brings island flavor, local creativity, and tropical charm to Mile Marker 27.5 on...
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Key West
Jesse Rice
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Saturday, August 15, 2026 | Key West Theater Get ready for a night of great live music as Jesse Rice takes the stage at the Key West Theater during...
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Key Largo
Key Largo Triathlon (2026)
A True Florida Keys Race Experience Starting at sunrise, athletes will take on a scenic multisport challenge surrounded by the natural beauty and laid...
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Islamorada
Florida Keys Farmers Market
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Spend your Sunday soaking up local flavor at the Florida Keys Farmers Market in Islamorada. Held every Sunday from 10 a.m. to 3 p.m. in the parking...
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Key West
Glow Hours at Hugh’s Views
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Every Monday and Tuesday, experience Glow Hours at Hugh’s View in Key West, a one-of-a-kind rooftop evening set above The Studios of Key West. Take in...
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Key West
Monday Night Jazz Jams
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Kick off the week with the smooth sounds of Monday Night Jazz Jams at the William Weech American Legion Post 168 in Key West. Held every Monday from 8...
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Marathon
Bartenders Dolphin Tournament
Join the fun in the Middle Keys for this one-day dolphin fish tournament designed especially for bartenders and restaurant employees. This spirited...
