Port Royal in the Buccaneering Era
Port Royal was an ideal pirate haunt because it provided a safe harbor with which to careen, repair and dock ships and stock up on supplies. Pirates used the port to sell their stolen goods, recruit more men and spend their treasure and partake in drunken festivities and other debauchery. These pirate haven ports were essential for the survival and widespread scale of privateering, buccaneering and piracy in the West Indies.
The central location of the settlement, combined with a deep harbor attracted pirates, merchants, tradesman, and prostitutes alike. As Port Royal grew, so did its reputation as a pirate haven. Port Royal was the fastest growing English settlement in the New World save for Boston. However, since England at the time was very weak and could not send troops to all of its territories, the Jamaican governor was forced to ask the pirates for protection in order to prevent the Spanish or French from controlling the city.
The buccaneers and privateers saw Port Royal as beneficial for themselves as well as it provided easy access to raid the Spanish merchant ships moving around the trade routes of the Spanish Main. In the West Indies there were only a few major water passages with which fleets could move through easily. The location of Jamaica also provided a good staging point for hundreds of attacks against Spanish settlements in Central America. From Port Royal many famous buccaneers sacked settlements all throughout the region.
From Port Royal Christopher Myngs sacked the city of Campeche and Henry Morgan conquered Panama Viejo, Maracaibo, Portobello and a few other Spanish settlements. Other famous buccaneers such as Roc Brasiliano, Edward Mansvelt, and John Davis operated out of Port Royal and staged their attacks on the Spanish Main from there.
The pirates were allowed free reign over the island because they provided essential defense services to help the British maintain control over the territory. During the 17th century the British did not have the capacity to garrison troops in all of its colonies and therefore the Jamaican governors turned towards the Brethren of the Coast to defend the city from the Spanish and in exchange they could do whatever they want. The same model had worked previously at Tortuga and allowed the French to gain a major foothold on Hispaniola with their colony of Saint-Domingue.
See Edward D'Oley
In 1657 only two years after the English captured Jamaica from the Spanish governor Edward D'Oley offered the same deal that the French did, protect the city and thus the colony and it can be used as a state sanctioned pirate haven. Within a few years the city boomed in terms of population and size. The city grew so rapidly after this that by 1659 there were over two hundred houses, shops and warehouses surrounding the main fort at Port Royal.
The idea was that by using the buccaneers Spain would be continually forced to defend its territories and therefore not having enough resources in order to retaliate against the other European powers who wanted to seize the islands of the West Indies.
See Thomas Modyford
In 1671, Henry Morgan and his fleet sailed from Port Royal in order to conquer and raid Panama Viejo. His fleet contained 37 separate ships that held 4 to 22 cannons on each. He also sailed with a small group of soldiers in order to provide a ground assault.