Equal parts boat and buildings, this river cruise gives you a from-the-water perspective of Chicago skyline and up-close views of its most iconic structures. Board an open-roofed vessel and float with the current as an architecture expert shares the fascinating history behind the Windy City's most renowned buildings.

Hop onto your vessel at Navy Pier, steer toward the Chicago River—a 156-mile (251-km) system of streams and canals—and cut directly through the heart of the city. Once vital to the early shipping success of Chicago, this winding body of water now offers the perfect platform for admiring its surrounding architectural marvels.

Your cruise takes you past more than 40 points of interest, including the Tribune Tower—a neo-Gothic building constructed in 1925—and the Willis Tower, the second-tallest building in the United States. Crane your neck up at the John Hancock Tower, a skyscraper equipped with an impressive observation deck perched 1,000 feet (304 m) high.

As you glide through the city, a knowledgeable guide and architecture buff shares stories about the distinctive designs, striking construction, and steel-and-cement feats created by world-famous architects like Mies van der Rohe, Helmut Jahn, and Louis Skidmore. From the IBM and USG buildings to the Fulton House and Citicorp Center, this tour is the perfect snapshot of Chicago's architectural gems.