Whitehead recreates for us 1980's Sag Harbor, a summer retreat for upper-middle-class New York African American families, a tight-knit social circle whose interactions fall primarily between Memorial Day and Labor Day. Fifteen-year-old Benji offers us his eyes into this world. Back at home, Benji and his brother Reggie play the role of the token black students in their schools, which makes their sudden immersion into black culture each year at Sag Harbor more of an adjustment than it is for most. Benji is a self-described dork though he takes pains to hide his more embarrassing character flaws from his Sag Harbor friends, such as his penchant for horror films. Benji considers himself the boy who is always one step behind everyone else, following the trends once they've already been set, figuring out the appropriate social actions long after everyone else seems to have magically intuited them.
The summer of 1985 is one of typical beach antics and newfound freedoms. Benji's parents are strictly weekenders, leaving him and Reggie to reign the house Monday through Friday. As some of the boys in his crew start to drive and receive generous and faithful gifts from their parents in the form of automobiles, a whole new type of adventure opens up to these vacationing teenagers. And Benji enters the world of work in the form of serving frozen ice cream treats to ungrateful beach-goers.
Sag Harbor stands as an eloquent testament to growing up, to savoring those dwindling summers before adulthood sets in, to the moments when you think you have it all figured out and have entered a new realm of cool, only to make a complete and utter fool of yourself. Whitehead's novel is a humorous and vivid account of one confused black American teenager's coming-of-age story, complete with elaborate depictions of the disdained Hamptonites, the tacky boat tourists from Connecticut, the mysterious girls that offer Benji just a glimmer of hope of fulling graduating from childhood, and the African American professionals who call Sag Harbor their summer home.