"Port Royal" Enamel Mug

Port Royal provided a safe harbor initially for privateers and subsequently for pirates plying the shipping lanes to and from Spain and Panama. Buccaneers found Port Royal appealing for several reasons. Its proximity to trade routes allowed them easy access to prey, but the most important advantage was the port's proximity to several of the only safe passages or straits giving access to the Spanish Main from the Atlantic. The harbor was large enough to accommodate their ships and provided a place to careen and repair these vessels. It was also ideally situated for launching raids on Spanish settlements. From Port Royal, Christopher Myngs sacked Campeche and Henry Morgan attacked Panama, Portobello, and Maracaibo. Additionally, buccaneers Roche Brasiliano, John Davis and Edward Mansvelt used Port Royal as a base of operations.

Since the English lacked sufficient troops to prevent either the Spanish or French from seizing it, the Jamaican governors eventually turned to the pirates to defend the city. By the 1660s the city had, for some, become a pirate utopia and had gained a reputation as the "Sodom of the New World", where most residents were pirates, cutthroats, or prostitutes. When Charles Leslie wrote his history of Jamaica, he included a description of the pirates of Port Royal:

Wine and women drained their wealth to such a degree that [...] some of them became reduced to beggary. They have been known to spend 2 or 3,000 pieces of eight in one night; and one gave a strumpet 500 to see her naked. They used to buy a pipe of wine, place it in the street, and oblige everyone that passed to drink.