Tampa Bay · Port Charlotte
Courageous, a 1983 Hunter 37 Cherubini, sails Charlotte Harbor from a Port Charlotte dock with Captain Curtis. Private day and sunset sails for up to six, three-day getaways, and informal instruction for anyone who wants the helm. Closed for summer 2026 until November.
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, whose ASA courses run on the charter boats as well as on a school-only Beneteau 38.
Featured Daysail Tampa Bay · Naples
Naples's longest-running sailing catamaran by its own account, a 53-foot Gold Coast cat carrying 44 passengers from the Naples City Dock since 1991. Daily sunset, shelling and sightseeing seat sails and private charters. The company's Sweet Tiki is a motor boat.
Tampa Bay · Bradenton Beach
Gulf-front beach rental on Anna Maria Island, family run for forty years and, by its own account, the only place on the island renting sailboats. Hobie Wave and Hobie Getaway catamarans by the hour or half day, first come, first served, with a short lesson for first-timers.