The village of Sag Harbor is on the bay side (northern part) of the South Fork of the tip of Long Island, and an old whaling port where several African-American families have bought property over many years despite the area's history of segregation.

At the start of summer vacation, teenage brothers Benji and Reggie Cooper escape their majority white preparatory academy in Manhattan for the Sag Harbor Hills, Azurest, and Ninevah Beach Subdivisions Historic District.

Like most well-to-do kids at their families' beach houses during the summer, most of the teens in Sag Harbor go almost the entire season with virtually no contact from their parents, including allowances.

With the lack of parental supervision, the boys manage to get into trouble, like being stuck out of town when their car won't start, and having a BB gun fight that nearly takes out an[who?]

[1] In the wake of the election of President Barack Obama and the success of other African Americans in the national spotlight, this story of a wealthy black teenager depicts a situation that was anachronistic for its 1985 setting.