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.
Island Time Sailing works two sailing catamarans out of North Lagoon Drive on Grand Lagoon. Island Time is the 50-footer, carrying up to 65 with shade on the lower deck, restrooms and a snack and drink bar; Island Time II, 53 feet long and 27 wide, was built in 2017 by the yard that built the first boat. Both fly the company name on the boom cover.
The signature trip is the three-hour Shell Island Snorkel & Sail: out through St. Andrews Bay and the jetties, dolphins on the way, then snorkel gear, paddleboards and a water slide at the island. The two-hour Sunset Dolphin Sail runs the same waters at the end of the day, with beer, wine and the boat’s rum punch at the bar. Both are sold by the seat through the online booking calendar.
The company also rents pontoons and jet skis, and sells private charters on The Islander, a 49-passenger boat the site does not describe as a sailboat. For a trip under sail, book one of the two catamarans.
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.