Panhandle · Niceville
Bareboat rentals and crewed sails from Bluewater Bay Marina on Choctawhatchee Bay. J/80s by the day, a Beneteau 331 and a Jeanneau 389 by the day or up to three nights aboard, for skippers with ASA 103 or equivalent; captained sunset, dolphin and Crab Island trips for up to six.
The rental fleet is the school’s fleet: J/80 sportboats by the day, and a Beneteau 331 and a Jeanneau 389 by the day or on two-, three- and four-day overnight packages, with dockage, fuel, pump-out and cleaning included. Every rental starts with a checkout briefing aboard that covers the boat’s systems, communications, safety gear, rigging and trip planning. Qualified skippers hold ASA 103 from any accredited school, an equivalent US Sailing or RYA certificate, or can show demonstrated experience on similar boats, and the operator says its own graduates use the daily rentals to build sea time on boats they already know.
The crewed side runs private trips for up to six on the Jeanneau 389, the Beneteau 331, a Catalina 320 or an Admiral 40 catamaran: sunset sails, afternoon dolphin runs, and the sail down the bay to Crab Island off Destin. The marina sits in Rocky Bayou on the north shore, so a rental gets sheltered water for the first mile and the whole of Choctawhatchee Bay after that, with Destin’s East Pass to the Gulf at the far end for a crew with the experience to use it. The ASA school that shares the docks has its own listing.
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.