After uprooting his life in search of adventure, aristocrat-turned-pirate-captain Stede Bonnet must go to new lengths to tame the mutinous motley crew of his ship, the Revenge. But when his efforts to impress the boisterous buccaneers lead to a raid on a vessel with ties to his former life, Stede is left to question whether he's tough enough for the high seas.

When the Revenge runs aground, Stede attempts to assuage his guilt over recent events by encouraging his men to treat the island detour as a vacation. On the hunt for missing hostages, Stede, Oluwande, and Black Pete encounter some new faces, while Lucius stumbles upon Jim's secret.

Stede Bonnet abandons his life of privilege to become a pirate in the early 18th century.