In 1962, coed Heddy Winsome leaves her hardscrabble Irish Brooklyn neighborhood behind and ferries to glamorous Martha's Vineyard to nanny for one of the wealthiest families on the island. But as she grows enamored with the alluring and seemingly perfect young couple and chases after their two mischievous children, Heddy discovers that her academic scholarship at Wellesley has been revoked, putting her entire future at risk. Determined to find her place in the couple's wealthy social circles, Heddy nurtures a romance with the hip surfer down the beach while wondering if the better man for her might be a quiet, studious college boy instead. But no one she meets on the summer island—socialite, starlet, or housekeeper—is as picture-perfect as they seem, and she quickly learns that the right last name and a house in a tony zip-code may guarantee privilege, but that rarely equals happiness.