Pirate Attack : Drake and Searles Raid St. Augustine

It’s Talk Like a Pirate Day! To commemorate this fun holiday, Governor’s House is retelling the tales of Sir Francis Drake and Robert Searles, two feared men who raided our town either to intimidate or gain material wealth.

Sir Francis Drake was a favorite of Queen Elizabeth I and a sworn enemy of Spain.  The Spanish dubbed him “El Draque,” or “The Dragon.”  Queen Elizabeth sanctioned Drake’s actions, thus making him a privateer sailing under a “letter of marque” and escalating the tension between Protestant England and Catholic Spain.  Drake raided Spanish settlements in and around the Caribbean such as Santiago, Santo Domingo, and Cartagena.  In 1586 he raided St. Augustine, a feat depicted in a map drawn by Baptista Boazio, which historians laud as the first map of St. Augustine.  The Boazio map shows Drake’s twenty-three ships poised to attack and burn the city.

An old painted map showing Anastasia Island and St. Augustine under attack from Sir Francis Drake's fleet. A giant blue fish in the Atlantic Ocean can be seen in the lower left corner of the map. A wooden fort stands where present-day Castillo de San Marcos is.

Drake sailed to St. Augustine with two thousand men.  Captain Christopher Carlile took one thousand of these men to Anastasia Island across from the Spanish wooden fort that was in the city at the time of the attack.  The onslaught was such that Spanish soldados abandoned the fort. One of the earliest known maps of St. Augustine, Boazio’s 1586 map, depicts Drake’s raid and is held at the Library of Congress as part of the Jay Kislak Collection.

In modern times, the Historic Florida Militia, Inc. reenact Drake’s Raid each year as a living history event.  Two years after the actual raid, Drake himself took part, as second-in-command of the English fleet, in the battle against the Spanish Armada.  Ten years after his raid on St. Augustine, he was dead of dysentery.

Englishman Robert Searle visited St. Augustine approximately eighty years after Drake.  Also a privateer, he sailed from Jamaica in search of silver ingots (blocks of silver) that were cached in the royal treasurer’s stores.  Searle and his crew sailed into St. Augustine on a Spanish vessel they had captured in Havana.  One of the men aboard ship was former St. Augustine resident Pedro Piques who had been run out of town by the governor and who had no squabbles helping the pirate crew navigate the inlet.

A black and white photograph of Castillo De San Marcos seen from west. A moat filled with water surrounds the Castillo. Mantanzas Bay and the Atlantic Ocean can be seen in the background.

Upon arrival in St. Augustine, Searle and his crew raided homes, government buildings, and the church.  They kidnapped dozens, spiriting away non-white residents into slavery and vowing to return one day to take St. Augustine.  Searle’s most lasting effect on the city lay in the Crown’s response to his attack.  In Spain, Queen Regent Mariana was finally convinced that St. Augustine merited an enforced fortification.  She gave permission to build a coquina structure, and in 1672 builders laid the first stone of the Castillo de San Marcos that we know today.

Searle, whose alias was John Davis, had meanwhile sailed with famed Sir Henry Morgan around Central America.  He met his death allegedly in a duel in Honduras.

The Historic Florida Militia also reenacts Searle’s Sack each year in May when the attack took place.

9 thoughts on “Pirate Attack : Drake and Searles Raid St. Augustine

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  4. Scott Conner

    What was the ultimate outcome of both pirate raids? Was the city burned? Did the pirate raids just withdraw after doing their crimes and damage or how did they leave the city?

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    1. Hi Scott,

      After both raids, there was very little left of the St. Augustine presidio. Both Searle and Drake left the city on their ships after their raids; Drake continued sailing north to Roanoke Colony in North Carolina, and Searle rescued an Englishman named Henry Woodward before returning to his home of Jamaica.

      Pedro Menendez wrote to the Spanish Crown and persuaded them to focus all of their attentions on St. Augustine and its fortification, so at this time the Spanish settlements on Parris Island and Santa Elena, both in South Carolina were abandoned. Both raids provided further reason and determination for the Spanish to make a more structurally sound and protected fort, which began the construction of the coquina built Castillo de San Marcos as we know it today.

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