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
Race World Offshore (2025)
Nov 2 - 9, 2025
Step into the exhilarating world of Race World Offshore, where the ocean becomes a high-speed battleground for cutting-edge boats and fearless...
Featured
Key West
Key West Film Festival
Nov 12 - 16, 2025
Key West Film Festival transforms the island into a vibrant destination for film lovers, filmmakers, and critics from around the world. Set against...
Key West
Page Turner Adventures: The Magnificent Circus Mystery
Oct 28, 2025
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
Key West Bear Weekend 2025
Oct 29 - Nov 2, 2025
Key West Bear Weekend is back for 2025! After an amazing 2024, come back to the friendliest bear event ever in the beautiful paradise island of Key...
Islamorada
Pumpkin Carving Party
Oct 29, 2025
Get into the spooky spirit at the Pumpkin Carving Party at the Brewery, a festive fall celebration filled with creativity, craft beer, and community...
Key Largo
Trick-or-Treat at Divers Direct
Oct 30, 2025
Bring the kids for a spooktacular evening of trick-or-treating at Divers Direct Key Largo, located at 99621 Overseas Highway. On Thursday, October...
Key West
Trick Or Treat Halloween Party at Truman Waterfront
Oct 30, 2025
Join the FREE Family-Friendly Halloween Party at the Truman Waterfront Farmers Market on Thursday, October 31, from 4 p.m. to 7 p.m. (Market opens at...
Key Largo
Down the Rabbit Hole - Halloween in Wonderland
Oct 31, 2025
Join us for a Halloween adventure like no other as we step through the looking glass into a world of mad tea parties, curiosities, and magical...
Key West
Gathering of the Order of the Sleepless Knights
Oct 31 - Nov 1, 2025
The Order of the Sleepless Knights invites fans to experience a one-of-a-kind journey through Old Town Key West aboard a private charter with the...
Key West
Will Kimbrough
Oct 31, 2025
For Twenty years Will Kimbrough has been writing songs with Jimmy Buffett including 5 songs on the last album and one of those was “Bubbles Up”. And...
Key West
Human Interest: Portraits by Jack Baron - Exhibit Opening
Oct 31, 2025
Exhibit Runs October 31, 2025 - January 4, 2026 Human Interest: Portraits by Jack Baron This exhibition of luminescent needlepoint tapestries and...
Key West
Buffett Through The Years -Tribute Show
Oct 31, 2025
Get ready to be transported to the sunny shores of Key West as BeachFront Radio proudly presents “Buffett Through the Years" Tribute Show- an...
Marathon
The Sinister Speakeasy Halloween Party
Oct 31, 2025
The Palm Deck returns for another incredible season, kicking things off with The Sinister Speakeasy, a Halloween bash like no other. On Halloween...
Islamorada
I.CARE Underwater Critter Costume Party
Nov 1, 2025
Dive into the I.CARE Underwater Critter Costume Party in Islamorada! Join fellow ocean lovers for a unique snorkeling adventure where you and your...
Key West
Follow The Rabbit...
Nov 1, 2025
Step into The Rabbit’s Wonderland Speakeasy, an intimate, immersive show experience blending burlesque, dance, circus arts, and dazzling light shows...
Key West
ABC 5K & 10K
Nov 1, 2025
Join the Zonta ABC 5K Run/Walk in Key West! Enjoy scenic ocean views, a vibrant community atmosphere, and support breast cancer awareness. Perfect for...
Key West
Rams Head Presents: Dead-Zep
Nov 1, 2025
Experience an unforgettable night in the Florida Keys as Rams Head Presents: Dead Zep! Enjoy the electrifying sounds of Grateful Dead and Led Zeppelin...
