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.
The proposition is unusual enough to spell out: you rent a cottage on the bayside of Key Largo, and the sailboats come with it. Not as a paid extra: private sailboat use is included in the stay, along with kayaks, canoes, paddleboards, snorkeling gear, fishing tackle, and bicycles, under a stated no-hidden-charges policy. For a sailing family, that changes the arithmetic of a Keys week entirely: the boat is at the dock behind the cottage, and Florida Bay starts at the seawall.
The water is the other half of the argument. The bayside of the Upper Keys is shallow, protected, and scattered with mangrove islands, forgiving water for rusty skippers and honest water for learning, which is why American Sailing Academy teaches the ASA courses on site. Come as a beginner, leave with the certification and a week of unsupervised practice behind it; there are worse curricula.
The repeat-guest culture tells you what the place is. Reviews run to people on their tenth consecutive year, and the operation carries a TripAdvisor Travelers’ Choice award. It is cottages, boats, and the bay, run for people who think that is the whole point.
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.