Gateway Clipper Fleet | 529 followers on LinkedIn. A symbol of Pittsburgh's river renaissance, the Gateway Clipper Fleet has grown from a one boat, 100 passenger operation to the five boat, 1500 passenger fleet of today. Sailing from the Southern Bank of the Monongahela River at Historic Station Square, the Gateway Clipper Fleet sails all year and offers a wide variety of dining, sightseeing, and entertainment cruises. We sail year round and specialize in both public and private cruises.