Join Historic Florida Militia on the first weekend in March for the reenactment of Searle’s Sack of St. Augustine, one of only two true pirate attacks to have occurred in the nation’s oldest city.

The Historic Florida Militia’s portrayal of Searle’s Sack recreates the famous bloody pirate raid on St. Augustine in 1668 led by English Privateer Captain Robert Searle when he and his crew laid siege to the city and its inhabitants. Searle and his privateers sailed from Jamaica to loot the silver ingots held in the city’s royal coffers under the cover of night, slipping into the harbor and attacking the sleeping town, killing sixty and pillaging government buildings, churches, and homes. The devastation wrought by these pirates prompted Spain’s Council of the Indies to issue money for a massive stone fortress on Matanzas Bay to protect the city known as the Castillo de San Marcos. 

This year marks the 355th Anniversary and re-enactors from all over the country will participate in this twenty-fifth annual event.

This living history event, presented by Searle’s Buccaneers, Historic Florida Militia, and the St Augustine Historical Society, with the assistance of the St. John’s County Tourist Development Council, has three distinct parts.

1. A saunter will announce the arrival of the raiding pirates and begin near the Cathedral Basilica at 4:30 PM on Friday, March 3rd. Historically clad re-enactors will proceed north on St. George Street to the Santo Domingo Redoubt on Orange Street.
2. The Searle’s Sack encampment will take place on Saturday, March 4th from 10 AM to 4 PM at the Oldest House Museum Complex located at 14 St. Francis Street.  Visitors can see colonial St. Augustine with period demonstrations of weapons, clothing, and equipment, as well as reenactments of camp life and social activities.
3. The reenactment of the battle between the privateers and the city’s Spanish defenders will take place at 4:30 PM on Saturday, March 4th, beginning at the Plaza de la Constitución and ending near the Old City Gate. The English privateers will head north on St. George Street from the Plaza and the battle will commence when they clash with the Spanish defenders, stationed at the Santo Domingo Redoubt on Orange Street.  (across from Potter’s Wax Museum.) See period re-enactors demonstrate how Spanish settlers fought off Searle and his pirates. Beating drums, waving flags, sword fights, musket and cannon firings, and pike pushes are all part of the dramatic recreation of this famous attack on our town.