04/16/2026
As part of the St. Augustine History Festival, English corsair Sir Francis Drake and his raiders return to St. Augustine for an authentic re-creation of the 1586 sack of the city on Saturday, May 9, 2026.
Join Drake’s privateers, along with Spanish militia and townspeople, from 10:00 a.m. to 4:00 p.m. for a 16th-century-style military and civilian encampment at the Colonial Quarter Museum, located at 33 St. George Street in St. Augustine. Throughout the day, visitors can experience military drills, weapons demonstrations, and engaging living-history interpretations. Admission to the Colonial Quarter on Saturday is free and open to the public.
The historically accurate reenactment of the sacking and burning of the town will begin Saturday evening at 6:00 p.m. in the historic district, starting near the Governor’s House Museum. Drake’s men will come ashore as a clash erupts with Spanish soldados. As the fighting intensifies, Spanish troops and citizens retreat through the streets with Drake’s forces in pursuit. Skirmishes will continue north along St. George Street toward the field across from Ann O’Malley’s Deli and Pub on Orange Street, where the raid will again be interpreted for spectators to provide historical context.
The final engagement—featuring musket and cannon fire—will take place near the Santo Domingo Redoubt by the Visitor Center and parking garage. This dramatic conclusion symbolically represents the temporary withdrawal of Spanish colonial forces from the city. Following the destruction of the town, the Spanish ultimately returned to rebuild St. Augustine on the very streets we walk today.
This event is presented free of charge by the Historic Florida Militia and the Men of Menéndez, in partnership with the St. Johns County Cultural Council, the Colonial Quarter Museum, the University of Florida Historic St. Augustine, and Ann O’Malley’s Deli and Pub.
Additional information can be found at http://hfm.club
