The Clipper City was first built as a cargo schooner just prior to the Civil War, then rebuilt from the original plans, on loan from the Smithsonian Institution, and recently refurbished. The new, restored Clipper City, with a length of 160 feet and a height of 120 feet, can comfortably sail 144 people — the most of any passenger sailboat in the United States. With its sweeping deck, full bar, and eight sails, this majestic schooner and its attentive crew now sail daily from South Street Seaport, providing guests with a unique way to see Manhattan.

   The original 1854 Clipper City schooner came from the shipyard of Manitowoc, Wisconsin, a town soon nicknamed "Clipper City” because of its growing reputation for shipbuilding. The plans for Clipper City are in the permanent collection at the Smithsonian, and a replica cross-section of the boat is on permanent display at the Wisconsin Maritime Museum. In 1856, the U.S. Nautical Magazine & Naval Journal reported that Clipper City could sail from Chicago to Port Washington, Wisconsin, a full 115 miles, in just seven and a half hours. Built to haul lumber, she was enormously successful in her time. 

   Clipper City was decommissioned in 1890, but in 1984 naval architects DeJong & Lebet re-built her, with adaptations to meet modern safety requirements. The new Clipper City, a steel-hulled schooner carrying six fore-and-aft rigged sails and two square topsails on two steel masts, was operated as a Baltimore charter vessel for 20 years. She then fell into disrepair, but was recently acquired and extensively renovated. The ship that sails daily from Pier 17 on South Street has been carefully restored to match the beauty of her Civil War–era ancestor.