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. Three boats, a Morgan 44, a Catalina 355 and a Leopard 45 catamaran, out for one to four hours with six aboard.
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 by Cavu, a 2013 Catalina 355, and Wind Therapy, a 2019 Leopard 45 catamaran.
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. The same fleet runs ASA instruction one week and bareboat charter the next.
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.