Pirates of Port Royal, Jamaica: A Pirate's Haven

Port Royal: The Wickedest City in the New World

Port Royal in the late 1600s was infamous as the “pirate utopia” of the Caribbean – a booming port where wealth and debauchery flowed in equal measure. After England seized Jamaica in 1655, the town’s strategic harbor quickly became a magnet for privateers and buccaneers. Its location was ideal: close to busy shipping lanes and the Spanish Main, with a deep natural harbor and nearby shallow waters perfect for careening pirate ships.

Early governors like Edward D’Oyley actively invited the Brethren of the Coast – a fraternity of pirates – to make Port Royal their home base, even granting them legal commissions (letters of marque) to attack Spanish targets. In effect, Jamaica’s authorities turned a blind eye to piracy as long as Spain was the victim, enabling Port Royal’s rapid growth and notoriety.

By the 1660s–1680s, Port Royal was the richest and bawdiest port in the Americas, notorious for excess. Contemporary writers likened it to a tropical Sodom. Pirates, privateers, merchants, enslaved people, and prostitutes jostled in its narrow streets amid taverns and gambling houses. Taverns were so prevalent that at the peak there was reportedly one tavern for every 10 to 20 residents—a sign of just how central drinking establishments were to daily life. In 1661 alone, 40 new tavern licenses were granted in Port Royal. Gold and silver coin flowed so plentifully from plunder that normal barter was often eschewed—hard currency was preferred for every transaction.

With nearly 6,500 inhabitants by the early 1690s packed into only 51 acres, Port Royal had become, as one scholar noted, a community “founded entirely on servicing the privateers’ needs.” Virtually everyone, from tavern keepers and artisans to officials, profited from the illicit trade and the spending sprees of seafaring raiders.

The social structure of Port Royal reflected this freebooting economy. While planters and merchants held formal status, it was the successful pirate captains and privateers who often flaunted the greatest wealth. Their crews caroused on shore alongside common sailors and smugglers. Contemporary observers marveled (and moralized) at the city’s “ungodly” atmosphere – one wrote even the “parrots of Port Royal” had learned to slur drunkenly, drinking from casks of wine alongside tavern patrons! This pirate haven earned its nickname—“the Wickedest City on Earth”—where the usual rules of society were drowned in greed and rum.

Inevitably, such excess courted disaster, not one created by man, but by the natural elements themselves. On June 7, 1692, Port Royal’s sinful reign was cut short by a cataclysmic earthquake (and ensuing tsunami) that shattered the town. In an instant, whole blocks of pirate taverns and brothels sank into the sea. Thousands perished in what many contemporaries saw as divine punishment for Port Royal’s iniquity. Though part of the town survived and rebuilding was attempted, Port Royal never fully regained its former glory. The English authorities, now less dependent on privateers, also began to clamp down on piracy. By 1687 anti-piracy laws were passed, and in the early 1700s Port Royal morphed from a sanctuary into an execution ground for pirates. Gallows Point at Port Royal saw the hanging of numerous pirate captains, such as Charles Vane and “Calico” Jack Rackham in 1720. Within a few decades, the golden age of piracy came to an end, and Port Royal settled into history – but the legends of its pirate inhabitants live on.