Events in the Florida Keys
View our Events Calendar for activities and events going on each month in Key West and the Florida Keys
Events in Florida Keys for 2025
- Dec 15, 2025 - Mar 15, 2026
- Impromptu Classical Concerts - Key West 2026
- Website Tennessee Williams Theater
- 5901 College Rd Key West FL 33041
- 305-296-7676 E-mail
- Bringing world-class chamber music to Key West since 1972! From Jan–Mar 2026, enjoy six concerts with acclaimed ensembles and rising virtuosos, including Ulysses Quartet on Jan 4 and Yevgeny Kutik on Jan 16. More announcements coming soon.
- Dec 31, 2025 - Dec 31, 2025
- Boys & Girls Club New Year’s Eve Masquerade Fundraiser!
- Website Beachside Marriott Ballroom
- 3841 N Roosevelt Blvd Key West FL 33040
- Facebook Instagram
- Join us for “A Night in Disguise,” a black-tie affair benefiting the Boys & Girls Clubs of the Keys Area. Enjoy live & silent auctions, a comedian and drag show—raising funds for a new transportation bus! Get your tickets now or call to reserve tables!
- January 19 - January 24 Key West
- The Southernmost Regatta
- Website
- Top sailing teams from around the world compete in the azure waters off Key West, showcasing colorful sails and avid sportsmanship during five consecutive days of racing. Competition is open to One Design and ORC Racing / Cruising Keelboats. Spectators can watch the races from various waterfront venues, mingle with sailors and view sailboats at the Galleon Resort's marina, 617 Front Street, after each day’s races.
- January 30 - January 31 Islamorada
- 36th Annual Swamp Guides Ball Fishing Tournament & Auction1 a sea
- Website
- In this annual all-release competition, organized by the Florida Keys Fishing Guides Association, anglers target three species – bonefish, redfish and snook. The tournament benefits the Florida Keys Fishing Guides Foundation and the Guides Trust Foundation, organizations that provide funds to people in the local fishing industry in times of need. Guides are welcome to register and fish as anglers. Tournament activities take place at Safe Harbor Angler House, mile marker 80.5 bayside. The online auction is open to all, not just registered anglers.