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.

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.

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.

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