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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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...
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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
This Blows: A Musical Comedy Show That Doesn't Suck at Key West Theater
Nov 21, 2025, Nov 22, 2025, Nov 23, 2025
Experience the hilarious, heartfelt, and unmistakably Key West spirit in “Written for Locals, By Locals, Starring Locals!” — the island’s newest...
Featured
Key West
Key West International Dance Company Presents "Florida Man: The Musical"
Nov 21, 2025, Nov 22, 2025, Nov 23, 2025, Nov 28, 2025, Nov 29, 2025, Nov 30, 2025
Show Dates: November 21, 22, 23, 28, 29, 30 The show is a hilarious romp – as famous British naturalist David Attenborough roams the wilds of Florida...
Key West
Time to Talk Turkey! at Key West Cooking Show
Nov 22, 2025
Join the "Time to Talk Turkey" Key West Cooking Show in the Florida Keys! Enjoy a fun, interactive culinary experience where local chefs share tips...
Key Largo
Light Up Key Largo
Nov 22, 2025
Light Up Key Largo returns the Saturday before Thanksgiving, marking the official start of the holiday season in the Upper Keys. This annual...
Key West
Annual Rum Infused Garden Scavenger Hunt
Nov 22, 2025
Get ready for a night of adventure, flavor, and fun at the Third Annual Rum-Infused Adult Scavenger Hunt at the Key West Tropical Forest & Botanical...
Key West
Tour de Keys
Nov 22, 2025
On Saturday, November 22, 2025, join riders from across the country for a stunning charity ride from Key Largo or Marathon to iconic Key West. Choose...
Key West
3rd Annual Rum Infused Adult Scavenger Hunt
Nov 22, 2025
Join the 2025 Rum-Infused Adult Scavenger Hunt in Key West! Explore lush gardens, solve fun clues, and enjoy rum tastings at every stop. Perfect for...
Key West
Rams Head Presents: Crystal Gayle
Nov 22, 2025
CMA’s “Female Vocalist of the Year” for two consecutive years, Crystal is also a Grammy® Award winner for “Best Female Vocal Performance” thanks to...
Key West
1st Annual USCGC Ingham Fundraising Gala
Nov 22, 2025
Join us in the beautiful Florida Keys for the USCGC Ingham Maritime Museum’s special event! Enjoy live music, delicious food, drinks, and stunning...
Key West
Carl Fest Grand Finale at Key West Theater
Nov 23, 2025
Get ready to rock with Carl Fest Grand Finale — a celebration of music, community, and the unstoppable spirit of Caffeine Carl at the Key West Theater...
Key West
An Evening of Cinema and Celebration: A Fundraising Birthday Fête for Sir Billy Connolly at Tropic Theater
Nov 24, 2025
Join us in Key West for "An Evening of Cinema and Celebration"—a fundraising birthday fête for Sir Billy Connolly at Tropic Cinema! Enjoy film...
Key West
Stargazing 101 with Larry Halstead at The Studios of Key West
Nov 24 - 25, 2025
Discover the wonders of the night sky in the Florida Keys! Join Stargazing 101 with Larry Halstead at The Studios of Key West. Perfect for leisure...
Key West
The Carole King & James Taylor Story ft. Phoebe Katis & Dan Clews
Nov 25, 2025
Following a critically acclaimed sell out run at The Edinburgh Fringe Festival, The Carole King & James Taylor Story takes you on an incredible...
Key West
Tony Baltimore- Dinner & a Show ft. Tim Conroy & Randy Stindt at Key West Theater
Nov 26, 2025
Come hungry — and come ready for an experience like no other. This unforgettable evening blends live music, storytelling, and heartfelt flavors in a...
