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.

As Stede tries to sell himself as the “Gentleman Pirate,” his men take a trip in hopes of ransoming the remaining hostage. While in the Republic of Pirates, Oluwande worries that Jim will cross paths with the notorious Spanish Jackie, as Blackbeard shocks Izzy by taking an interest in Stede.

While a feverish Stede flashes back to scenes of his marriage, Blackbeard experiences his own identity crisis. Jim suffers through questions from the overcurious crew. Then, with the Spanish approaching, two very different captains must each walk a mile in the other’s shoes.

When Blackbeard decides he wants to try his hand at playing aristocrat, Stede, Oluwande, and Frenchie assume new identities to accompany him to a fancy party. While Blackbeard relishes his alter-ego, Jeff, Oluwande, and Frenchie devise a scheme to get rich quick. Back on the ship, Izzy attempts to punish Lucius.

Inspired by Blackbeard’s words of wisdom, Stede enlists the Revenge crew to help him intimidate an incoming merchant ship. After Izzy confronts him about his growing attachment to Stede, Blackbeard struggles to do what must be done. Lucius’ flesh wound spirals out of control.