Tampa Bay · Holmes Beach
Capt. Kit Baxter sails Flip Flops, a Maine Cat 30 catamaran, out of Holmes Beach on Anna Maria Island, six guests at most. Public sails go with two aboard, private sails need three spots. Sunset and day sails on the bay, and four- to six-hour runs to Passage Key and Egmont Key.
The boat is a Maine Cat 30, a 30-foot catamaran, and the Coast Guard cap is six passengers, which makes every trip small by default. A public sail goes out with a minimum of two and other guests may join; a private sail is the same trip with the boat to yourself. Sunset and day sails run two and a half hours on the bay, with the sunset departure moving through the year to leave roughly two hours before the sun goes down. Bottled water and parking are included and guests bring their own food and drink, red wine excepted.
The longer trips are the island runs. Passage Key is four hours, an hour’s sail out, two hours anchored to swim and shell, an hour back; the operator is direct about the two things to know, that it is a bird sanctuary so you stay in the water rather than walking up on it, that it is well known for being clothing optional, and that since the 2024 hurricanes it is a sandbar rather than a key. Egmont Key is five hours, with time ashore on the north end to see the lighthouse, the gopher tortoises and the ruins of Fort Dade, the southern end being closed as a bird sanctuary. Booking is online.
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.