Select Page

Chesapeake Bay Sailing Charters


The Classic Yacht Lady Patty

If varnished teak, polished bronze and a glimpse back in time at the golden age of American yacht racing appeals to you then check out the classic Lady Patty. She was built in 1935 right here on the Bay. She raced in many notable ocean races including the St Petersburg to Havana Race and the Transpac from San Fran to Hawaii. Now she treats her guests to a sailing experience on the Chesapeake Bay that they will remember for a lifetime. Excursions depart three times most days from Tilghman Island for the Chesapeake Bay.


R Rourke The Skipjack Rebecca T Ruark

If you are an experienced sailor or hoping to have your first experience under sail, you have come to the right place for Chesapeake Bay sailing charters. Tilghman island is rich with the history of boat building, sail driven fishing vessels and in more recent years, sailing yachts and pleasure boats.For a look at a 100+ year old working skipjack, or sail-driven, Chesapeake Bay oyster dredge boat you should look no further than Dogwood Harbor. There you will find the Rebecca T. Ruark and her Captain Wade Murphy Jr. You will be treated to a first hand history of Tilghman Island, the local fisheries and the Rebecca T. Ruark by a third generation Tilghmaner, all the while under sail.