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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Dive into an unforgettable adventure in the Florida Keys during the Alligator Lighthouse Swim, an exhilarating open-water challenge surrounded by...
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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
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 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
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
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
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
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...
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Key West
Killer Prom: A Tubular Interactive Murder Mystery Comedy
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Step back into the ’80s for a totally tubular night of mystery, comedy, and audience participation when Gold Murder Presents Killer Prom: A Tubular...
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Key West
Rams Head Presents: The Ocean Blue
Step back into the shimmering sounds of alternative rock and indie pop as The Ocean Blue brings decades of melodic songwriting and fan favorites to...
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Key West
Bruce Cockburn & Livingston Taylor at Key West Theater
Experience an exceptional evening of songs, stories, and masterful musicianship as acclaimed singer-songwriters Bruce Cockburn and Livingston Taylor...
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Key West
Destroying David – Waterfront Playhouse (Spotlight Series)
November 12-14, 2026 Destroying David at Waterfront Playhouse launches the Spotlight Series with a thought-provoking and immersive theatrical...
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The Lower Keys
Sugarloaf Showdown
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November 12–14, 2026 | Lower Florida Keys Cast a line for competition, camaraderie, and a great cause at the 13th Annual LKGA Sugarloaf Showdown, a...
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Islamorada
Cheeca Lodge & Spa All-American Backcountry Tournament
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November 12–14, 2026 | Cheeca Lodge & Spa, Islamorada Experience two days of world-class sportfishing in the heart of the Florida Keys during the All...
Key West
Key West Oyster Fest
Join the inaugural Key West Oyster Fest on November 14 at the Historic Seaport! In front of Half Shell Raw Bar, savor Florida oysters and fresh...
