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.
See Some Shenanigans
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
Benmont Tench at Key West Theater
Feb 13, 2026
Experience an unforgettable night in the Florida Keys! See Benmont Tench & Graham Nash live on tour at the Key West Theater. Enjoy legendary music in...
Key West
Pilobolus at Tennessee Williams Theater
Feb 13, 2026
Pilobolus’s Other Worlds Collection traverses the spaces we inhabit—from the realms within ourselves, society, and the universe—with wit, wisdom, and...
Key West
A Tribute to The Songs of Pat Dailey w. Ray Fogg and Reese Dailey at Key West Theater
Feb 14, 2026
Ray Fogg and Reese Dailey will be teaming up to pay tribute to the songs of the legendary Pat Dailey. During his long career, Pat Dailey created an...
Key West
20th Annual Florida Keys Seafood Festival
Feb 14 - 15, 2026
Experience the vibrant flavors of the Florida Keys at the Seafood Festival! Enjoy fresh local seafood, live music, family-friendly activities, and...
Key West
Horszowski Trio at Tennessee Williams Theater
Feb 15, 2026
Impromptu Classical Concerts Giving performances that are “lithe, persuasive” (The New York Times), “eloquent and enthralling” (The Boston Globe), and...
Key West
RAMS HEAD PRESENTS: GABRIEL RUTLEDGE: DON'T READ THE COMMENTS TOUR
Feb 15, 2026
A past winner of both the Seattle International Comedy Competition and The Laughing Skull Comedy Festival in Atlanta, Gabriel has made numerous...
Featured
Key West
Letters from Max at Fringe Theater
Feb 18, 2026, Feb 19, 2026, Feb 20, 2026
Running February 18–20, Letters from Max by Sarah Ruhl is a tender meditation on art, mentorship, and the beauty of human connection. Based on the...
Key West
RAMS HEAD PRESENTS: YACHTLEY CREW
Feb 18, 2026
Set sail for smooth sounds and good-time vibes with Yachtley Crew – The Titans of Soft Rock, the world’s premier Yacht Rock band! Dressed in their...
Key West
Key West International Dance Company - 'GATE 54B'
Feb 19 - 21, 2026
February 19th, 20th, 21st, 24th, 25th, 26th, 27th, 28th Experience the vibrant rhythms of Key West International Dance Company in the Florida Keys...
Key West
RAMS HEAD PRESENTS: MARTY STUART AND HIS FABULOUS SUPERLATIVES
Feb 19, 2026
Experience an unforgettable night in the Florida Keys! Catch Marty Stuart and His Fabulous Superlatives live at the Key West Theater. Enjoy world...
Key West
Darcy Cooke Songs & Stories of the Silver Screen
Feb 20, 2026
Glamour, gossip, movies and music. Become a Hollywood insider for the evening, enjoying the songs and backstories of the music that made the movies...
Key West
Key West Art & Craft Festival
Feb 21 - 22, 2026
Experience the vibrant art scene of the Florida Keys at the Key West Art Center! Discover stunning local artwork, meet talented artists, and enjoy a...
Key West
Rimsky-Korsakov, Mozart,Joachim & Simon at Tennessee Williams Theater
Feb 21, 2026
Masterworks III: Rimsky-Korsakov's Capriccio Espagnol with Mozart, Joachim & Simon Featuring Seth Parker Woods, cello Simon Four Black American Dances...
Key West
Lower Keys Rotary Kids Fishing Tournament
Feb 22, 2026
Experience the best of the Florida Keys at the Lower Keys Rotary’s annual event! Don’t miss this chance to celebrate community and the Keys’ laid-back...
Key West
Garrison Keillor and Erica Rhodes: “The Crazy Uncle and His Sensible Niece" at Key West Theater
Feb 22, 2026
Experience an unforgettable evening in the Florida Keys with legendary storyteller Garrison Keillor at the Key West Theater! Enjoy humor, music, and...
