Sir Francis Drake’s Raid on St. Augustine: A Devastating Blow to Spanish Florida

By Joe Marzo

In June 1586, the bustling Spanish settlement of St. Augustine—the oldest permanent European city in what would become the United States—faced one of its greatest threats. Sir Francis Drake, an English sea captain and privateer, led a daring attack that devastated the city, setting fire to buildings and fortifications and dealing a major blow to Spain’s stronghold in Florida. Drake’s raid was a key moment in the broader struggle between European powers for dominance in the New World, and it underscored the vulnerability of Spain’s North American empire.

Drake’s raid was part of a larger, ongoing conflict between Spain and England that spanned much of the 16th century. The two nations were bitter rivals, driven by religious and political differences as well as economic competition for control of the riches of the Americas. Spain, a Catholic empire, had built a vast overseas empire that included much of Central and South America, as well as Florida. Meanwhile, England, a Protestant nation, sought to challenge Spain’s dominance on the high seas and gain its own share of the wealth flowing from the New World.

By the 1580s, Sir Francis Drake had already earned a fearsome reputation as a privateer—essentially a state-sanctioned pirate—working for the English Crown. He had raided Spanish ships and settlements throughout the Caribbean and had even circumnavigated the globe, gaining fame and fortune along the way. In 1585, Queen Elizabeth I ordered Drake to lead a large-scale expedition to the West Indies and the Spanish Main, with the mission of disrupting Spain’s trade routes, plundering its colonies, and generally causing as much damage as possible to Spain’s empire.

Drake’s fleet, consisting of 23 ships and over 2,000 men, sailed from England in September 1585. His campaign of destruction began in the Caribbean, where he sacked the Spanish towns of Santo Domingo (in present-day Dominican Republic) and Cartagena (in present-day Colombia). Both raids were highly successful, yielding treasure and supplies, and Drake’s forces left behind a trail of burning cities and frightened Spanish colonists.

After leaving Cartagena, Drake turned his attention to Florida. Spain had established St. Augustine in 1565 as a military outpost to protect its shipping lanes and territorial claims.

The settlement was a key part of Spain’s defense network in the Americas, guarding the northern edge of its empire and providing a base for Spanish ships as they traveled along the Gulf Stream toward Europe. Drake’s decision to attack St. Augustine was strategic—by striking at Spain’s northernmost stronghold, he could weaken its ability to protect its colonies and harass its ships.

In late May 1586, Drake’s fleet arrived off the coast of Florida. The English ships anchored near the mouth of the St. Johns River, and Drake sent scouting parties to assess the defenses of St. Augustine, which lay just to the south. At the time, St. Augustine was a modest settlement, home to a small garrison of Spanish soldiers and a few hundred civilians. Its fortifications consisted of wooden palisades and earthworks, which were no match for Drake’s heavily armed fleet.

On June 6, 1586, Drake launched his attack. The English forces landed near St. Augustine and quickly overpowered the Spanish defenders, who were caught off guard by the sudden assault. The Spanish governor of Florida, Pedro Menéndez Márquez, and his troops fled the settlement, retreating into the surrounding woods to avoid capture. The remaining residents of St. Augustine, including women and children, also fled in panic, leaving the town virtually undefended.

Drake’s men quickly took control of the settlement and began looting its buildings. They ransacked the Spanish garrison, stole supplies, and destroyed everything of value they could find. According to historical accounts, Drake’s forces even captured several large cannons, which they spiked (rendering them unusable) before taking them aboard their ships as trophies.

After plundering the settlement, Drake ordered his men to set fire to St. Augustine. The flames spread rapidly, engulfing the wooden structures and reducing much of the town to ashes. The Spanish church, government buildings, homes, and military outposts were all destroyed. In a matter of hours, St. Augustine, the jewel of Spain’s Florida colony, was left in ruins.

The scale of the destruction was immense, and for the Spanish colonists, the raid was a catastrophe. With their homes destroyed and their military defenses in shambles, the residents of St. Augustine were left vulnerable to further attacks. Governor Menéndez Márquez and his soldiers eventually returned to the smoking remains of the settlement, but they were powerless to retaliate against Drake’s fleet, which had already set sail back to England, having accomplished its mission of plunder and destruction.

Drake’s raid on St. Augustine was one of the most significant attacks on Spanish territory during the period of European colonization in the Americas. For Spain, it was a humiliating defeat, exposing the vulnerability of its far-flung empire to English privateers and other hostile powers. The raid also demonstrated the growing threat that England posed to Spain’s dominance in the New World, and it marked a turning point in the ongoing conflict between the two nations.

Despite the devastation, the Spanish were determined to maintain their presence in Florida. St. Augustine was quickly rebuilt, although it took years for the settlement to fully recover from the destruction caused by Drake’s raid. Spain reinforced the town’s defenses, eventually constructing the Castillo de San Marcos, a massive stone fortress designed to withstand future attacks. The fort, which still stands today, became a symbol of Spain’s determination to hold on to its Florida colony, even in the face of repeated English and French attempts to seize it.

For Sir Francis Drake, the raid on St. Augustine was just one chapter in his long and storied career as a privateer and explorer. After returning to England, he was hailed as a hero for his exploits in the Americas, and his actions helped solidify his reputation as one of the greatest naval commanders of his time. Two years later, in 1588, Drake would play a key role in the defeat of the Spanish Armada, a victory that cemented England’s naval supremacy and marked the beginning of Spain’s decline as a global power.

Today, Drake’s raid on St. Augustine is remembered as a key moment in Florida’s early history. The attack was a stark reminder of the dangers faced by European settlers in the New World, where rival nations, privateers, and hostile indigenous groups all vied for control of the land and its resources. The raid also highlights the broader geopolitical struggles that shaped the history of the Americas during the age of exploration, as European powers fought for dominance over newly discovered territories.

While St. Augustine survived Drake’s attack, the memory of that fiery day in 1586 still lingers. The city, now a popular tourist destination and historical site, bears the scars of its turbulent past, with landmarks like the Castillo de San Marcos serving as a testament to the resilience of its inhabitants. Drake’s raid, though long past, remains an important chapter in the story of St. Augustine and the broader history of Florida.

Sources:

• Arana, Luis R., and Albert C. Manucy. The Building of Castillo de San Marcos. U.S. National Park Service, 2000.

• Marley, David. Wars of the Americas: A Chronology of Armed Conflict in the Western Hemisphere. ABC-CLIO, 1998.

• Hoffman, Paul E. Florida's Frontiers. Indiana University Press, 2002.

• Lyon, Eugene. The Enterprise of Florida: Pedro Menéndez de Avilés and the Spanish Conquest of 1565-1568. University Press of Florida, 1976.