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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Featured
Key West
New Year's Eve Red Shoe Drop
Dec 31, 2025
Ring in the New Year, Key West-style, with one of the island’s most iconic and flamboyant celebrations — the Red Shoe Drop! As the clock counts down...
Featured
Key West
Key West Literary Seminar (2026)
Jan 8 - 11, 2026
The Key West Literary Seminar is a world-renowned annual event that celebrates the art of storytelling in one of the most inspiring literary...
Featured
Key West
Mile 0 Fest (2026)
Jan 27 - 31, 2026
Experience Mile 0 Fest in the stunning Florida Keys! Enjoy five days of top Texas Red Dirt & Americana music, beachfront parties, and unforgettable...
Key West
Key West Tropical Forest & Botanical Garden turns 90
Jan 30, 2026
Discover paradise at the Key West Tropical Forest & Botanical Garden! Explore lush trails, vibrant native plants, and unique wildlife in the heart of...
Key West
Petals and Pearls Gala
Jan 30, 2026
Celebrate the 90th Anniversary Gala at Key West Garden Club’s “Petals & Pearls” event! Enjoy an enchanting evening of live music, gourmet cuisine, and...
The Lower Keys
Annual Spanish Fly Music Festival
Feb 1, 2026
The 8th Annual Spanish Fly Music Festival is set for Sunday, February 1, 2026 at Boondocks Grille & Draft House on Ramrod Key! What started as a way...
Key West
Dorian Wind Quintet at Tennessee Williams Theater
Feb 1, 2026
\- Impromptu Classical Concerts - Recognized by critics, audiences, and colleagues alike for its polished and passionate performances, the Dorian Wind...
Key West
Robert Cuccioli at Tennessee Williams Theater
Feb 2, 2026
Robert Cuccioli is known by many for his critically acclaimed TONY nominated performance in Jekyll & Hyde, for which he also received the Drama Desk...
Key West
The Massacoustics at Key West Theater
Feb 4 - 5, 2026
The Massacoustics formed in 2000 with Andrew Thompson (guitar/vocals) and Matthew Thompson (drums/bass/vocals). They've performed their own brand of...
Key West
Vienna Boys’ Choir at Tennessee Williams Theater
Feb 5, 2026
The Vienna Boys Choir is one of the most famous choirs in the world, and one of the oldest. Boys have been singing at Vienna's Imperial Chapel since...
The Lower Keys
Cuda Bowl Fishing Tournament (2026)
Feb 5 - 7, 2026
Join us in the Florida Keys for the legendary Cuda Bowl! Experience world-class flats fishing as anglers compete to catch barracuda in a fun...
Islamorada
Beats on the Bay - Touch & Go at Founders Park
Feb 6, 2026
Experience Beats on the Bay in the Florida Keys! Enjoy live music, delicious food, and stunning waterfront views at this vibrant event. Perfect for...
Key West
RAMS HEAD PRESENTS: MARY GAUTHIER WITH SPECIAL GUEST JAIMEE HARRIS at Key West Theater
Feb 6, 2026
Celebrate 25 years of Drag Queens in Limousines with Grammy-nominated singer-songwriter Mary Gauthier, whose fearless storytelling and heartfelt...
Marathon
Sombrero Beach Run
Feb 7 - 9, 2026
Join us in the Florida Keys for the Sombrero Beach Run! Enjoy a scenic race along beautiful Sombrero Beach, with options for all fitness levels...
Key West
Tropical Luncheon & Garden Party
Feb 8, 2026
Experience the Tropical Luncheon at the Key West Museum of Art & History! Join us for an unforgettable afternoon of island flavors, fascinating tales...
Key West
New York Philharmonic String Quartet at Tennessee Williams Theater
Feb 10, 2026
Frank Huang, Concertmaster Qianqian Li, Principal Second Violin Cynthia Phelps, Principal Viola Carter Brey, Principal Cello The New York Philharmonic...
Key West
Scott Kirby- 35 Years of Songs & Stories w/ Mike Michaels at Key West Theater
Feb 12 - 13, 2026
Singer, songwriter, guitarist, storyteller, traveler and road warrior are all words that aptly describe Scott Kirby. Finishing songs while driving...
Key West
Presidential Families Weekend Forum
Feb 12 - 16, 2026
Join history enthusiasts and presidential descendants for Presidential Families Weekend from February 15-17, 2025, at Florida's only presidential site...
