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. Sailing, snorkelling and sunset tours of two to eight hours from Pensacola Beach Boulevard. The rest of the Jolly fleet is powered.
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 run two to eight hours, up to a full-day sail to Sand Island with lunch and snorkel gear aboard, and she remains the only sailboat on the books.
What grew up around her is a powerboat operation, which is worth knowing before booking: three tritoons (two six-passenger boats and a 42-foot passenger vessel) and, since summer 2024, a custom-built motor catamaran for the dolphin cruises that the site variously gives as 38 or 40 feet and up to 49 passengers. 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 655 Pensacola Beach Blvd, the Pier One Marina address Condor Sailing Adventures also works from; the confirmation email carries the directions.
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.