Brent Bishop lives in an affluent home in contemporary Chicago. His dad has been steadily moving up in the corporate world and can now bankroll the lifestyle Brent's parents want, a private school for Brent, an expensive house, cars, all the "right" things to make life happy. There is an inner restlessness, dissatisfaction, and feeling of isolation in Brent that his dad's money cannot fix.

Whirligig moves Brent from Chicago, via Greyhound bus, on a circumventing journey of the United States: Washington, California, Florida, and Maine.

Brent meets obnoxious and unsavory people on the bus and in cheap hotels, but makes a friend in a youth hostel in San Diego who gives him a copy of Two Years before the Mast. The camaraderie enjoyed by the transient residents of the hostel attracts Brent. He begins looking at his fellow travelers differently. The jostling bus ride around the country...