The "Winged Arrow," the ship on the right, and the "Southern Cross," left, were built in Boston in the early 1850s, during the glory days of the Massachusetts maritime industry. In 1853 their owner, Benjamin K. Hough, Jr., of Gloucester, Massachusetts, commissioned Fitz Henry Lane to make this portrait of his new vessels. Hough was engaged in an import–export business that, among other ventures, supplied Brazilian rosewood to piano manufacturers. The ships pictured here sailed principally between Boston, California, and the Far East. The "Winged Arrow" was a particularly fast ship, making the voyage around the Horn to the West Coast in noteworthy time. She was sold to a Russian fur-trading company in 1868. The "Southern Cross" was burned by the Confederate forces in 1863.
Lane’s training as a lithographer and his native Gloucesterman's knowledge of nautical science are both evident in the precise rendering of ship’s anatomy seen here. The shadows cast on the sails and the pink-tinged silhouette of the Boston skyline beneath the bright, blustery New England sky enliven this painting and make it far more than an accurate depiction of two ships.