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Jolly Mon Sailing Tours

Quick Details

Private Cruise

Set Sail in Pensacola!

Sailing in Pensacola has been a tradition since 1559, when Don Tristan De Luna of Spain landed on the shores of Pensacola Bay, marking the first European settlement in mainland America.

The waters of Pensacola Bay and Santa Rosa Sound are renowned for sailing and cruising, featuring steady afternoon sea breezes, plenty of depth, and easy anchorages.

On the Jollymon, our sporty custom 27’ American Mariner sailboat, you can experience a sailing adventure just like the early explorers. Your Captain will be happy to show you the ropes, and even let you steer the boat, or you can just sit back, relax, and enjoy the scenery. The Jollymon is certified for 6 passengers, most comfortable for families or smaller adult groups. Cruises range from 2 to 4 hours and may include snorkeling, in season. This boat is an excellent choice for private cruises, at an affordable rate. Sailing is a wonderful experience that is relaxing and exciting at the same time.

We also offer premium sailing adventures through our affiliate, aboard the S/V Resolute, a glorious 42’Vagabond Ketch. Several options are available aboard the Resolute, from 2 hours, to a full day! Enjoy a romantic sunset sail, day sail, Gulf sailing adventure, dinner cruise or custom cruise. Private and shared trips available.

Sailing with dolphins on Northwest Florida’s Gulf Coast is a unique experience. Wild dolphins seem naturally attracted to sailboats, often swimming alongside us, crossing our wake, playing, and feeding nearby. Though we cannot always guarantee a sighting, we do cross paths with dolphins on many sailing excursions.

Skip the crowds and join us for a relaxing and personalized experience. Create unforgettable memories aboard the deck of one of these classic sailing vessels!