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 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: 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...
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...
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...
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
RAMS HEAD PRESENTS: GIVEN TO FLY: A TRIBUTE TO PEARL JAM
Jan 10, 2026
Given to Fly recreates the power and passion of Pearl Jam's iconic sound and live show. Fronted by Bob Donahue, with his rich and resonant voice that...
Key West
RAMS HEAD PRESENTS: DAVID NIHILL: TAKING TANGENTS TOUR
Jan 11, 2026
Leaving Dublin, Ireland where he was born and raised until the age of 22, David got drunk on travel and never quite hit sobriety of it. He has lived...
Key West
Los Lobos at Key West Theater
Jan 13, 2026
It’s a matter of time. 50 years to be exact. And in that time Los Lobos have created an unprecedented body of work, a legacy of greatness.
Key West
5th Annual Key West Chick Fest
Jan 14 - 18, 2026
Join the ultimate girls’ getaway at Key West Chick Fest, April 14-18, 2026! Enjoy live music, beach parties, island adventures, and exclusive events...
Featured
Key West
Waterfront Playhouse Presents: Tuesdays With Morrie (Spotlight Series)
Jan 15, 2026, Jan 16, 2026, Jan 17, 2026
Jan 15, 2026 - Jan 17, 2026 A moving adaptation of Mitch Albom’s bestselling memoir, this play follows the touching reunion between a busy journalist...
Key West
Key West International Dance Company - "LAMBADA IS DEAD: LONG LIVE LAMBADA!"
Jan 15 - 17, 2026
January 15, 16, 17, 20, 21, 22, 23, 24 This popular show - that wowed audiences in our inaugural season - returns in 2026. With stunning dance numbers...
Key West
RAMS HEAD PRESENTS: ASLEEP AT THE WHEEL
Jan 15, 2026
Experience legendary Western swing with Asleep at the Wheel live at Key West Theater! Don’t miss this unforgettable night of music and fun in the...
Key West
Scott Kirby- 35 Years of Songs & Stories w/ Caffeine Carl at Key West Theater
Jan 15, 2026
Singer, songwriter, guitarist, storyteller, traveler and road warrior are all words that aptly describe Scott Kirby. Finishing songs while driving...
Key West
Kash'd Out at Key West Theater
Jan 16, 2026
Get ready for an electrifying night of reggae and rock as Kash’d Out brings their high-energy live show to the Florida Keys! Known for their clever...
Islamorada
Beats on the Bay - The 13th Annual Baygrass Bluegrass at Founders Park
Jan 16 - 19, 2026
Experience the Baygrass Bluegrass Festival in the Florida Keys! Enjoy live bluegrass music, local food, craft beer, and family-friendly fun in a...
Key West
Martina Bevis & Friends at Tennessee Williams Theater
Jan 16, 2026
Prague Conservatory of Music trained guitarist, Martina Bevis, returns to the Tennessee Williams Theatre. Join her along with her special guests to...
