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. 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 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.
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. 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.
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.
The closest other metros we cover.
Looking wider than Key West? See everything in The Florida Keys, or browse all Florida sailing schools, yacht clubs, and charter companies.
