Directory
Sail without owning the boat. Bareboat charters for skippers with ASA-103/104 in pocket, crewed yachts when you want the captain included, monthly membership clubs, and seat-of-the-pants daysails. Rent a sailboat by the day or by the week. Filter by region or type, or submit a company we missed.
Or browse a region hub: Tampa Bay & Gulf Coast The Keys Miami & Southeast Northeast Panhandle Inland Lakes & ICW
Featured Daysail Northeast · St. Augustine
76-foot replica blockade-runner schooner sailing out of the City Marina in St. Augustine. Day sails, sunset sails, and moonlight sails. The city's longest-running tall-ship daysail.
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.
Featured Tampa Bay · Cape Coral
Charlotte Harbor and Pine Island Sound bareboat operator working out of Tarpon Point Marina in Cape Coral. Sister to Florida Sailing & Cruising School. The same fleet runs ASA instruction one week and bareboat charter the next.
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.
Crewed Miami / Southeast · Fort Lauderdale
Crewed-yacht broker and charter company whose US base sits on Fort Lauderdale's "Yachting Capital" mile. Books captained sailing yachts from a fleet that ranges through the Caribbean, the Bahamas, and Florida's east coast.
Crewed Panhandle · Fort Walton Beach
Private crewed catamaran daysails on a Stiletto 27 from Adventure Marina on Okaloosa Island. Crab Island, Santa Rosa Sound, sunset and snorkel runs for up to six guests, skippered by a national-champion racing crew of two.
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.
Panhandle · Pensacola Beach
Long-running Pensacola Beach watersports operation on Santa Rosa Sound. Small-boat sailboat and catamaran rentals, sunset sails, and lessons bundled with every rental. A beachfront fixture on the Pensacola side of the Panhandle.
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.
Crewed Tampa Bay · Clearwater
Charter arm of the MarineMax dealership network, headquartered in Clearwater. Books crewed luxury sailing and motor yachts for the British Virgin Islands, the Bahamas, and Florida. Closer to a brokered charter than a local fleet.
Daysail Northeast · Fernandina Beach
Daysail and private charter on Amelia Island, the northernmost barrier island in Florida. Two-hour to half-day sails on a 40-foot J/40 sloop out of the Fernandina Harbor Marina, with the Cumberland Sound and the marsh side both reachable in a session.
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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