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.
Destin Sailing Adventures is running no trips for the rest of 2026 because of recent hurricane damage in the area, and the owners plan to resume operations in March 2027 (as of October 2026).
The boat is a Stiletto 27, a light performance racing catamaran, which makes this the sporty option among the pontoon armada headed to Crab Island: guests ride the trampoline nets over the water while the boat actually sails. Trips are private, up to six guests, bring-your-own cooler contents welcome, with ice, a head, and a sound system aboard.
The crew is the provenance here. Captain Kip has fifteen years of sailing and racing behind him, including a 2023 Hobie 33 national title as bowman at Charleston Race Week, and runs the boat with co-owner Elizabeth, his racing partner; guest reviews name them both. The trip lineup runs three-to-nine-hour Crab Island adventures, two-and-three-hour sunset sails, and snorkel, dolphin, sunrise, and fireworks variants across Destin East Pass, Santa Rosa Sound, and Choctawhatchee Bay.
One naming note: despite the brand, the dock is Adventure Marina on Okaloosa Island in Fort Walton Beach, a few minutes west of Destin proper. Booking runs through the operator’s site.
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 · 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.