Kelley Quinn is the owner of Nantucket's Winter Street Inn and the proud father of four, all of them grown and living in varying states of disarray. Patrick, the eldest, is a hedge fund manager with a guilty conscience. Kevin, a bartender, is secretly sleeping with a French housekeeper named Isabelle. Ava, a school teacher, is finally dating the perfect guy but can't get him to commit. But when Bart, the golden child and a recent Dartmouth graduate, announces that he has joined the Marines and is leaving for Afghanistan two days before Christmas, Mitzi is so distressed that she confesses to having an affair with a long-time guest at the Inn. As more secrets unravel and chaos ensues, it's up to Ava to piece together the holiday before everyone leaves, possibly forever.