According to pirate legend, some of these pioneering thieves even set up a utopian colony called Libertalia, where they mingled with native women and organized a democratic government. Beginning in the late 17th century, well-armed bands of freebooters used the African island of Madagascar as a base of operations for raids on European and Asian shipping. Peg-legged pirates and swashbuckling sea captains are usually associated with the Caribbean, but many of the most successful buccaneers plied their trade in the Indian Ocean. Among countless others, buccaneers like the ruthless Charles Vane and the flamboyant “Calico” Jack Rackham would eventually meet their end in Port Royal. ![]() By 1720, the town had begun to clean up its act and its “Gallows Point” became a notorious site for pirate hangings. But when these raiders began indiscriminately plundering shipping traffic in the Caribbean, Port Royal’s colonial authorities were finally stirred into action. Even after the age of privateering had ended, the so-called “wickedest city on Earth” continued to serve as a retreat for a new brand of lawless, freelance pirates. Contemporary accounts describe a seamy harbor overrun with gambling, prostitution and drink, where hard-living mariners often squandered thousands of Spanish reals in a single night. Port Royal prospered on the back of its pirate economy, and by the 1660s its streets were lined with taverns and brothels eager to cater to the whims of young buccaneers flush with Spanish loot.
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