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
Fantasy Fest
-
Fantasy Fest is an electrifying, 10-day costume and performance festival held annually in Key West, Florida, each October. First launched in 1979 by...
Featured
Key West
Fly Into Fantasy Fest with Tropic Ocean Airways
October 15, 16, 18, 22, 23 and 25, 2026. Skip the Overseas Highway and take to the skies during Fantasy Fest with Tropic Ocean Airways’ nonstop...
Featured
Key West
Hedwig and the Angry Inch at Waterfront Playhouse
October 15-23, 2026 Hedwig and the Angry Inch opens Waterfront Playhouse’s 88th season with a bold and electrifying rock musical experience presented...
Featured
Islamorada
Morada Way Third Thursday Art Walk
-
Every third Thursday of the month from 6 to 9 p.m., Morada Way in Islamorada comes alive with color, music, flavor, and island charm. Stroll through...
Featured
Islamorada
Casting for Cats Backcountry Tournament
-
October 16–17, 2026 | Islamorada Cast a line for a great cause at the annual Casting for Cats Backcountry Fishing Tournament, a longtime Upper Keys...
Featured
Islamorada
Ladies, Let's Go Fishing! Keys Saltwater Weekend
-
October 16–18, 2026. Discover the excitement of sportfishing in a fun, supportive environment during the Ladies, Let’s Go Fishing! Keys University and...
Featured
Islamorada
The Hoy Shanty Crew Sing-Along
Saturday, October 17, 2026, from 6 to 8 p.m. Raise your voice and discover the musical traditions of life at sea during the first-ever Hoy Shanty Crew...
Featured
Islamorada
Cortadito: A Tribute to the Buena Vista Social Club
Monday, October 19, 2026, at 6 p.m. Experience the rhythms of traditional Cuban music when Cortadito brings its tribute to the legendary Buena Vista...
Featured
Key West
The Greatest Hits Pool Party
Tuesday, October 20, 2026, from noon to 4 p.m. Dress like an icon and sing like a legend during the Greatest Hits Pool Party at Winslow’s Bungalows...
Featured
Key West
Rum Revelations: A Cocktail Adventure
Available on select dates October 20–24 and October 27–31, 2026. Mix, shake, and sip your way through the world of rum during Rum Revelations: A...
Key Largo
REEF Ocean After Hours - Waterlust Trivia #1
Tuesday, October 20, 2026 at 6:00 PM. The Waterlust Trivia Challenge is back at the REEF Ocean Exploration Center in Key Largo, and REEF is not going...
Featured
Key West
Key West History Through Five Craft Cocktails
-
Available October 20–24 and October 27–31, 2026, from 5 to 7 p.m. Raise a glass to Key West’s colorful past during Key West History Through Craft...
Featured
Key West
LUV2GLOW: Liquid Frequency
-
Get ready to light up the night at LUV2GLOW: Liquid Frequency, a two-night electronic and dance music experience taking over Rick’s Key West on...
Featured
Islamorada
Treasure Treat Night
Available on select dates October 20–24 and October 27–31, 2026. Mix, shake, and sip your way through the world of rum during Rum Revelations: A...
Featured
Key West
Rams Head Presents: Garrison Keillor and Erica Rhodes – The Crazy Uncle and His Sensible Niece
Settle in for an evening of storytelling, laughter, and quick-witted comedy as Garrison Keillor and Erica Rhodes take the stage for The Crazy Uncle...
Key Largo
REEF Ocean After Hours - Spooky Fish Bingo & Costume Contest
Tuesday, October 27, 2026 at 6:00 PM. Halloween week gets a little fishy in Key Largo. REEF is hosting a special round of Spooky Fish Bingo at the...
