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Robert Searles

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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.

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Did you know?

  • Pirates had workman's comp! Each captain took care of the injured by compensating crewmen for being maimed or losing a limb. And each captain had his own "rates:" loss of right arm, 600 pieces; left arm, 500 pieces; right leg, 500, etc.

  • The Castillo de San Marcos was built immediately after Captain Robert Searles sacked St. Augustine, Florida in 1668. Sir Francis Drake razed the city 82 years earlier.

  • "Walking the Plank" is a Hollywood myth.  Pirates were more likely to throw men overboard, hang them from the yardarms, or keelhaul them.  

  • Every Pirate Captain established a set of rules called the "Articles." Every member of the crew signed articles of piracy over a boarding axe prior to setting sail - symbolic to the oath the pirate just promised his fellow sailors.

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