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
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 2 - 12, 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...
Key West
Rams Head Presents: The Brit Pack: The Ultimate British Music Experience
Jan 17, 2026
Experience the ultimate British music journey in the Florida Keys! Rams Head presents The Brit Pack, delivering iconic hits from legendary UK artists...
Key West
28th Annual Key West Half Marathon & Runfest
Jan 17 - 18, 2026
Experience the excitement of the Key West Half Marathon! Run through stunning oceanfront views, lively streets, and historic landmarks in the heart of...
Islamorada
Art Under the Oaks
Jan 17, 2026
Art Under the Oaks is a beloved annual tradition held beneath the beautiful oak trees on the grounds of San Pedro Church in Islamorada. This vibrant...
Key West
Yevgeny Kutik at Tennessee Williams Theater
Jan 18, 2026
With a “dark-hued tone and razor-sharp technique” (The New York Times), violinist Yevgeny Kutik has captivated audiences worldwide with an old-world...
