Regattas, race series, and championships hosted by clubs and schools across Key West.
Key West Community Sailing Center · Details at kwcsc.org ↗
The center's seventh annual Halloween Regatta on Garrison Bight, racing with costumes and prizes, open to members and visiting sailors.
Key West Community Sailing Center · Details at kwcsc.org ↗
Second running of the center's youth regatta: Optimists in the Naval Basin off Truman Waterfront, ILCA 4/6 and 420s on the ocean course off Fort Zachary Taylor. Ages 8 to 19; entry open.
Key West Community Sailing Center · Details at kwcsc.org ↗
The center's annual distance race around Key West; the 52nd edition was sailed in April 2026.
Live wind and sky, spot by spot, straight from the National Weather Service. Each card opens the full point forecast. NWS Key West marine forecast →
Learn to sail, ASA and US Sailing certification courses, and private lessons. ASA courses in Key West are taught by Sail Away Key West and Southernmost Sailing School. All Florida ASA schools → See all Florida schools →
The Keys · Key West
Catamaran charter operation at Stock Island Marina Village with an ASA school built in, teaching Basic Keelboat through catamaran cruising on multi-day training cruises. Courses run as customized liveaboards around Key West, across to the Bahamas, or up on the Chesapeake.
The Keys · Key West
Key West ASA school sailing from Stock Island since 2014, in classes of two to four on the calm Gulf side of the island. Veterans are offered a discover-sailing cruise and a discount on the courses, one weekend a month through the winter season.
Member-driven yacht clubs and community sailing centers. See all Florida clubs →
Community The Keys · Key West
Nonprofit community sailing center at Garrison Bight in Key West: affordable learn-to-sail, youth summer programs, and member sailing on a fleet of small boats in the protected basin, going strong for half a century.
Private The Keys · Key West · est. 1938
Southernmost private yacht club in the United States, founded 1938 in a former bridge tender's house on Garrison Bight. 68 wet slips, full dining room, ramp, and ship's store.
Bareboat, crewed, daysail, and membership charters: sail without owning. Rent a boat you sail yourself in Key West from Sunset Watersports. All Florida sailboat rentals → See all Florida charter companies →
Featured Daysail The Keys · Key West
Crewed daysails on Hindu, a 1925 gaff-rigged schooner designed by William H. Hand Jr. as a half-scale Grand Banks fisherman, later a WWII Navy patrol boat and Provincetown whale-watcher. Winter sunset and daytime sails out of the Historic Seaport.
Daysail The Keys · Key West
Year-round crewed sails on a 75-foot Key West-built catamaran from Sunset Pier at the foot of Duval Street. Public sunset cruises and Sunday brunch sails, private daysails and events, with food and drink included in every fare.
Daysail The Keys · Key West
Three wooden schooners sailing from the Historic Seaport. The 86-foot windjammer Appledore II in Key West winters, champagne sunset sails and backcountry eco tours on the bugeye Appledore Star, sunset and dolphin sails and private charters on the 43-foot Valora.
Daysail The Keys · Key West
74-foot topsail schooner built 1982–83, long the unofficial flagship of the Conch Republic and, since 2023, flagship of Key West. Currently laid up at a Key West boatyard and not sailing. Her nonprofit is fundraising a full restoration.
Daysail The Keys · Key West
Long-running Key West daysail outfit operating large cruising catamarans out of the Historic Seaport. Sunset, reef-snorkel, and full-day sail-and-snorkel itineraries crewed by USCG-licensed captains. Sister operation Key West Schooners covers the wooden-schooner side.
The Keys · Key West
Hobie Wave and Hobie Getaway rentals from two huts on Smathers Beach, the sailing half of a Key West watersports operation running since 1984. Walk-up only, daily 9 to 5, with paddleboards and kayaks on the same beach.
The closest other metros we cover.
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