Panhandle · Pensacola
A 47-foot Leopard catamaran on Pensacola Bay, boarding at the Maritime Park docks downtown. Half- and full-day charters with paddleboards and kayaks aboard, swim calls at Deadman's Island and Fort McRae, an overnight to Orange Beach, and an ASA 114 course on the same boat.
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, with two queen staterooms sleeping four and room for up to two more. 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. 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. 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 and a sunset cruise, six guests at most, booked online. Captain Kirk has owned her 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 AJ's Seafood and Oyster Bar dock on Destin Harbor, then out East Pass into the Gulf with Captain Chris. Two- to four-hour private sails, sunset and fireworks cruises, time at the helm on request, and overnight trips year round.