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.
The boat is the reason to look twice. The Condor 40 was designed by Phil Herting and Mick Price, the co-founders of Condor Limited, and built in Annapolis from 1985 to 1991 as an ocean racer; twenty-one exist, and the first was named Endangered Species. Dare II is 40 feet long and 28 feet wide across her three hulls, and the operator’s pitch, that a trimaran sails flat and fast enough to spare the seasick, is the design working as intended. Michael “Captain” Kirk has owned her since 2002 and once crossed the Atlantic nonstop, 35 days and 5,800 miles, on the sister Condor Thunderbird; he holds a Coast Guard 100-ton master’s license.
Cruises are two hours, three times a day: an 11am and a 2pm sail with dolphin watching, and a sunset cruise. The boat takes six, and guests ride the side decks and the bows, feet in the water if they like, under the shade of the mainsail. Pier One Marina is the second building on the right after the toll booths onto the beach, a three-story mustard-colored block beside Aloha Wine and Liquor; marina parking is limited and there is more across the way.
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.
Daysail Panhandle · Panama City Beach
Two sailing catamarans, the 50-foot Island Time and the 53-foot Island Time II, out of Grand Lagoon in Panama City Beach. A three-hour snorkel sail to Shell Island with gear and paddleboards aboard, and a two-hour sunset dolphin sail, both sold by the seat.