Devilment and Debauchery
Every self-respecting criminal needs a hideout, and pirates are no exception. Often pirate captains would make use of private coves, inlets, or remote islands and cays where a crew could careen their ship, make repairs, and replenish food and water stores if an opportunity arose. These forays, however, weren't necessarily fun and games. When a ship was careened, pirate crews were extremely vulnerable to attack by any passing ship, so pit stops such as these were a risky endeavor. Where then did pirates go when they needed to cut loose after months at sea?
Any good captain worth his salt knew that going ashore was not only beneficial to his crew's morale but could provide him useful information about potential victims and the riches their ships would be carrying. This meant paying a visit to a pirate-friendly port or town where pirates could abandon all semblance of morality and engage in whoring, gambling, and drunken debauchery.
Since the time of the ancient mariners there have been many ports that pirates frequented, but some of the more contemporary hideouts were more famous than others. Port Royal, Madagascar, Tortuga, Havana, Bermuda, and New Providence are just a few of the pirate havens that attracted the likes of even the most notorious pirates such as Blackbeard, Henry Morgan, and Black Bart. These areas served as safe harbors for black-hearted rogues, who were more than willing to partake of any luxury, cuisine, recreation, and wenching they could afford.