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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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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Marathon
Hunter's Moon Full Moon Dinner at Little Palm Island
Monday, October 26, 2026, by reservation. Dine beneath the glow of the Hunter’s Moon during a special Full Moon Dinner at Little Palm Island Resort &...
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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 Largo
REEF Ocean After Hours - Spooky Fish Bingo & Costume Contest
Tuesday, October 27, 2026, at 6 p.m. Celebrate Halloween week with an underwater twist during Spooky Fish Bingo at the REEF Ocean Exploration Center...
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Marathon
Dolphin Research Center’s Dolphin Sunset Celebration
Experience a truly unforgettable evening at Dolphin Research Center in the Florida Keys with the Dolphin Sunset Celebration, an intimate once-a-month...
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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 Largo
Owl-O-Ween
Celebrate Halloween the wild way at Owl-O-Ween, a family-friendly evening presented by the Florida Keys Wild Bird Center at the Laura Quinn Wild Bird...
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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
Order of the Sleepless Knights Tour
October 28–November 1, 2026. Celebrate the music, stories, and Key West legacy of Jimmy Buffett during the Gathering of the Order of the Sleepless...
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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...
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Key West
Jim Morris Tribute
Celebrate the music and enduring legacy of beloved Southwest Florida singer-songwriter Jim Morris with a special tribute performance by the Tropicool...
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Key West
Race World Offshore
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Feel the need for speed at the Race World Offshore Key West World Championship, when the turquoise waters surrounding Key West become the setting for...
