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While in the vicinity of Cuba in 1668, English pirate Robert Searles captured a Spanish supply ship and a brigantine on its way to Florida. On board was French surgeon Pedro Piques who had worked at the fort in St. Augustine. When he told Searles about the vulnerable city, Searles decided to sail there.

Searles maneuvered one of his captured ships into view of the fort and ordered the imprisoned crew to appear on deck and perform their usual tasks. The "supply ship" disguise fooled the presidio launch. The townspeople thought the supply ship would wait for favorable wind and dock in the morning.

Around midnight, Searles quietly maneuvered his ship into harbor. He and his pirates landed and quickly spread out, killing or capturing anyone they found while pillaging homes and shops. The townspeople, including the governor and the soldiers, fled into the woods.

Pirate of the Month

He was captured by the Spaniards in Italy and forced to serve them while chained to their galley.

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Did you know?

  • At the height of its popularity, Port Royal, Jamaica had one drinking house for every ten residents. In July 1661 alone, 41 new licenses were granted to taverns.

  • Pirates wore an earring to ensure they died with at least one piece of treasure to buy their way into 'Fiddler's Green' (sailor's paradise in heaven).

  • The reason you've heard of most well known pirates is that they were captured and killed, or brought to trial where their exploits were recorded. But pirate captain Henry Every was made famous because he evaded capture after his piratical exploits.

  • Many pirates had eye patches, peg legs, or hooks. Ships in the 17th and 18th century were extremely dangerous places to work, so pirates would commonly lose limbs or even eyes during battle. 

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