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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Islamorada
34th Annual Florida Keys Island Fest
Mar 28 - 29, 2026
Each spring, the Florida Keys Island Fest brings two days of vibrant community celebration to Founders Park in Islamorada. Organized by the Islamorada...
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Key West
A ROCK SAILS BY at Red Barn Theater
Mar 31, 2026, Apr 4, 2026, Apr 7, 2026, Apr 11, 2026, Apr 14, 2026, Apr 18, 2026, Apr 21, 2026, Apr 25, 2026
Mar 31 - Apr 25, 2026 Shows: Tuesdays-Saturdays at 7:30pm When a UFO is sighted heading towards Earth, astrophysicist Dr. Lynn Cummings grants an...
Key West
RAMS HEAD PRESENTS: SQUIRREL NUT ZIPPERS
Apr 2, 2026
The Squirrel Nut Zippers celebrate the 30th anniversary of their platinum-selling album Hot! For this special show, the Zippers will perform Hot in...
Key West
Spanish Fly Shark Tournament (2026)
Apr 2 - 4, 2026
Experience the thrill of the Key West Shark Tournament in the beautiful Florida Keys! Join fellow anglers for exciting shark fishing, cash prizes, and...
Islamorada
28th Afro Roots Fest
Apr 3 - 5, 2026
Experience the vibrant Afro Roots Fest in the Florida Keys! Afro Roots Fest has historically celebrated the widespread influence that Africa continues...
Key West
Keith Sykes at Key West Theater
Apr 3, 2026
Experience an unforgettable island evening with legendary troubadour Keith Sykes at Key West Theater on April 3, 2026. Enjoy storytelling, timeless...
Key West
First Look Staged Reading series at The Studios - My Maria by Andrew Russell Directed by Morgan Green
Apr 3 - 4, 2026
MY MARIA - Andrew Russell's daring, genre-shifting play arrives in Key West: a romantic-comedy turned surreal thriller and then a raw, human drama...
Key West
Anne McKee Artists Fund Performance featuring Belle Jampol at Tennessee Williams Theater
Apr 4, 2026
Join us in Key West for an intimate, uplifting night with rising star Belle Jampol — a soulful mix of jazz, folk and roots. Experience heartfelt...
Key West
9th Annual Easter Egg Roll
Apr 4, 2026
Join the 9th Annual Easter Egg Roll at the Truman Little White House in Key West on April 4, 2026 (9–11AM). RSVP for the 9:30 or 10:30 egg hunts...
Key West
Puppy Pals, Live! at Tennessee Williams Theater
Apr 6, 2026
Part of the new Family Fun Series, which is designed to bring engaging and exciting performances for audiences of all ages to the Key West community...
Key West
RAMS HEAD PRESENTS: Crystal Gayle
Apr 7, 2026
Crystal Gayle brings her legendary voice and timeless songs to the Key West Theater for an unforgettable live performance. A Grammy Award–winning...
Key West
Mike Wiley at the American Legion Post 168
Apr 8 - 9, 2026
Mike Wiley brings Tired Souls and Breach of Peace to Key West—powerful solo plays about the Montgomery Bus Boycott and the Freedom Rides. April 8–9 at...
Featured
Key West
Waterfront Playhouse - Accomplice (Mainstage Series)
Apr 9, 2026, Apr 10, 2026, Apr 11, 2026, Apr 12, 2026, Apr 13, 2026, Apr 14, 2026, Apr 15, 2026, Apr 16, 2026, Apr 17, 2026, Apr 18, 2026, Apr 19, 2026
Apr 9, 2026 - Apr 18, 2026 A deliciously twisted comic thriller by Tony Award winner Rupert Holmes. Winner of the Edgar Award for Best Mystery Play...
Key West
Key West International Dance Company - "DARK NIGHT OF THE SOUL"
Apr 9 - 11, 2026
April 9, 10, 11, 15, 16, 17, 18, 22, 23, 24, 25 This is a rock ballet set to extraordinary music by Dan Krysa, set in 16th Century Spain. It tells the...
Key Largo
Key Largo Anglers Club Annual Offshore Tournament & Interclub Sailfish Challenge
Apr 11 - 12, 2026
Experience world-class fishing in the Florida Keys! Enjoy stunning ocean views, vibrant local culture, and the thrill of the catch. Plan your...
Marathon
7 Mile Bridge Run
Apr 11, 2026
Experience the iconic 7 Mile Bridge Run in the Florida Keys — 45th Annual on April 11, 2026 at 6:45 AM. Scenic 7‑mile course across the Overseas...
