Tampa Bay · St. Petersburg
Captained sails on Tampa Bay from the Harborage Marina, run by a couple who cruised the Caribbean aboard the boat that is now the fleet's flagship. A Morgan 44 and a Leopard 45 catamaran out for one to four hours with six aboard, plus private sailing lessons on a Catalina 355.
The flagship has a history that predates the charter business. Satori, a 1989 Morgan 44 center cockpit, carried owners Nick and Kelly Johnson around the Caribbean and was the subject of their Sailing Satori video channel before they came ashore in Tampa Bay to raise a family and put the boat to work. She is joined on the charter side by Wind Therapy, a 2019 Leopard 45 catamaran; Cavu, a Catalina 355, now serves as a training platform. Since mid-2026 the company also sells private and small-group sailing lessons, capped at four students, including practical training toward NauticEd’s Bareboat Charter Master and SLC.
Every trip is captained and capped at six guests by the Coast Guard certificate, in one, two, three and four-hour blocks including sunset. The sailing stays in Tampa Bay, generally between downtown St. Petersburg and the Skyway Bridge and within a few miles of shore, so it is protected water and a short sail from the slips.
St. Petersburg lost most of its charter fleet in 2026, when Waypoints closed the base it ran from the Vinoy and the SailTime franchise at the Harborage folded. This is the sailing fleet working the downtown waterfront now.
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.