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, rated for 78 but capped at 65 so there is room to move, with shade on the lower deck, two 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.
Its sister company, Lagoon Pontoons, rents pontoons and jet skis from the same dock, and the site sells private charters and 90-minute dolphin cruises on The Islander, a 49-passenger catamaran it never describes as sailing. For a trip under sail, book one of the two catamarans with masts; three captains, Clay, Heath and Christo, share them.
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, a sunset cruise and Blue Angels practice cruises, six guests at most. Captain Kirk's 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 Destin Harbor docks at 600 Harbor Blvd and goes out East Pass into the Gulf with Captain Chris. Two- to four-hour private sails, sail-and-swim trips, sunset and fireworks cruises, whole days, and overnights by arrangement.