Serving Annapolis since 2009, Classic Sail Charters provides exceptional hand-on or leisurely sailing experiences for private parties up to 6 passengers – your choice. Licentia, our 42 foot Catalina is always clean, thoroughly maintained, and a joy to sail. Our captains are all highly experienced professionals licensed by the US Coast Guard, and certified as sailing instructors to safely and clearly provide you with whatever level of hands-on participation you imagine.
Discover Your Freedom!
Memorable Adventures for Adventure Seekers
Our Amazing Team
Our expert captains will ensure your safe, relaxed, and memorable wind-driven time on the water.
Captain Tony Ireland was racing small sailboats on the Long Island Sound in the 60s, and somehow, after years of professional corporate experience, he found his way back and has been sailing blue water cruisers for the past two decades, including several offshore races, numerous yacht deliveries, and chartered cruises on the Chesapeake and Biscayne Bays, as well as the Caribbean and the Florida Keys. He is a USCG licensed captain, an ASA certified instructor, and currently teaches captain’s license courses during the off-season.
Captain Nate Hesse has sailed the waters of Maine, Cuba, British Columbia and the Adriatic Sea, but is always drawn back to the maritime culture of the Chesapeake Bay. He has captained traditional boats for outdoor education and environmental organizations on the Chesapeake Bay and Washington State, led youth sailing programs, and captained various private sailing yachts. He is a USCG licensed captain, and an US Sailing certified instructor.