Come join us for an unforgettable cruise on one of our world-class sailing yachts. We serve clients seeking a unique sailing experience on the Chesapeake Bay.
Come sail with us on the Chesapeake Bay! As the largest estuary in the world, the Chesapeake Bay is stunningly beautiful, fed by countless navigable rivers and home to an abundance of wildlife.
Departing from West River Yacht Harbour, Classic Sail Charters offers Chesapeake Bay sailing adventures on a classic sailing yacht aboard Siena, a Dickerson 37.