In 1586 Francis Drake with a large flotilla, sacked St. Augustine. Drake entered the city virtually uncontested and left it in ruins.

In 1666 the highly successful French pirate, Nicholas Grammot, tried his luck. He too was turned away in a skirmish just south of Matanzas Inlet.

In March 1683 a band of three hundred marauders landed near Matanzas Inlet, but were discouraged after being caught in an ambush on Anastasia Island.

1688 Robert Searle's attack failed when his crew chose to sack the town instead of attacking the fort. The captain was lucky to escape with his life.

In 1740, When the Spanish government neglected to send the annual subsidy for the previous two years, Governor Montiano informed the Spanish regional government in Cuba about his intention to arm a ship as a privateer to supply the city with food. "Privateers" were independent pirates sanctioned by their governments with the requirement to share their booty with the government and merchant sponsors.

In October, St. Augustine’s privateers sailing aboard the Campeche, captured a ship filled with rice off Charleston, South Carolina. At times as many as thirteen English vessels were anchored under the Castillo's guns, all Privateering prizes. By the end of the year, more than forty English ships had been captured and their cargoes sustained the Spanish population.

One St. Augustine privateer (pirate to the English) was Francisco Menendez. Menendez was an escaped Mandingo slave from the British Colonies. He converted to Catholicism and was granted his freedom by the Spanish governor. In 1738 Governor Montiano established Fort Mose, the first free black settlement in North America. Just to the north of St. Augustine, the fort served as a buffer from anticipated British attacks from the North. This Fort and village was operated by Captain Menendez for over 20 years. In 1740 he took a commission as a privateer. He was captured by the British ship Revenge in July 1741. He was tied to a gun and the British ordered the ship's doctor to pretend to castrate him. Later he was given 200 lashes by the British and pickled (given a vinegar and salt bath). They attempted to sell him back into slavery but by 1752 he was again in command at Fort Mose.

In 1756 the Seven Years War between England and France began.  The French soon found St. Augustine’s Matanzas Bay to be a perfect port for refitting their ships for voyages along the coast. By 1758, the French were arriving on a weekly basis with a newly captured English ship. In the fall of that year the French pirates arrived shepherding in eleven English vessels.
 

When Spain joined with France in the war against England in January of 1762 the English captured Havana. Now surrounded by the English occupying Havana and her colonies to the north, once again, St. Augustine turned to Privateering to battle starvation. In only ten days, the San Christoval captured three English ships filled with essential food.  Two of her prizes sank while trying to cross the bar at the inlet and never made it into Matanzas Bay. Three more privateers joined the San Christoval on subsequent voyages. Together they were able to feed the residents with captured English supplies. 

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