Your adventure starts here! The Sailing Academy is the closest sailing school on the Chesapeake Bay to the Washington, D.C., Beltway, blending prime conditions with easy access. Family owned and operated; our teaching method is closer to on-the-water coaching rather than simply taking a class. Our goal is to equip learners with both proficiency and confidence so they can achieve their own sailing dreams—whether that is to cruise the Chesapeake Bay or to eventually cross oceans.