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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.
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.
FWC Florida Keys Regional Wave Regatta
Upper Keys Sailing Club · Details at regattanetwork.com ↗
Three-day Hobie Wave regional regatta on Buttonwood Sound, hosted by the club in Key Largo.
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.
Upper Keys Sailing Club · Details at upperkeyssailingclub.com ↗
Week-long A-Class catamaran midwinter regatta off Key Largo, open to fleet sailors from outside the club.
Upper Keys Sailing Club, Mark Sorensen Youth Sailing Program · Details at regattanetwork.com ↗
The Mark Sorensen Youth Sailing Program's regatta, sailed from Rowell's Waterfront Park on Blackwater Sound. Optis, youth ILCAs, Club 420s and windsurfers, ages 8 to 18; 18th running.
Force 5 Midwinter Championship
Upper Keys Sailing Club · Details at force5class.org ↗
Force 5 class midwinter championship off Key Largo, hosted by the club's resident Fleet 50.
Upper Keys Sailing Club · Details at snipeusa.com ↗
SCIRA midwinter regatta for the Snipe class on Buttonwood Sound, the circuit's Florida stop.
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 →
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 Largo
Nonprofit youth sailing program on Buttonwood Sound, sailing from the Upper Keys Sailing Club beach in Key Largo. Summer, fall, spring and homeschool sessions for ages 6 to 18 in Optis, Club 420s and RS dinghies, scholarships, and host of the Buccaneer Blast each February.
The Keys · Marathon
Youth sailing nonprofit at the Marathon Yacht Club, teaching ages 7 to 17 in Blue Dragons, Optis, Lasers, Sunfish and Flying Scots. The Sailing into STEM curriculum pairs boat handling with marine science, and scholarships keep it open to every Middle Keys family.
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.
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. Summer youth sailing for ages 7 to 17, run by the MYC Educational Foundation.
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. Rent a boat you sail yourself in Key Largo, Key West, and Marathon. All Florida sailboat rentals → See all Florida charter companies →
Featured Daysail The Keys · Marathon
Sirius is a Coast Guard inspected 36-foot sailing catamaran carrying 24 guests from Safe Harbor Marathon Marina, running two-hour sunset cruises by the seat and private charters. Capt. Dale Kamerzel has run the company since 2000. Siriusly Nauti is a motor boat.
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.
The Keys · Key Largo
Leopard catamaran fleet working the Keys out of Marina Del Mar in Key Largo since 1988, with further docks in Key West and on Stock Island. Bareboat or captained, by the day, the sunset or overnight, to the Keys and the Bahamas. Bareboat asks for time on a comparable catamaran.
The Keys · Marathon
Bareboat and captained charters from Keys Fisheries Marina, gulfside Marathon at mile marker 49. 27- to 36-foot Catalina and Irwin cruisers and a Beneteau 51, by the day or in three-day, two-night packages within 50 miles, Key West included; a checkout stands in for paperwork.
The Keys · Key Largo
Cottage-and-sailboat package on the bayside of Key Largo. Rent a cottage and, if you are a qualified sailor with recent time on the water, the 22-foot Catalina at the dock is yours to sail inside Florida Bay at no charge. Larger boats and captained trips cost extra.
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 · Marathon
Chao Lay is a 2006 Bavaria 50 that has sailed around the world, now running day and sunset sails from Yacht Haven Marina in Marathon. Six guests at a time through Boot Key Harbor, Hawk Channel and the Florida Keys Marine Sanctuary. Capt. Mike goes out in calm weather only.
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.
The Keys · Key Largo
Baker's Cay, the resort on the bayside of Key Largo, keeps 14-foot Hobie Waves on its beach through Scuppers, by the hour, briefing and life vest included, open to beginners and old hands alike. The same company runs a second base on St. Pete Beach.
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.
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Keep exploring: Sailing guides Florida events calendar ASA schools Bareboat charters