This is the story of Annie, a girl who grew up on Oak Island, a beach town in North Carolina. As a young teen, her love of sailing and boating led to important skills needed later in life. Many challenges came her way and the way she dealt with them defined her character. A mobster client she once had as a young lawyer came back to test her resilience. Piracy, gambling, and adventure all cross her path and complicate her desire to re-unite with a boy she met at summer camp years before. Follow her journeys alonng the Atlantic coast and the Intracoastal Waterway, the ICW.