Dylan Scott, single but looking, is relaxing and reading on his Hinkley Bermuda 40 yacht, moored at Pier H-9 at Camachee Cove in St. Augustine. He is approached by a young woman, Heather McCabe, who asks Dylan for a lesson in how to sail. She was a fellow student but not a close friend at law school of Isla Whitney, who is a niece of Dylan. Heather slowly invites herself aboard and down into the cabin. After an increasingly pleasant discussion, she climbs the steps back to the cockpit and is struck by a rifle shot that kills her and sends her back against Dylan. He falls and is knocked unconscious. The local homicide sheriff, Steve Porter, arrives, and he and Dylan begin a close friendship that develops throughout the book. Steve introduces Dylan to his associate, Deputy Liz Cartwright, who a decade ago lost her husband and expected child to a drug lord while residing in Mexico. Liz and Dylan begin a relationship lasting only three dates. Liz goes missing. Unknown to Steve or Dylan, Liz goes to Kenya before returning to the U.S. and her birthplace, Martha's Vineyard. She contacts Dylan requesting him to come to Martha's Vineyard. He does. She explains to him why she left him. She prepares to shoot Dylan but at the last minutes kills herself. Dylan soon meets two other young women, Steve and Sarah Porter's friend Mandy Hill, and Tanya Green, cousin of a new friend who has arrived with his similar sailing yacht at the marina. The owner is Gray Herreshoff. Dylan arranges to meet each woman on successive nights and begins a relationship with each.