Tampa Bay · St. Petersburg
Between boats. Hawkeye, the 47-foot sailboat behind these two-hour sunset sails from downtown St. Petersburg, was sold in June 2026, and the sails are on hold until the company finds another vessel.
Tampa Bay Sunset Sail is between boats. Hawkeye, the 47-foot sailboat it sailed, was sold in June 2026, and the business is on hold while the company looks for another vessel (as of October 2026).
The trip it ran was a single well-defined thing: two hours at the end of the day on Tampa Bay, leaving downtown St. Petersburg, out past the St. Pete Pier and along the waterfront while the skyline lit up. Guests were capped at six whether the sail was shared with other passengers or booked private, which was the operator’s argument for it over a larger boat. The company said it spent as much of the evening as it could under sail with the engine off, and that dolphins usually turned up.
The business trades as Time and Tide Captain Services, LLC. Capt. Andy is a St. Petersburg-area native and a former high school teacher, holds a Coast Guard 50-ton master’s licence with a sailing endorsement, and is a certified instructor with American Sailing, Offshore Sailing School, US Sailing and NauticEd; Capt. Wayne holds a 100-ton licence and has been sailing more than fifty years.
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.