The Miltons are a powerful old New York family - the kind of family that used to run the world. And in 1935, they still do. Kitty and Ogden Milton seem to have it all- an elegant apartment on the Upper East Side, two beautiful little boys, a love everyone envies. When a tragedy befalls them, Ogden comforts Kitty the only way he knows how - they go sailing, picnic on a small island off the coast of Maine, and buy it.
For generations the Miltons of Crockett Island revel in a place that is entirely their own. But it's 1959, and the world is changing- Ogden's firm hire a Jewish man, Len Levy, who earns the admiration of not only his boss, but his boss's beautiful young daughter. When Len and his African-American friend visit the island, the Miltons' principles and prejudices are challenged like never before.
At the dawn of the twenty-first century, the family money has run dry, and the island is up for sale. Returning for one last visit, Kitty's granddaughter uncovers disturbing evidence about her family's wealth - and realizes she is on the verge of finally understanding the silences that seemed to hover just below the surface of her family all her life.