Isaac is a talented 18th-century artist but has no money to start a life with his love, Alice. When a rich captain hires him to come along on his ship and document their voyages, Isaac takes the chance. Unfortunately, Isaac becomes the newest recruit on a pirate ship. He embarks upon a series of adventures that range in tone from hilarious to dark and see him all the way to the Caribbean and the icy North. After years away, he returns home to his much older father. But after a life fueled by robbery, drinking, and women, his search for Alice and a clean life proves elusive.