2017:  Saturday March 4th

2018: Saturday March 3rd (20th Anniversary of Re-enactment!)

2019: Saturday March 2nd

EVENT INFORMATION: Join us on the first Saturday in March in the reenactment of the “1668 Sack of St. Augustine” in St. Augustine Florida, our nations’ oldest city.  During the day a 17 century-style military encampment will be open to the public at the Fountain of Youth Park (Free with paid admission) and will play host to drills, demonstrations and living history interpretation  from 10:00 AM to 4:00 PM. The reenactment of the sacking and burning of the town will commence Saturday evening at 4:30 PM in the old city, beginning at the Plaza and ending at the Old City Gates. We are always looking for new recruits to portray townspeople, garrison soldiers, Native Americans, and buccaneers! Our focus is on an accurate historical impression, using correct materials, styles, and equipment. You need not be a historian, actor, or military enthusiast to participate however if you are interested please be sure to read the Rules & Information. The “Sack of St. Augustine: Capt. Robert Searle’s Raid of 1668” is a historical reenactment sponsored by Searle’s Buccaneers and the Men of Menendez (members of the Florida Historic Militia), with the assistance of the St. John’s County Tourist Development Council. 


Pikemen form up before drill. Many of our newer members take part in the pike block, as muskets can get expensive!

Searles Musketeers firing at the sea wall in St. Augustine. The direct result of the attack, the Castillo San Marcos , is in the background.

Searles Musketeers firing at the sea wall in St. Augustine. The direct result of the attack, the Castillo San Marcos , is in the background.


St. Augustine, Florida, that “noble and loyal city” is the oldest inhabited European settlement in North America.  Founded by Don Pedro Menendez de Aviles in 1565, it was a valuable outpost of the Spanish Empire, serving as a haven for the imperial treasure fleets sailing from the New World to Spain.  For over a century and a half, beginning with Sir Francis Drake’s raid in 1586 and ending with General James Oglethorpe’s attack in 1743, English troops and buccaneers repeatedly tried to wrest this strategic port from the Spaniards.

In 1655, Oliver Cromwell’s “Western Design” resulted in the capture of Spanish Jamaica, thus providing English freebooters with a safe base from which to plunder the Spanish Main.  The “Golden Age of Piracy” had begun!

In 1668, Captain Robert Searle and his privateers sailed from Jamaica to loot the silver ingots held in the royal coffers at St. Augustine.  Under the cover of night, they slipped into the harbor and attacked the sleeping town, killing sixty people and pillaging government buildings, churches and homes.  The devastation wrought by these bloodthirsty pirates prompted Spain’s Council of the Indies to issue money to build a massive stone fortress on Matanzas Bay to protect the city.  The Castillo de San Marcos still stands as an enduring reminder of Florida’s exciting heritage!

Searle’s Sack of St. Augustine is made possible in part by a grant from the St. Johns County Tourism and Development Council.

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