We are Eastern Shore Sailing and the Schooner Windsong! A family owned and operated sailing charter company based out of Cape Charles VA, we specialize in 2-hour day sailing trips and private sunset charters, as well as small group and private sailing lessons.
Join us today and experience your own unique sailing adventure on the Chesapeake Bay aboard the beautiful Schooner Windsong. Relax with a beer or a glass of wine as we sail the smooth waters of the Chesapeake Bay or take a hands on approach and help the crew set the sails and helm the boat.
We can also offer full day charters that may include options for swimming and lunch. Or let us customize your special occasion by offering assistance with local catering options for birthdays, anniversaries, and weddings (we’ve had one on board)!
