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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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Francis Drake was the most successful privateer in maritime history.

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Did you know?

  • Pirates thought that having women on board their ship was bad luck.  It's why pirate femmes like Mary Read initially lived a life of piracy as men!

  • Most pirates stole their ships because they couldn't afford them.  Once they'd capture a ship, they'd convert it for pirate life by making more room for sailor living quarters and strengthening the decks to hold heavy cannons.

  • The difference between a pirate and a privateer is that privateers are sanctioned by respective governments and they don't attack ships from their own country. Pirates harass anyone passing by.

  • A galleon ship was armed to the teeth. It typically carried 74 guns, 36 of which were mounted on either side of the ship. The two guns were mounted aft.

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