The Gateway Clipper Fleet, founded by John E. Connelly, is a Pittsburgh, Pennsylvania-based fleet of riverboats. The fleet cruises the three rivers of Pittsburgh - the Monongahela, Allegheny, and Ohio. The fleet is named after the city of Pittsburgh, which in earlier times was known as the "Gateway to the West". The original riverboat was Gateway Clipper, which set sail in 1958. By the mid-1960s, the fleet was composed of three craft, Gateway Clipper, Party Liner, and Good Ship Lollipop. Today there are five watercraft in the fleet: the 1,000-passenger Majestic; the 600-passenger Empress (formerly Party Liner); the 400-passenger Princess (formerly Keystone Belle); the 300-passenger Duchess (formerly Liberty Belle); and the 150-passenger Countess (formerly Good Ship Lollipop, previously known as City of Champions until 1982). Party Liner is a barge that is pushed by a towboat named the Empress II (formerly Gateway Liner).
The Gateway Clipper Fleet offers many types of cruises, from day trips for school groups to formal dinner cruises. Shuttle service to PNC Park and Heinz Field is available on days of Pittsburgh Pirates, Pittsburgh Steelers, and Pitt Panthers home games. The fleet is believed to be the largest inland riverboat fleet in the United States. The fleet formerly was moored at the Monongahela Wharf, but currently it is moored at Station Square.
In 2008 the Gateway Clipper Fleet celebrated its 50th year of sailing on the Three Rivers.