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.
See Some Shenanigans
New Year's Eve Red Shoe Drop
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...
Key West Literary Seminar (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...
Mile 0 Fest (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 Tropical Forest & Botanical Garden turns 90
Discover paradise at the Key West Tropical Forest & Botanical Garden! Explore lush trails, vibrant native plants, and unique wildlife in the heart of...
Petals and Pearls Gala
Celebrate the 90th Anniversary Gala at Key West Garden Club’s “Petals & Pearls” event! Enjoy an enchanting evening of live music, gourmet cuisine, and...
Annual Spanish Fly Music Festival
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...
Dorian Wind Quintet at Tennessee Williams Theater
\- Impromptu Classical Concerts - Recognized by critics, audiences, and colleagues alike for its polished and passionate performances, the Dorian Wind...
Robert Cuccioli at Tennessee Williams Theater
Robert Cuccioli is known by many for his critically acclaimed TONY nominated performance in Jekyll & Hyde, for which he also received the Drama Desk...
The Massacoustics at Key West Theater
The Massacoustics formed in 2000 with Andrew Thompson (guitar/vocals) and Matthew Thompson (drums/bass/vocals). They've performed their own brand of...
Vienna Boys’ Choir at Tennessee Williams Theater
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...
Cuda Bowl Fishing Tournament (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...
Beats on the Bay - Touch & Go at Founders Park
Experience Beats on the Bay in the Florida Keys! Enjoy live music, delicious food, and stunning waterfront views at this vibrant event. Perfect for...
RAMS HEAD PRESENTS: MARY GAUTHIER WITH SPECIAL GUEST JAIMEE HARRIS at Key West Theater
Celebrate 25 years of Drag Queens in Limousines with Grammy-nominated singer-songwriter Mary Gauthier, whose fearless storytelling and heartfelt...
Sombrero Beach Run
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...
Tropical Luncheon & Garden Party
Experience the Tropical Luncheon at the Key West Museum of Art & History! Join us for an unforgettable afternoon of island flavors, fascinating tales...
New York Philharmonic String Quartet at Tennessee Williams Theater
Frank Huang, Concertmaster Qianqian Li, Principal Second Violin Cynthia Phelps, Principal Viola Carter Brey, Principal Cello The New York Philharmonic...
Scott Kirby- 35 Years of Songs & Stories w/ Mike Michaels at Key West Theater
Singer, songwriter, guitarist, storyteller, traveler and road warrior are all words that aptly describe Scott Kirby. Finishing songs while driving...
Presidential Families Weekend Forum
Join history enthusiasts and presidential descendants for Presidential Families Weekend from February 15-17, 2025, at Florida's only presidential site...