This is an excerpt from my book, Florida and the British before the American Revolution

In 1668, 1,500 residents called St Augustine home. Among them was an English prisoner, Henry Woodward who was one of founders of the South Carolina Colony. 

In 1666, Woodward was exploring the coast of the new colony working to pacify Native Americans. As part of his work he was granted by the Lords Proprietors possession of the new South Carolina colony. However, the next year Woodward was captured by the Spanish and taken to St Augustine as a prisoner. 

In St Augustine, the Spanish treated him well after he professed to be a Catholic. He was made an official surgeon in the town. In this role Woodward gained invaluable knowledge of the trading setup in Florida and how Spain had pacified Native Americans to make the colony prosperous. These lessons would be vital in the founding of Charles Town in 1670. 

In May 1668, Robert Searle, the noted pirate, sailed from Jamaica which had recently shifted from Spanish rule to British control, He captured a Spanish ship which had on board a prisoner Pedro Piquet who had been excommunicated from St Augustine after a dispute with the Governor. In this, the high age of English piracy Searle’s target was the royal chests which held silver in St Augustine and he was led there by Piquet. It was also at least on the surface retaliation for an attack by the Spanish on New Providence in the Bahamas. 

During the period from 1660 to 1725 English pirates regularly raided ships from Spanish and Portuguese Colonies in the Western Hemisphere and from the wealthy Ottoman and Mughal Empires in the Eastern hemisphere. England, which had just undergone a Civil War which had resulted in the execution of King Charles I and several years of Parliamentary rule that divided the country. In 1660, the monarchy was restored and England began on a course to enrich itself at others expense, a course which made it by 1900 the most powerful nation the world had seen since the Roman Empire. 

May 28, 1668 was the 82nd anniversary of Sir Frances Drake’s successful raid on St Augustine. That afternoon the 120 soldiers guarding St Augustine had been put on alert as an unfamiliar ship came into the Inlet. But in fact it was a delivery of flour from Veracruz, the annual provisions that the residents and soldiers of St Augustine so needed to survive. The next day those provisions would come ashore. 

However, that night a fisherman came ashore screaming, having been shot twice by Pirates. The soldiers heard the screams and within minutes a hundred pirates under Searle’s command were ashore. 

The pirates were before long everywhere in the town. People stormed out of their houses in panic but were easy targets for the English who used the narrow streets of St Augustine to their advantage. By morning, many of the residents had fled into the nearby woods. Nothing in the town was spared and the ship from Veracruz was also overwhelmed by the Pirates. Eventually the pirates left after ransoming off their prisoners for food and supplies. The pirates however refused to release Native Americans or freed African slaves and they took them back to Jamaica. 

Searle’s midnight May 28/29 raid left 60 residents of St Augustine dead with 75 prisoners. This finally convinced Spanish authorities to secure and fortify the town in the most expensive way possible – with the building of the Castillo de San Marcos. 

Searle’s raid resulted in the escape of Henry Woodward from captivity. The lessons Woodward took from his time in Florida led directly to the founding of Charles Town and the successful pacifying of some Native Americans in the Carolina’s. 

With the founding of Charles Town, Spain began to see its Florida Colony as an essential bulwark against rivals and a line of defense for its Caribbean colonies. St Augustine was a critical stop on Spain’s commercial shipping routes and had been proven once again vulnerable to English attacks. 

In 1686 a Spanish attempt to attack Charles Town was aborted. The next year the Spanish crown began actively encouraging slaves to run away from the English colonies to the north and to serve the crown in Florida. 

Absent the gold of other Spanish colonies in the Americas, Spain actively looked for those who would “serve” the crown in its military and economic needs in Florida. This included enticing slaves from English territories to flee to Florida and achieve freedom if they converted to Catholicism. 

This willingness to harbor runaway slaves would alter the relationship between Florida and its neighbors to the north for the next 90 years. In fact, African runaway slaves and Native Americans would prove exceedingly loyal to defending Spanish Florida from English invasions during the 1700’s.  

In addition, the massive Castillo de San Marcos was built at great expense to the crown to protect Florida from future English aggression. The Castillo itself took decades to complete, and was more fortified than anticipated because of pure luck – the use of Coquina rock to build the fort, quarried from nearby areas proved largely impenetrable.