This painting depicts the Sappho, owned by Vice Commodore William P. Douglas and the Vesta, owned by Pierre Lorillard, in a match race in the upper bay of New York. Castle Garden is on the tip of Manhattan, on the left, and Castle William on Governors island, is on the right. James Buttersworth included the APPHO IN SOME OF HIS MORE THRILLING ACTION SCENES OF YACHT RACING. ANOTHER VERSION OF THE SAPPHO AND THE DAUNTLESS IS ILLUSTRATED AND DISCUSSED IN RUDOLPH J. SCHAEFER, J.E. BUTTERSWORTH, 19TH CENTURY MARINE PAINTER, (MYSTIC SEAPORT, CONNECTICUT, 1975), P. 172, PL. XVIII. ALSO SEE PLATE XVII, A RACE BETWEEN THE MAJIC AND THE GRACIE WITH THE SAME BACKGROUND.