In December 1654, Oliver Cromwell, Lord Protector of England, sent an invasion force under the commands of Admiral Penn and General Venables to capture Hispaniola. The force landed on Hispaniola with plans for an overland attack to the city of Santo Domingo. However, the ships landed 50 kilometers from the city, without enough food and water. Polluted water caused sickness among the men, and the group became mutinous before reaching the Spanish forces.
Many men ran, a few fought, and only a landing party of sailors covering their retreat to the ships saved the rout from being a massacre. At the end of the battle, a third of the group was dead or missing. However, the British crew feared Cromwell's response to their failure at Santo Domingo, and they decided to attack another Spanish holding, this time one with much weaker defenses: Jamaica.
Approximately 8,000 men on 38 ships arrived in Kingston Harbor on May 10, 1654,. The British leaders gave strict orders to avoid the cowardice that they'd seen in Santo Domingo, but this force only met 1,500 Spanish settlers, only about a third of whom could bear arms.
Within weeks the construction of a Fort, known as Fort Cromwell or Passage Fort, began at the tip of the Palisadoes peninsula, a perfect place to control access and defend the harbor. A small community of merchants, mariners, craftsmen and prostitutes built up around the fort and the area became known as Point Cagway but later renamed to Port Royal. The Fort was also later renamed to Fort Charles.
Although Port Royal was designed to serve as a defensive fortification, guarding the entrance to the harbor, it assumed much greater importance. As a result of its location within a well-protected harbor, its flat topography, and deep water close to shore, large ships could easily be serviced, loaded, and unloaded. Ships' captains, merchants, and craftsmen established themselves in Port Royal to take advantage of of the trading and outfitting opportunities. As Jamaica's economy grew and changed between 1655 and 1692, Port Royal grew faster than any town founded by the English in the New World, and it became the most economically important English port in the Americas.Coinciding with the city's early development between 1660 and 1671, officially sanctioned privateering was a common practice, and nearly half of the 4000 inhabitants were involved in this trade in 1689. The buccaneer era greatly enriched the port, but it was a short-lived and colorful period that England was supposed to end by the conditions of the 1670 Treaty of Madrid. Privateering and/or piracy, however, continued in one form or another into the 18th century. Indeed, it was the Spanish money flowing into the coffers of Port Royal, through trade and plunder, that made the port so economically visible.
After 1670, the importance of Port Royal and Jamaica to England was increasingly due to trade in slaves, sugar, and raw materials. It became the mercantile center of the Caribbean, with vast amounts of goods flowing in and out of its harbor as part of an expansive trade network, which included trading and/or looting of coastal Spanish towns throughout Spanish America. It was a wealthy city of merchants, artisans, ships' captains, slaves, and, of course, notorious pirates, who gave it its 'wickedest city in the world' reputation.
Only Boston, Massachusetts, rivaled Port Royal in size and importance. In 1690, Boston had a population of approximately 6000, while population estimates for Port Royal in 1692 range from 6500 to 10,000. Many of the city's 2000 buildings, densely packed into 51 acres, were made of brick (a sign of wealth), and some were four stories tall. In 1688, 213 ships visited Port Royal, while 226 ships made port in all of New England. In addition, the probate inventories of many of Port Royal inhabitants reveal much prosperity and the observation that, unlike the other English colonies, Jamaica used coins for currency instead of commodity exchange.
In short, Port Royal was the most successful entrepot in the
17th-century English New World. Its social milieu was quite
different than either that of New England, with its religiously ordered
towns, or of the tobacco-driven economy of Maryland and Virginia.
Port Royal had a
tolerant, laissez-faire attitude that allowed for a diversity of
religious expression and lifestyles. There is early mention of
merchants, who were Quakers, 'Papists,' Puritans, Presbyterians, Jews,
or, of course, Anglicans, practicing their religion openly alongside
the free-willing sailors and pirates who frequented the port.
Source: Texas A&M Nautical Archaeology