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
Islamorada
Islamorada Junior Sailfish Tournament
Dec 12 - 14, 2025
Set sail for adventure in the Florida Keys with Isla Junior Sailing! Enjoy hands-on sailing experiences, stunning ocean views, and fun for all ages...
Islamorada
Fish for Holly Sailfish Tournament (2026)
Jan 9 - 11, 2026
Every donation you make, every act of generosity, becomes a part of Holly's legacy. By supporting The Holly Given Fund, you're not just contributing...
Islamorada
Islamorada Fishing Club Captain's Cup Sailfish Tournament
Jan 20 - 21, 2026
Presented by the Islamorada Fishing Club, the Captain’s Cup Sailfish Tournament is the second in the three-tournament Sailfish Championship series...
Islamorada
Cheeca Lodge & Spa Presidential Sailfish Tournament
Jan 23 - 25, 2026
The Cheeca Lodge Presidential Sailfish Tournament takes place January 23rd through 25th in Islamorada and serves as the final leg of the three...
The Lower Keys
22nd Annual Nautical Expo
Jan 24 - 25, 2026
The Lower Keys Chamber of Commerce welcomes you to one of our biggest events with over 100 vendors who showcase a variety of nautical items. Boating...
Key West
King Master
Jan 28 - 31, 2026
Experience the thrill of the ultimate King Master fishing event in the stunning Florida Keys, where turquoise waters meet endless adventure. Set...
Islamorada
Swamp Guides Ball
Jan 30 - 31, 2026
The Swamp Guides Ball returns bringing together anglers of all experience levels for a fun-filled, all-release backcountry fishing tournament...
Islamorada
Islamorada Women's Sailfish Tournament IWST (2026)
Jan 30 - Feb 1, 2026
Experience the ultimate getaway in the Florida Keys with Ladies, Let's Go Fishing! Join us for a fun, hands-on weekend of fishing, learning, and...
The Lower Keys
Annual Spanish Fly Music Festival
Feb 1, 2026
The 8th Annual Spanish Fly Music Festival is set for Sunday, February 1, 2026 at Boondocks Grille & Draft House on Ramrod Key! What started as a way...
The Lower Keys
Cuda Bowl Fishing Tournament (2026)
Feb 5 - 7, 2026
Join us in the Florida Keys for the legendary Cuda Bowl! Experience world-class flats fishing as anglers compete to catch barracuda in a fun...
