The island of Jamaica was settled in 1509 by Juan de Esquivel. The Spanish held it for more than a century until 1655 when an English squadron landed in what is now Kingston. The small army sacked and burned the Spanish settlements, conquering the island. Spain has never retaken the island.

The soldiers set up the city of Port-Royal and the colony began the cultivation of sugarcane. This income is soon augmented by a growing level of Privateering based in Port-Royal.

Port Royal was conveniently situated on the trade routes to and from the Spanish Main and Spain. The port provided a safe harbor for pirates while providing them easy access to merchant prey and for launching raids on Spanish settlements. The harbor was large enough to accommodate their ships for careening and repair. Henry Morgan attacked Panama, Portobello, and Maracaibo from Port Royal. The pirates Roche Brasiliano, Edward Mansfield and John Davis, at times, made Port Royal their home port.

The English lacked sufficient troops to defend Port Royal and Jamaica from the Spanish and French so the Jamaican government turned to the pirates to defend the city.

Port Royal grew to be one of the two largest towns and the most economically important port in the English colonies but by the 1660s, the city had gained a reputation as the 'wickedest town on Earth where most residents were pirates, cutthroats, or prostitutes. Port-Royal had become the greatest pirate haven in the Caribbean and her governor, Thomas Modyford issued Letters of Marque and Reprisal to any man with a boat who made an oath not to attack English ships..

Port Royal began to change. Pirates no longer needed to defend the city. The slave trade grew in economic importance took. In 1687, the colony had grown in importance. As plantations grew so did a higher class of citizens. Jamaica passed anti-piracy laws. The once pirate haven of Port Royal became their place of execution. Notable pirates found their end on Gallows Point included Charles Vane and Calico Jack were hanged in 1720. Two years later, forty-one pirates met their death in one month.

On June 7, 1692, a large part of Port-Royal was destroyed by a devastating earthquake which sunk most of the town into the sea. Thousands are killed and Port-Royal was never fully rebuilt. The British throne did very little to help in rebuilding. The city was slowly rebuilt and became more respectable.

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