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Port Royal is a town located at the end of the Palisadoes, at the mouth of Kingston Harbour, in southeastern Jamaica. Founded in 1494 by the Spanish, it was once the largest and most prosperous city in the Caribbean, functioning as the centre of shipping and commerce in the Caribbean Sea by the latter half of the 17th century. It was destroyed by an earthquake on 7 June 1692, which had an accompanying tsunami, leading to the establishment of Kingston, which is now the largest city in Jamaica. Severe hurricanes have regularly damaged the area. Another severe earthquake occurred in 1907. Port Royal became home port to English and Dutch government sponsored privateers who were encouraged to attack Spanish vessels, at a time when many European nations were reluctant to attack the powerful Spanish fleet directly. As a port city, it was notorious for its gaudy displays of wealth and loose morals, with the privateer crews spending their treasure in the many taverns, gambling houses and brothels which catered for the sailors. When the British and Dutch governments officially abandoned the practice of issuing letters of marque to privateers against the Spanish treasure fleets and possessions in South America in the later 16th century, many of the crews turned pirate to allow themselves to maintain their plundering illegally. Port Royal effectively became a pirate republic, and they continued to use the city as their main base during the 17th century. Pirates from around the world congregated at Port Royal, coming from waters as far away as Madagascar. The town became notorious in folklore as 'the wickedest city on Earth'. After the 1692 disaster, Port Royal's commercial role was steadily taken over by the rapidly growing nearby town (and later, city) of Kingston. Plans were developed in 1999 to redevelop the small fishing town as a heritage tourism destination to serve cruise ships. The plan was to capitalize on Port Royal's unique and fascinating heritage, with archaeological findings from pre colonial and privateering years as the basis of possible attractions.

The Taino historic indigenous people of the Caribbean occupied this area for centuries before European settlement. They used the area, which they called Caguay or Caguaya, during their fishing expeditions. Although it is not known whether they ever settled at the spot, they did inhabit other parts of Jamaica.

The Spanish first landed in Jamaica in 1494 under the leadership of Christopher Columbus, leading to the destruction of the Taino population. Permanent settlement occurred when Juan de Esquivel brought a group of settlers in 1509. They came in search of new lands and valuable resources, like gold and silver. Instead they began to cultivate and process the sugar cane. Much like the Taino before them, the Spanish did not appear to have much use for the Port Royal area. They did, however, retain its Taino name. By 1659 two hundred houses, shops and warehouses had been built around the fort; by 1692 five forts defended the port. "A report that the 300 men who accompanied Henry Morgan to Portobello in 1668 returned to the town with a prize to spend of at least £60 each (two or three times the usual annual plantation wage) leaves little doubt that they were right". Forced trade was rapidly making Port Royal one of the wealthiest communities in the English territories of North America, far surpassing any profit made from the production of sugar cane. Zahedieh wrote, "The Portobello raid [in 1668] alone produced plunder worth £75,000, more than seven times the annual value of the island’s sugar exports, which at Port Royal prices did not exceed £10,000 at this time." 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 from it.|author=|title=|source=

The taverns of Port Royal were known for their excessive consumption of alcohol such that records even exist of the wild animals of the area partaking in the debauchery. During a passing visit, famous Dutch explorer Jan van Riebeeck is said to have described the scenes:
The parrots of Port Royal gather to drink from the large stocks of ale with just as much alacrity as the drunks that frequent the taverns that serve it. There is even speculation in pirate folklore that the infamous Blackbeard (Edward Teach) met a howler monkey, while at leisure in a Port Royal alehouse, whom he named Jefferson and formed a strong bond with during the expedition to the island of New Providence. Recent genealogical research indicates that Blackbeard and his family moved to Jamaica where Edward Thatch Jr. is listed as being a mariner in the Royal Navy aboard HMS Windsor in 1706. Port Royal benefited from this lively, glamorous infamy and grew to be one of the two largest towns and the most economically important port in the English colonies. At the height of its popularity, the city had one drinking house for every 10 residents. In July 1661 alone, 40 new licenses were granted to taverns. During a 20 year period that ended in 1692, nearly 10,000 people lived in Port Royal. In addition to prostitutes and buccaneers, there were four goldsmiths, 44 tavern keepers, and a variety of artisans and merchants who lived in 2,000 buildings crammed into of real estate. 213 ships visited the seaport in 1688. The city's wealth was so great that coins were preferred for payment over the more common system of bartering goods for services. Following Henry Morgan's appointment as lieutenant governor, Port Royal began to change. Pirates were no longer needed to defend the city. The selling of slaves took on greater importance. Upstanding citizens disliked the reputation the city had acquired. In 1687, Jamaica passed anti piracy laws. Consequently, instead of being a safe haven for pirates, Port Royal became noted as their place of execution. Gallows Point welcomed many to their death, including Charles Vane and Calico Jack, who were hanged in 1720. About five months later, the famous woman pirate Mary Read died in the Jamaican prison in Port Royal. Two years later, 41 pirates met their death in one month.

Under British rule the Royal Navy made use of a careening wharf at Port Royal and rented a building on the foreshore to serve as a storehouse. From 1675, a resident Naval Officer was appointed to oversee these facilities; however, development was cut short by the 1692 earthquake. After the earthquake, an attempt was made to establish a naval base at Port Antonio instead, but the climate there proved disagreeable. From 1735, Port Royal once more became the focus of the Admiralty's attention. New wharves and storehouses were built at this time, as well as housing for the officers of the Yard. Over the next thirty years, more facilities were added: cooperages, workshops, sawpits, and accommodation (including a canteen) for the crews of ships being careened there. A Royal Naval Hospital was also established on land a little to the west of the Naval Yard; and by the end of the 18th century a small Victualling Yard had been added to the east (prior to this ships had had to go to Kingston and other settlements to take on supplies). Many of the Dockyard buildings (most of which were of timber construction) were subsequently demolished or destroyed (some in the 1907 Kingston earthquake, others by Hurricane Charlie in 1951). A few remain in place, however, including the Naval Hospital complex, some of the steam engineering buildings and a set of officers' houses. There is also a slipway, completed as late as 1904, which (with its accompanying sheds) was designed for housing and launching torpedo boats, stationed there for the Yard's protection. In 2014, it was announced that some of the Historic Naval Hospital buildings would be restored to house a museum as part of a broader Port Royal Heritage Tourism Project.

The town grew rapidly, reaching a population of around 6,500 people and approximately 2,000 dwellings, by 1692. As land on which to build diminished, it became common practice to either fill in areas of water and build new infrastructure on top of it, or simply build buildings taller. Buildings gradually became heavier as the residents adopted the brick style homes of their native England. Some urged the population to adopt the low, wooden building style of the previous Spanish inhabitants, but many refused. In the end, all of these separate factors contributed to the impending disaster. On 7 June 1692, a devastating earthquake hit the city causing most of its northern section to be lost – and with it many of the town's houses and other buildings. Many of the forts were destroyed, as well; Fort Charles survived, but Forts James and Carlisle sank into the sea, Fort Rupert became a large region of water, and great damage was done to an area known as Morgan's Line. The earthquake and tsunami killed between 1,000 and 3,000 people combined, nearly half the city's population. Disease ran rampant in the next several months, killing an estimated 2,000 additional people. The historical Jamaica earthquake of 7 June 1692 can be dated closely not only by date, but by time of day as well. This is documented by recovery from the sea floor in the 1960s of a pocket watch stopped at 11:43 a. m., recording the time of the devastating earthquake. The earthquake caused the sand under Port Royal to liquefy and flow out into Kingston Harbour. The water table was generally only two feet down before the impact, and the town was built on a layer of some 65 feet (20 m) of water saturated sand. This type of area did not provide a solid foundation on which to build an entire town. Unlike the Spanish before them, the English had decided to settle and develop the small area of land, even while acknowledging that the area was nothing but "hot loose sand". According to Mulcahy, "[Modern] scientists and underwater archaeologists now believe that the earthquake was a powerful one and that much of the damage at Port Royal resulted from a process known as liquefaction." Today, the area is a shadow of its former self with a population of fewer than 2,000 that has little to no commercial or political importance. The area is frequented by tourists, but is in a state of disrepair. The Jamaican government has recently resolved to further develop the area for its historic and tourist value. This is in part a result of abandonment of plans begun in the early 1960s to develop the town as a cruise ship port and destination. The plans stimulated the archaeological explorations on the site which, in turn, led to the suspension of development solely as a port but now included archaeological and other attractions. In 1981, the Nautical Archaeology Program at Texas A&M University began a 10 year underwater archaeological investigation of the portion of Port Royal that sank underwater during the 17th century. The program focused on an area that had sunk directly into the sea and suffered very little damage. Due to very low oxygen levels, a large amount of organic material could be recovered. The efforts made by the program have allowed everyday life in the English colonial port city to be reconstructed in great detail. In 1998, the Port Royal Development Company commissioned architectural firm The Jerde Partnership to create a master plan for the redevelopment of Port Royal, which was completed in 2000. The Royal Naval Dockyard also includes the headquarters for the Admiral of the Royal Navy. The redevelopment plan also includes a five star hotel. Today, Port Royal is known to post medieval archaeologists as the "City that Sank". Robert Marx considers it the most important underwater archaeological site in the western hemisphere, yielding 16th–and 17th century artifacts and many important treasures from indigenous peoples predating its 1518 founding, some from as far away as Guatemala. Several 17th and early 18th century pirate ships sank within Kingston Harbour and are being carefully harvested, under controlled conditions, by various teams of archaeologists. Other "digs" are staked out along various quarters and streets by different teams. By 2019, a floating pier where a cruise ship could dock had been built; the first ship arrived on 20 January 2020. Tourists from a few ships (after the effects of the COVID 19 pandemic have ended) might be beneficial to the town, but "there's still much work to be done if the town will become the 'world class heritage, environmental and cultural attraction according to a BBC Travel report published in September 2020. Another report that month discussed the well funded Living Heritage Programme, which was seeking "to transform the town into a SMART, safe and secure community with a vibrant local economy, preserved cultural heritage and protected natural environment".