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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Key West
Fantasy Fest
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Each October, Fantasy Fest transforms Key West into a colorful celebration of costumes, creativity, music, and performance. The multi-day festival was...
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Islamorada
The Hoy Shanty Crew Sing-Along
Saturday, October 17, 2026, from 6 to 8 p.m. Raise your voice and discover the musical traditions of life at sea during the first-ever Hoy Shanty Crew...
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Marathon
Children's Tours & Concert Series at Crane Point Museum & nature Center
Select dates throughout 2027: January 11 and 25; February 8 and 22; March 22; April 8, 13, 15 and 29; May 20; June 14 and 28; July 12; August 23; and...
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Islamorada
Mote Marine Laboratory Trivia Night at Florida Keys Brewing Company
Monday, October 19, 2026, from 7:30 to 9:30 p.m. Grab a drink, gather your smartest friends, and put your marine knowledge to the test during Mote...
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Islamorada
Cortadito: A Tribute to the Buena Vista Social Club
Monday, October 19, 2026, at 6 p.m. Experience the rhythms of traditional Cuban music when Cortadito brings its tribute to the legendary Buena Vista...
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Key West
The Greatest Hits Pool Party
Tuesday, October 20, 2026, from noon to 4 p.m. Dress like an icon and sing like a legend during the Greatest Hits Pool Party at Winslow’s Bungalows...
Key West
TUTU SALSA SESSIONS
Tuesday, October 20, 2026. Tutu Tuesday is one of Fantasy Fest's longest running traditions, and Southernmost Beach Café marks it with a day of drink...
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Key West
Rum Revelations: A Cocktail Adventure
Available on select dates October 20–24 and October 27–31, 2026. Mix, shake, and sip your way through the world of rum during Rum Revelations: A...
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Key Largo
REEF Ocean After Hours - Waterlust Trivia #1
Tuesday, October 20, 2026, at 6 p.m. Put your marine science knowledge to the test during the Waterlust Trivia Challenge at the REEF Ocean Exploration...
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Key West
Key West History Through Five Craft Cocktails
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Available October 20–24 and October 27–31, 2026, from 5 to 7 p.m. Raise a glass to Key West’s colorful past during Key West History Through Craft...
Key West
Heels For All with Paula Ali
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Wednesday, October 21 and Thursday, October 22, 2026, 1:00 to 2:30 PM both days. Step into a pair of heels and discover how balance, posture and even...
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Key West
LUV2GLOW: Liquid Frequency
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Get ready to light up the night at LUV2GLOW: Liquid Frequency, a two-night electronic and dance music experience taking over Rick’s Key West on...
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Marathon
Marathon Yacht Club Game Day Fundraiser
Wednesday, October 21, 2026, beginning at 11 a.m. Gather around the tables for a day of friendly competition at the Marathon Yacht Club, all while...
Key West
Photography Masterclass with Frank Stewart
Friday, October 23, 2026 from 1:00 to 3:30 PM. Bring your portfolio for in-depth critique from photographer Frank Stewart, in the Heinen Design Lab at...
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Islamorada
Treasure Treat Night
Available on select dates October 20–24 and October 27–31, 2026. Mix, shake, and sip your way through the world of rum during Rum Revelations: A...
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Key West
Screaming Green Halloween
Saturday, October 24, 2026, from 10 a.m. to 2 p.m. Celebrate Halloween with a green twist during Screaming Green Halloween at the Key West Tropical...
