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 tradition continues today, as the area is training headquarters for the New York Yacht Club America's Cup team sailing vessel, American Magic. 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, if you feel adventurous! Sailing is a wonderful experience that is relaxing and exciting at the same time. Sit back, relax and enjoy the scenery, along with a cold drink or two! Complimentary drinks, including beer and wine, are offered on this cruise for guests of legal drinking age. 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 other sealife often on sailing excursions.