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
Flamy Grant in Concert
Jan 6 - 7, 2026
The Studios of Key West presents Flamy Grant, the award-winning drag artist and singer-songwriter whose powerhouse vocals, sharp wit, and soulful...
Key West
Rams Head Presents: Los Lobos
Jan 6, 2026
Experience an unforgettable night in the Florida Keys as Rams Head Presents Los Lobos! Enjoy the legendary band’s unique blend of rock, blues, and...
Key West
THE QUEENS OF COUNTRY: PATSY! DOLLY! LORETTA!
Jan 7 - 10, 2026
Christine Mild will return to the Barn with her latest musical special event, “The Queens of Country: Patsy! Dolly! Loretta!”. The show will have only...
Key West
Musical Benefit for Jamaica at William Weech American Legion Post 168
Jan 7, 2026
Escape to Key West for Musical Benefit for Jamaica on Jan 7, 2026 at William Weech American Legion Post 168. Doors 3 PM, show 4 PM. Live ensemble led...
Featured
Key West
Ben Harrison at Key West Theater
Jan 8, 2026, Jan 21, 2026, Feb 5, 2026, Mar 5, 2026, Mar 25, 2026
Show Dates: Jan 8, 21 Feb 5, 17 March 5, 25 IRREVERENT, FUNNY, and FULL OF KEY WEST, Ben is the author of the musicals UNDYING LOVE, EL ISLEÑO: The...
Key West
Edel Rodriguez: WORM: A Cuban American Odyssey
Jan 8 - 29, 2026
WORM: A Cuban American Odyssey The Studios of Key West presents WORM: A Cuban American Odyssey, an exhibition by internationally acclaimed artist and...
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Marathon
THE ODD COUPLE at Marathon Community Theater
Jan 8, 2026, Jan 9, 2026, Jan 10, 2026, Jan 15, 2026, Jan 16, 2026, Jan 17, 2026, Jan 22, 2026, Jan 23, 2026, Jan 24, 2026, Jan 25, 2026, Jan 29, 2026, Jan 30, 2026, Jan 31, 2026
JANUARY 8, 9, 10 @ 8:00PM JANUARY 15, 16, 17 @ 8:00 PM JANUARY 18 @ 3:00 PM-SUNDAY MATINEE JANUARY 22, 23, 24 @ 8:00PM JANUARY 25 @ 3:00PM -SUNDAY...
Marathon
Women of Wing Clinic
Jan 8 - 11, 2026
Escape to the Florida Keys for a transformative Women of Wing retreat! Enjoy sun-soaked days, wellness workshops, inspiring connections, and...
Key West
RAMS HEAD PRESENTS: ROBYN SCHALL'S HOLIDAY EXTRAVAGANZA TOUR
Jan 9, 2026
Experience holiday magic in the Florida Keys! Don’t miss Robyn Schall’s Holiday Extravaganza at the Key West Theater on Janurary 9. Enjoy an evening...
Islamorada
Fish for Holly Sailfish Tournament (2026)
Jan 9 - 11, 2026
Every donation you make, every act of generosity, becomes a part of Holly's legacy. By supporting The Holly Given Fund, you're not just contributing...
Key West
Analogous: Old Cameras. New Work. An Experiment in Analog Photography by Key West Artists Michael Marrero and Mark Hedden
Jan 9, 2026
Exhibit Runs January 9, 2026 - February 15, 2026 Analogous Old Cameras. New Work. An Experiment in Analog Photography by Key West Artists Michael...
Marathon
Florida Keys Celtic Festival
Jan 10 - 11, 2026
Experience the vibrant Florida Keys Celtic Festival! Enjoy lively Celtic music, thrilling Highland games, authentic food, and family-friendly fun in a...
Key West
Save Our First Responders 5K Sponsored By Shatterproof FHE Health
Jan 10, 2026
Join us in Key West for the Save Our First Responders 5K! Enjoy a scenic run or walk through paradise while supporting our local heroes. Perfect for...
