In Chesapeake, the Turlock family, descended from Timothy Turlock, reveal the struggles of a family descended from a common thief, sentenced to hanging because he has been caught stealing more than once, most recently having stolen some bread. He is spared because of his mother's pleas and Timothy Turlock's punishment is commuted to working in service in Virginia, USA. He will be required to do "seven years of just and fair labor" on a tobacco plantation in Virginia but will be "banished" from England for ever.

Each chapter in Chesapeake begins with a voyage and Timothy's voyage in  1636 takes him to marsh land, a "wretched spot," because the ship owner, Mr Barstowe cannot find a buyer for him. The buyers have realized that Timothy is probably a trouble maker and Mr Barstowe has to resort to taking Timothy further down river for a sale. He even sells him for half a batch of tobacco leaves as the family, who eventually take him are desperate for help but they also see Timothy's scars from the many lashings. They take him in because Mrs Janney recognizes his "spirit."

Timothy eventually escapes from the Janneys, having had a taste of what life could be like "across the bay." He is confronted by a group of Indians and learns many survival tips from them.