Isla longs for a life beyond the real-estate business that her father runs. But career security is tempting. When she turns to her high-school sweetheart, Sayer, for advice, all he wants is for Isla to be happy.

The answer to her longing involves leaving Sayer behind in their New England sailboat town of Marblehead, Massachusetts, to pursue her future. With a heavy heart, Isla moves on from her past. But a stressful job in real estate, a broken marriage, and a family death leads her back to her childhood town, and to Sayer. Now Isla questions who she has become and who she wants to be, and if there was a place for Sayer all along.