Schooner Windsong is a 47-foot Tancook Schooner designed by Ray Stevens of Nova Scotia. She was built by Guy H. Asbury between 1954 and 1960 in Yarmouth, Nova Scotia. Much of her life was spent in New York; both around Long Island, and on Lake Ontario. Throughout her life she has been named Pleiades, Dream, John A. Noble, Chasseur, and Sara B. Schooner Windsong is now based out of Cape Charles, Virginia, offering sailing charters for up to 6 people on the waters of the Chesapeake Bay.

Windsong is racing on behalf of the Vessel Disposal and Reuse Foundation. This Virginia nonprofit's mission is to help waterways achieve sustainable health through removal of abandoned and derelict vessels, public outreach, and education. VDRF has removed 25 abandoned and derelict vessels from the waters of Hampton Roads in less than 2 years as an organization. Their hard work and commitment to the health of our waterways has an immediate and lasting effect. In 2022 Schooner Windsong raised $2191.15 for VDRF, and they are aiming for a goal of $5000 in 2023!