Port Royale was the English capital city of Jamaica. Known as the “wickedest city on Earth,” the port town was a pirate haven which served as a base of operations for privateers and pirates who sought to plunder Spanish ships and settlements. It was located on the sands at the mouth of Kingston Harbour, one of the largest natural harbors in the world.

Originally founded by Spanish settlers in 1518, the town saw little growth. Jamaica was not a particularly important island to the Spanish, and the sandy terrain at the harbor offered neither fertile ground nor stable foundations. The colony served only as a strategic outpost, until an English invasion fleet arrived and captured the island in 1655.

Within several years of the English takeover, hundreds of houses filled the town, and soon five forts were constructed to defend against any Spanish counterattack. Jamaica became a constant thorn in Spain’s side. Under the rule of Governor Thomas Modyford, privateers were hired from across the Caribbean to defend the island from Spanish aggression, and to raid Spanish targets in the area. During this era, Port Royal was the home port of the famous Captain Henry Morgan, who grew wealthy by sacking cities in every direction.

The port was in a prime position, offering safe refuge for pirates in the middle of the Spanish Main. They could utilize the westward-blowing crosswinds to head south to attack anything along the coasts of South America and Panama, and quickly return before the Spaniards could prepare a response. Similarly, the Yucatan Peninsula of Mexico was not far away, and pirates could reach the cities there with great speed. The island’s proximity to Cuba also allowed for easy attacks on that island as well. Adding to the benefits of its location, the French pirate haven of Tortuga, off the northern coast of Hispaniola, was also in easy reach. This allowed pirates from either nation to collaborate and recruit one another, facilitating devastating raids.

Port Royal became one of the busiest ports in the region, accumulating thousands of residents. At its peak, a new ship arrived every other day – in 1688 alone, 213 vessels called at the port. The city’s reputation sunk further the more active it became. Prostitution was common, as the town was set up solely to cater to the cutthroats that called it their base. One count of the local drinking establishments found one tavern for every ten residents. Stories circulated that even the local parrots could be found drunk, as the wildlife feasted on the excess alcohol.

The port’s entire economy was powered by plunder. Henry Morgan’s raid on Porto Bello alone brought in seven times more wealth than the annual value of the entire island’s sugar exports. Local merchants sponsored so many raids against Spanish trade vessels that they became desperate for goods, causing Spanish smugglers to break their country’s mercantilist laws and trade with the English merchants, further enriching Port Royal. Spain was so busy defending their holdings from privateers that it was unable to spare enough forces to retake the island.

Later, Port Royal began to shed its status as a pirate haven. Declining Spanish power meant that piracy was no longer a necessity for defense. Residents were unhappy with the reputation of their city, and in 1687, anti-piracy laws were passed. The Royal Navy increased its presence and began using the port as a base. Soon, Port Royal was transformed into a place where pirates went to die rather than drink. Numerous pirates were tried and hanged, with their bodies gibbeted over the harbor as a warning to others.

In 1692, a massive earthquake struck Jamaica. Port Royal was ill-suited to withstand the tremors. Most of the city had been built on the sandy shores, which shifted and liquefied during the quake. The city’s rapid expansion drove residents to simply fill in the water with more sand to make space, or just make buildings taller. Port Royal was utterly destroyed in the earthquake. People speculated that it may have been retribution from God for the city’s evil ways. Some attempts were made to rebuild, but they were eventually abandoned and the port ceased to exist.

Port Royal was featured in the Pirates of the Caribbean film series, serving as the English port which the main characters were from. Unlike reality, this version of Port Royal was a small fortress town built between cliffs. Similarly, the harsh treatment of pirates by city officials seen in the films was only the norm towards the end of the town’s era. Port Royal also played a significant role in the eponymous video game series Port Royale, in which the player must visit the port to begin the main story quest.