Piratical Life in St. Augustine: Then & Now

As the last stop for the Spanish treasure fleets before their return to Spain, St. Augustine attracted more than its share of pirates.

April 30, 2020

Like a pack of wolves, they simply waited for a Spanish ship full of gold and silver to experience difficulties and then they would pounce. When there were no flotillas filled with the treasures in sight, the pirates would simply raid the town looking for valuables.

The first big pirate attack occurred in June 1586 when the English pirate and corsair Sir Francis Drake was returning from his infamous raid on Cartagena. As his fleet of 23 ships and more than 2,000 raiders sailed up the Florida coast, they spied a light burning in the darkness. Upon investigating, they saw the light came from a Spanish watchtower marking the entrance to the St. Augustine harbor. Totally outgunned and outnumbered, the Spanish defenders and townsfolk fled into the swamps and marshes. Sir Francis Drake took anything of value and burned the town to the ground. Each year a reenactment of this tumultuous event is staged in the city in June.

In 1688, the notorious Jamaican pirate Robert Searles captured a Spanish ship and sailed it into St. Augustine’s harbor. He and his men stormed ashore, overpowered the guards and ran rampant through the town murdering and pillaging. Among the dead were several children, including a 5-year old girl killed by Searles. According to legend, the child’s ghost haunted him until he went mad and committed suicide years later. Searles’ raid is also reenacted in March each year.

Today, there are several pirate-related attractions, events and tours in town. The Pirate and Treasure Museum features the largest collection of authentic pirate and treasure artifacts in the world. Visitors to the museum relive the Golden Age of Piracy in a fantastic journey that immerses you in the harrowing life of a pirate and entertains with interactive fun. There’s even a treasure hunt for children that helps them explore the museum. Black Raven Adventures welcomes visitors aboard the Black Raven Pirate Ship, a replica of a 127 passenger Spanish Galleon. Enjoy an entertaining show featuring the best pirate actors in the state on this family friendly voyage. Drink with a Real Pirate while they regale you with adventurous tales on the Pirate Pub Crawl. On this 3 hour tour your Pirate tour guide will entertain and take you to pubs and taverns that the locals like to frequent.

kid with telescope and balloons
St. Augustine, Ponte Vedra & The Beaches