"Bareboat" means you charter the boat and skipper it yourself, no captain aboard. It's the most freedom, and the best value per person, for cruising the Keys, Biscayne Bay, or the Gulf coast. Here are the Florida companies that rent sailboats bareboat.
Before a company hands you the keys, expect them to want ASA 104 (Bareboat Cruising) or equivalent, plus a sailing resume, and sometimes a checkout sail for bigger boats or catamarans. New to it? See bareboat charter requirements, or book a crewed charter that comes with a captain. Planning the trip itself? Start with the Keys cruising itinerary.
In the islands themselves, the standing bareboat option is Key Lime Sailing Club on the bayside of Key Largo: rental cottages with Catalina sloops included, sailed day-by-day inside Florida Bay and the Upper Keys, and no bareboat resume required for the sub-25-foot fleet. For a bigger boat or a week-long cruise, Florida's larger bareboat fleets base outside the Keys (on the Gulf coast and around Biscayne Bay), so plan the delivery legs into your itinerary. The Keys cruising itinerary maps the anchorages and distances; the Florida Keys region hub has the local clubs, schools, and weather.
Want a captain, a day sail, or a membership instead? See all Florida sailboat charter companies, or browse by place: Key West, the Florida Keys, or the Gulf coast.
