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...
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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
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
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
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)
Archives aren’t just for historians—in this engaging, lecture-style workshop, filmmaker and producer Monica Berra explores how archival research can...
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Key West
Rum Fest: Cliff Cody & Sharese
**Friday, August 14, 2026 — doors 7:00 pm, concert 8:00–10:00 pm.** Raise a glass and get ready to groove! As part of Key West Rum Fest, the Key West...
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Key West
Jesse Rice
**Saturday, August 15, 2026.** Get ready for a night of great live music at the Key West Theater with Jesse Rice! Part of Key West Rum Fest weekend...
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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 Largo
Key Largo Triathlon (2026)
Starting at sunrise, the event features a scenic open-water swim at Cannon Beach, a bike course along the Overseas Highway, and a run through a...
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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
This one-day tournament targets dolphin fish and is open to bartenders and restaurant employees. Kick-off and weigh-in events are to be held at the...
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Key West
Film Night: Wizard of Oz with Pink Floyd
**Full Description:** **August 18, 2026.** Experience the legendary "Dark Side of the Rainbow"! Catch the famous _Wizard of Oz_ film synced live to...
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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...
