Jolly Mon Sailing Tours

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 Jolly Mon, 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 Jolly Mon is certified for 6 passengers, most comfortable for families or smaller adult groups. Cruises range from 2 to 8 hours and may include snorkeling and other activities, in season. She has a unique design that allows for anchoring in shallow waters, for a beach stop, swim break or snorkeling fun on select longer tours. There is also a full sized cabin with galley and restroom below. 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!

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 and many other forms of wildlife on our sailing excursions.

Skip the crowds and join us for a tranquil and personalized experience. Create unforgettable memories aboard the deck of this awesome sailboat!