Panhandle · Pensacola Beach
Jolly Mon is a 27-foot American Mariner sloop, the boat this Pensacola Beach family business started with in 2011 and still its only sailboat. Two- to four-hour sailing, snorkelling and sunset tours from Pier One Marina. The rest of the Jolly fleet is powered tritoons.
The company’s own history starts with the sailboat: Jim and Cindy Bielinski founded Jolly Sailing on Pensacola Beach in 2011 with Jolly Mon, a 27-foot American Mariner, offering sailing, snorkelling and sunset tours, and everything else came afterwards. Jolly Mon sailing tours still run two to four hours, and she remains the only sailboat on the books.
What grew up around her is a powerboat operation, which is worth knowing before booking: Jolly’Ventures is a 26-foot tritoon for six, Jolly Roger a 24-foot tritoon for six, and Jolly Dolphin a 42-foot tritoon passenger vessel for 28, with a 49-passenger dolphin cruise catamaran under construction. The dolphin cruises and most of the snorkelling run on those, and a snorkelling trip may be assigned to either the sailboat or a powerboat, so it is worth asking which. The company also sells sunset and brunch cruises on Infinity through Blackwater Voyages. Departures are from Pier One Marina on Pensacola Beach Blvd, the same dock Condor Sailing Adventures works from.
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.