Burnham and Root, Louis Sullivan, Frank Lloyd Wright and Ludwig Mies van der Rohe all created groundbreaking buildings in Chicago. And the world’s first skyscraper, the elegant terra-cotta and plate-glass Reliance Building, still stands at 1 West Washington Street. In addition to walking tours, the Chicago Architecture Foundation conducts tours by bus, “L” train, bike and even Segway. But my favorite is the River Cruise.

This 90-minute tour glides through the heart of downtown, exploring the Chicago River’s north and south branches, finishing where the river meets the lake near Navy Pier. Volunteer docents display impressive knowledge of Chicago history and the development of its architecture, and often interject amusingly opinionated commentary. Tours encompass famous landmarks such as the Spanish Revival Wrigley Building and the neo-Gothic Tribune Tower, as well as many lesser-known buildings with fascinating stories of their own. When the Standard Oil Building (now the Aon Center) was constructed in 1974, for example, gleaming Carrara marble clad the entire 83-story tower. Regrettably, the marble could not tolerate Chicago’s climate and cracked. The cost to reface the building in white granite exceeded that of the original construction!

Other companies offer architectural boat tours, but the Chicago Architecture Foundation has the best docents, and its craft provide more comfortable seating (as well as bars below deck). Buy tickets online in advance for weekends, and expect temperatures to be about 10 degrees cooler than on land.

CONTACT THE ANDREW HARPER TRAVEL OFFICE TO BOOK THIS CRUISE AS PART OF YOUR NEXT VACATION.