Jack and Max hire a delivery skipper, TJ, to bring her catamaran from Belize to Rye Harbor, New Hampshire. TJ takes on a mysterious woman as crew in Florida, but after she jumps ship in Gloucester, TJ enlists Jack's help for the final leg of the delivery. In Gloucester, TJ, an incorrigible womanizer, reconnects with a former lover and crew mate, and that chance meeting triggers a search for a black schooner from his past-along with the chance it affords for closure and revenge. His search takes him through Kennebunkport, Boothbay, and Camden, Maine, and finally to the Isles of Shoals, where TJ and Jack's friend Tom, the police chief of Rye Harbor, become targets of an unknown killer.