Tampa Bay · Captiva
The one sailboat rental on Sanibel or Captiva as of September 2026. Fourteen-foot Hobie Waves from the shop on Andy Rosse Lane, the Captiva village street that ends on the Gulf beach, by the hour up to a full day and reservable in person, online or by phone.
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.