Panhandle · Pensacola
A 47-foot Leopard catamaran on Pensacola Bay, boarding at the Maritime Park docks. Half- and full-day charters with paddleboards and kayaks aboard, swim calls at Deadman's Island and Fort McRae, an overnight to Orange Beach, ASA 114 aboard and basic lessons on Hunter dinghies.
Southern Star is a 47-foot Leopard catamaran, and the charter is built around stopping rather than just sailing: every package comes with inflatable paddleboards, a double kayak, a floating hangout platform, floating chairs and sea saddles, and the usual course runs across Pensacola Bay to a swim call at Deadman’s Island or Fort McRae by Pensacola Pass. A half day is three hours and a full day six hours, with catering available and a discount for veterans. Two Pensacola specialities ride on top of the ordinary sail: the Blue Angels practice shows on Tuesday and Wednesday mornings, and the American Magic America’s Cup team, which has used Pensacola’s water as a winter training base since 2021 and can sometimes be chased down the bay.
The overnight product leaves the state. Boats sail from Pensacola Bay to Sand Island and Pirates Cove and tie up for the night on the dock at The Wharf in Orange Beach, Alabama, beside the amphitheatre, fully catered both days, priced for two queen staterooms at two people each, with up to four staterooms available for a party of eight. The company also sells sailing instruction on the same catamaran, a two-day ASA 114 cruising-catamaran course at five hours a day, taught as private instruction for one crew by an American Sailing instructor, per the operator, and basic monohull lessons on a Hunter 146 (four crew) and a Hunter 235 (six crew), private, two hours minimum. Capt. James and Ingrid own and run the business, which is Navy veteran owned, and have sailed the Aegean, the Gulf coast and the Bahamas with their three boys; Capt. Linda, an American Sailing instructor and Coast Guard master who has skippered cruising catamarans in the British Virgin Islands, also teaches, and Capt. George handles the kayak and paddleboard excursions ashore. Boarding is at the public docks on the west side of Blue Wahoo Stadium in Maritime Park.
Daysail Panhandle · Pensacola Beach
Two-hour sails from Pier One Marina on Pensacola Beach aboard Dare II, a Condor 40 trimaran, one of twenty-one built in Annapolis from 1985 to 1991. Daily 11am and 2pm sails, a sunset cruise and Blue Angels practice cruises, six guests at most. Captain Kirk's since 2002.
Crewed Panhandle · Fort Walton Beach
No trips for the rest of 2026 after hurricane damage in the area; the owners plan to resume in March 2027. Private crewed catamaran daysails on a Stiletto 27 from Adventure Marina on Okaloosa Island, with Crab Island, sunset and snorkel runs for up to six guests.
Crewed Panhandle · Destin
Space Dancer, a 45-foot Beneteau sloop, leaves the Destin Harbor docks at 600 Harbor Blvd and goes out East Pass into the Gulf with Captain Chris. Two- to four-hour private sails, sail-and-swim trips, sunset and fireworks cruises, whole days, and overnights by arrangement.