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...
Featured
Islamorada
Morada Way Third Thursday Art Walk
Nov 20, 2025, Dec 18, 2025, Jan 15, 2026, Feb 20, 2026, Mar 19, 2026, Apr 16, 2026, May 21, 2026, Jun 18, 2026, Jul 16, 2026, Aug 21, 2026, Sep 17, 2026, Oct 15, 2026
Dates: Third Thursday of each month from 6 to 9pm Experience the vibrant Morada Way Arts & Cultural District Art Walk in the Florida Keys! Enjoy local...
Featured
Key West
Waterfront Playhouse -Some Enchanted Evening (Mainstage Series)
Dec 4 - 20, 2025, Dec 5 - 21, 2025, Dec 6 - 22, 2025, Dec 7 - 23, 2025, Dec 8 - 24, 2025, Dec 9 - 25, 2025, Dec 10 - 26, 2025, Dec 11 - 27, 2025, Dec 12 - 28, 2025, Dec 13 - 29, 2025, Dec 14 - 30, 2025, Dec 15 - 31, 2025, Dec 16, 2025 - Jan 1, 2026, Dec 17, 2025 - Jan 2, 2026, Dec 18, 2025 - Jan 3, 2026, Dec 19, 2025 - Jan 4, 2026, Dec 20, 2025 - Jan 5, 2026
Dec 4, 2025 - Dec 20, 2025 A stunning revue of Rodgers & Hammerstein’s most treasured songs, this elegant theatrical presentation brings five...
Featured
Key West
Personal Effects at Fringe Theater
Dec 9, 2025, Dec 10, 2025, Dec 11, 2025, Dec 12, 2025, Dec 13, 2025
Dec 9 - Dec 13 Experience the world premiere of Personal Effects by local playwright Chris Moore, running December 9–13. When the adult children of a...
Key West
Femmes of Rock at Key West Theater
Dec 10, 2025
Experience an unforgettable night in the Florida Keys at Key West Theater! Don’t miss “Rumours of Fleetwood Mac” on Nov 16, 2025—a world-class tribute...
Key West
Rams Head Presents: Anthony Rodia: Laugh Til It Hurts Tour
Dec 11, 2025
Experience a night of laughter in Key West as Rams Head presents Anthony Rodia’s “Laugh ‘Til It Hurts” Tour! Don’t miss this hilarious stand-up comedy...
Key West
Key West International Dance Company - "Country Christmas"
Dec 11 - 12, 2025
Experience the vibrant rhythms of Key West International Dance Company in the Florida Keys! Enjoy captivating performances, diverse dance styles, and...
Key West
Scott Kirby - 35 Years of Songs & Stories at Key West Theater
Dec 11, 2025
Singer, songwriter, guitarist, storyteller, traveler and road warrior are all words that aptly describe Scott Kirby. Finishing songs while driving...
Key West
Conch Tour Train's Holiday Sights & Festive Nights Tours
Dec 11 - 23, 2025
Climb aboard the lively Conch Tour Train for a festive holiday ride through Key West’s most brilliantly decorated neighborhoods, homes, and historic...
Key West
Robert Albury “Key West’s King of Soul” at Williams Hall
Dec 11, 2025
Experience the soulful sounds of Robert Albury, the "Mayor of Bahama Village," live at Williams Hall in Key West! Enjoy an unforgettable evening of...
Islamorada
Islamorada Half Marathon, 10K, Rumrunner Run & Beach N' Beer Mile
Dec 11 - 14, 2025
Experience the ultimate island adventure at the Islamorada Running Company’s events in the Florida Keys! Enjoy scenic races, tropical vibes, and post...
Marathon
Hawk’s Cay Marina Grand Re-Opening
Dec 12 - 14, 2025
Following a complete redesign and enhancement, Hawks Cay Marina welcomes you back with a celebration-filled weekend. On Friday night, get in the...
Key West
December Duo Holiday Concert: Irie Monte and Crispin Campbell at The Studios of Key West
Dec 12, 2025
Enjoy an enchanting evening of live string music under the stars as Irie Monte and Crispin Campbell perform together on the rooftop. Violinist Irie...
Key West
Holiday Fest-Inn Tours
Dec 12, 2025
Experience the magic of Key West at the Holiday Historic Inn Tour on December 12! Explore festively decorated historic inns, enjoy holiday treats, and...
Key West
The Art of Accuracy: Drawing Essentials with Samuel Alvarez at The Studios of Key West
Dec 12 - 13, 2025
Dec 12 - 13 Discover "The Art of Accuracy" with Samuel Alvarez at The Studios of Key West! Dive into a captivating exploration of precision in art...
Key West
Holiday Concert & Bazaar at Custom House
Dec 12, 2025
Experience the festive spirit at the Holiday Bazaar in the Florida Keys! Enjoy unique gifts from local artisans, live music, delicious treats, and a...
