Everleigh “Lee” Farrows thinks she finally has life all figured out: a handsome fiancé named Roland, a trust in her name, and a house in Bronxville waiting for her to fill it with three adorable children. That is, until Roland brings her out to the Hamptons for a summer that will change everything. Most women could only dream of the engagement present Roland unexpectedly bestows on Lee --- a beachside hotel on the prized Gin Lane --- but Lee’s delight is clouded by unpleasant memories of another hotel, the Plaza, where she grew up in the shadow of her mother’s mental illness. When tragedy strikes on the hotel’s opening weekend, the cracks in Lee’s picture-perfect future slowly begin to reveal themselves.

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couple and chases after their two mischievous children, Heddy discovers that her academic scholarship at Wellesley has been revoked, putting her entire future at risk.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 is as picture-perfect as they seem.