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...
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
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...
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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 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...
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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...
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...
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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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...
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Key West
Sheriff’s Animal Farm Open House
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Enjoy a fun and memorable family outing at the Monroe County Sheriff’s Animal Farm on Stock Island. Open the second and fourth Sunday of each month...
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Key West
Rams Head Presents: Garrison Keillor and Erica Rhodes – The Crazy Uncle and His Sensible Niece
Settle in for an evening of storytelling, laughter, and quick-witted comedy as Garrison Keillor and Erica Rhodes take the stage for The Crazy Uncle...
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Key West
Sunny Jim: Cayman Days
Settle into the intimate Back Stage Listening Room at the Key West Theater for an evening of island music and storytelling with Sunny Jim: Cayman Days...
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Key West
Rams Head Presents: Buffett Through the Years
Celebrate the music, stories, and island spirit of Jimmy Buffett with Buffett Through the Years, a live tribute show at the Key West Theater featuring...
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Key West
Sunny Jim: Florida Days
Settle into the intimate Back Stage Listening Room at the Key West Theater for Sunny Jim: Florida Days on October 30, an evening of island-inspired...
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Key West
Will Kimbrough Live at the Key West Theater
Experience an intimate evening of exceptional songwriting and musicianship as Will Kimbrough takes the stage at the Key West Theater. A respected...
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Key West
Texas Trop Rock: Jerry Diaz, Dan Sullivan, Jonas Lorence Band
Get ready for a night of coastal sounds and laid-back energy as Texas Trop Rock brings Jerry Diaz, Dan Sullivan, and the Jonas Lorence Band together...
