The Gateway Clipper Fleet River Cruises (Wed., 8/27/25)

Pittsburgh Riverboat Cruises — Gateway Clipper Fleet. 

Sightseeing from the top deck of a Gateway Clipper ship on a dining cruise. (photo: Heather McCracken).

The Gateway Clipper Fleet has long been a crown jewel in the culture of Pittsburgh. Started by John E. Connelly with one riverboat in 1958, the outfit has grown and now boasts five vessels. The Gateway Clipper Fleet is still locally owned and operated by third generation owner, Terry Wirginis. Dining, sightseeing, and entertainment cruises make up the majority of the Fleet’s sailings. The riverboats are also available for private functions. Many a Pittsburgh young un’ got their first taste of river adventure on the former Good Ship Lollipop of the Fleet. Kid cruises are still a fun attraction for many and are much more elaborate these days with various themes and costumed performers. There are dinner cruises, sightseeing cruises, music cruises, and dance cruises. The Gateway Clipper Fleet has its own dock at Station Square and operates throughout the year. 350 W. Station Square Dr., Station Square. (R.H.)

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