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
Jimmy Buffett’s Coral Reefer Band
Jan 16, 2026
Jimmy Buffett’s Coral Reefer Band – Keepin’ the Party Going For over five decades, Jimmy Buffett and The Coral Reefer Band created the soundtrack to...
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
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
Bougie Afternoon Tea Party
Jan 17, 2026
Indulge in elegance at the Bougie Afternoon Tea Party in Key West! Savor gourmet teas, decadent treats, and live entertainment in a chic setting...
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...
Key West
The Southernmost Regatta
Jan 19 - 24, 2026
Experience the thrill of The Southernmost Regatta in the stunning Florida Keys! Enjoy world-class sailing, vibrant parties, and breathtaking ocean...
Key West
Kelly McGillis Classic
Jan 20 - 26, 2026
Join the 2026 Kelly McGillis Classic in the beautiful Florida Keys! Enjoy exciting women’s and girls’ flag football tournaments, beachside fun, and...
Islamorada
Islamorada Fishing Club Captain's Cup Sailfish Tournament
Jan 20 - 21, 2026
Presented by the Islamorada Fishing Club, the Captain’s Cup Sailfish Tournament is the second in the three-tournament Sailfish Championship series...
Featured
Key West
AT THE WEDDING at Red Barn Theater
Jan 20, 2026, Jan 24, 2026, Jan 27, 2026, Jan 31, 2026, Feb 3, 2026, Feb 7, 2026, Feb 10, 2026, Feb 14, 2026
Jan 20 - Feb 14, 2026 Shows: Tuesdays-Saturdays at 7:30pm Patrons will be cordially invited to a Northern California wedding and meet Carlo, an agent...
Key West
Key West International Dance Company - "LAMBADA IS DEAD: LONG LIVE LAMBADA!"
Jan 20 - 24, 2026
This popular show - that wowed audiences in our inaugural season - returns in 2026. With stunning dance numbers, thrilling music by Gil Semedo and...
Featured
Key West
70 Girls 70 at Fringe Theater
Jan 21, 2026, Jan 22, 2026, Jan 23, 2026, Jan 24, 2026, Jan 25, 2026, Jan 26, 2026, Jan 27, 2026, Jan 28, 2026, Jan 29, 2026, Jan 30, 2026, Jan 31, 2026
Jan 21 - Jan 31 Don’t miss the concert-style revival of 70 Girls 70, the delightfully irreverent Kander & Ebb musical running January 21–31. This...
Key West
The Music of ABBA at Tennessee Williams Theater
Jan 21, 2026
A fun colorful family show, all the way from Sweden! With hits like Mamma Mia, Waterloo, Fernando and Dancing Queen, ABBA, Sweden’s biggest music...
Key West
Rams Head Presents: Rumours ATL: A Fleetwood Mac Tribute
Jan 21, 2026
Experience the magic of Fleetwood Mac with Rumours ATL, the ultimate tribute band, live at Rams Head in Key West! Enjoy iconic hits, vibrant energy...
Key West
Honoring America’s First Ladies: Two-Night Series at the Harry S. Truman Little White House
Jan 23 - 24, 2026
The Harry S. Truman Little White House will host a two-night series on January 23–24, 2026, honoring the legacy and influence of America’s First...
