Every year the rich and colorful history of Florida's oldest city is celebrated with two historical pirate battle-enactments and an elaborate pirate festival. In early March a group called Searles Buccaneers (searlesbucs.com) re-enact Captain Robert Searles sacking of the town in 1668. The Searles Buccaneers return in June alongside the St. Augustine Men of Menendez -- both members of the Historic Florida Militia (historicfloridamilitia.org) -- to re-stage the raid and subsequent burning of the town by Sir Francis Drake in 1586. Finally, the golden age of piracy is celebrated in early November with a weekend of rollicking frivolity called the St. Augustine Pirate Gathering.
Wearing period costumes and using authentic antique weapons, the Searles Buccaneers stage a historically accurate recreation of the sacking of St. Augustine in a two-day weekend event in early March. Beginning on a Friday, a military-style encampment complete with drills and demonstrations sets the mood at the Fountain of Youth Park (fountainofyouthflorida.com). The main event, the battle and sacking re-enactment, begins the next afternoon at around 5 p.m. in the old city where the invading pirates take the townspeople by surprise and battle Spanish garrison guards from the plaza to the Old City Gate. Each year, the Buccaneers welcome newcomers wishing to join the campaign in the roles of townspeople, garrison guards, native Americans or buccaneers, providing appearance guidelines are met.
Every June for more than two decades the Searles Buccaneers are joined by the St. Augustine Men of Menendez to recreate the infamous invasion of St. Augustine by Sir Francis Drake. Similar to the March re-enactment, Drake's invasion begins with a period military camp-out. Just before sundown on Saturday, the night is filled with cannon fire and the clanking of swords as the two factions stage a one-sided fight from the City Gates on St. George Street to the Plaza de la Constitucion.
Finally, in early November, all things from the golden age of piracy are celebrated during the St. Augustine Pirate Gathering. This rollicking event, held at St. Frances Field and Historical Quarter in downtown St. Augustine, features such diversities as a pirate pub crawl, privateer parade, pirate land battle and pirate mutiny featuring re-enactors from a historical preservation group. As the air rings with the sound of pipes and sea shanties, a weekend of jollification for all is rounded out with weapons demonstrations, a sailor’s encampment and a thieve's market.
