The academy utilizes its extensive waterfront facilities to house Tabor's 92' schooner 'S.S.V. Tabor Boy'. The Tabor Boy is one of the most famous and recognizable features of the school. The roots of the program were founded in 1917 when then headmaster W.H. Lillard arranged to borrow two cutters from the U.S. Navy to develop the academy's nautical programs. In 1925, "The Tabor Boy Trust" was formed to raise funds to purchase an 88' schooner for the school's use. In 1933, Headmaster Lillard, Captain Lewis and 18 students sailed the Tabor Boy up the Hudson River, through the New York State Canal System and down the Great Lakes to show the Tabor Boy off in an eight-week exhibition at the World's Fair in Chicago.