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A 113-mile archipelago of turquoise water, reef anchorages, and Key West sundowners. Trade-wind cruising at its easiest, and the jumping-off point for the Bahamas and Dry Tortugas.
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Sailing by city: Key West Marathon & the Middle Keys Key Largo & the Upper Keys
Regattas, race series, and championships hosted by clubs and schools across The Keys.
Sunfish Florida Regional Championship II
USSCA Florida-region Sunfish championship on Buttonwood Sound, a Sunfish World Championship qualifier.
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 →
ASA and US Sailing certifications, plus introductory programs. See all Florida schools →
The Keys · Key Largo
ASA school on Buttonwood Sound, teaching from the Key Lime Sailing Club cottages at mile marker 99. Courses run on demand 363 days a year; stay in a cottage, learn on Florida Bay, and keep sailing the club's Catalina 22s free after you certify.
The Keys · Marathon
Middle-Keys ASA school running the full coastal-cruising pathway from Basic Keelboat through Advanced Coastal Cruising out of Marathon.
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 toward the Dry Tortugas, the Marquesas, or the Bahamas.
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 train at no charge one weekend a month through the winter season.
The Keys · Tavernier
Upper Keys ASA school running liveaboard course-vacations from Tavernier, with certifications earned on multi-day cruises through the Keys and out to the Bahamas. The owner-instructor is a six-time ASA Outstanding Instructor of the Year.
The Keys · Tavernier
Upper Keys ASA school founded by a Navy SEAL, with a "crawl, walk, run" curriculum built around veterans, their supporters, and couples. Active-duty and honorably discharged military earn their ASA certifications free of charge.
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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.
Private The Keys · Marathon · est. 1951
Middle Keys private club founded 1951 on the Gulf side of Marathon. FCYC member with full reciprocity across Florida's private yacht clubs. Slips, dining, and pump-out for visiting reciprocal members.
Community The Keys · Key Largo · est. 1973
Nonprofit community club on Buttonwood Sound in Key Largo, founded 1973. Year-round race calendar, youth programs, and a regular regatta venue for Florida District 7 Flying Scot events.
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Bareboat, crewed, daysail, and membership charters: sail without owning. 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 out of the Historic Seaport. Sunset cruises, Sunday brunch sails, day trips, and private events, with food and drink included in every ticketed trip.
The Keys · Key Largo
Cottage-and-sailboat package on the bayside of Key Largo. Stay in one of the rental cottages, sail one of the included Catalina sloops day-by-day inside Florida Bay. No bareboat resume required for the sub-25-foot fleet.
Daysail The Keys · Key West
Three wooden schooners sailing from the Historic Seaport. Champagne sunset sails and windjammer day sails on the 86-foot Appledore II (Key West winters), backcountry eco tours on the bugeye Appledore Star, 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.
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