05/29/2026
On this day in 1586, St. Augustine was the setting for an attack from the infamous English privateer, Sir Francis Drake. To the Spanish, he was known as El Draque or “The Dragon.” 🐉
Drake was on his way to the English colony of Roanoke, and on his journey north, he spotted the small settlement of St. Augustine. At this time, the Spanish colony of St. Augustine was only 21 years old and Spain and England were engaged in the Anglo-Spanish War. Drake had heard of events that the Spanish carried out against the French Protestants and being Protestant himself, Drake decided to carry out a strategic and symbolic attack on St. Augustine and the Spanish empire.
Drake arrived off the coast of Florida on May 27, with 23 ships and roughly 1,000 men, whereas the Spanish at the time had fewer than 100 soldiers in St. Augustine. Governor Pedro Menendez Marquez ordered everyone in the city to flee into the woods to avoid the attack. When Drake landed Fort San Juan, a wooden fort, was easily taken with little fight. Inside the fort, Drake came across a chest full of gold which was the garrison’s payroll. He took the gold and ordered the fort be burned down. From the fort, Drake and his men ventured into the abandoned buildings of St. Augustine, pillaging and plundering the city. On their way out of town, they burned the city and all the crops to the ground.
Upon hearing of the attack, the Timucan chieftainness, Dona Maria, whose village was located at the Nombre de Dios Mission, ordered each family in her village to give 25 pounds of corn to send to the people of St. Augustine who had lost everything and were facing mass starvation. The Timucan people ended up sending 1,200 pounds of food and saved the residents.
The legacy of Drake’s Raid continues today in St. Augustine through re-enactments and the layers of charcoal and burned artifacts dating back to the raid which are discovered during archaeological digs.
Photo: Sir Francis Drake and 1589 Baptista Boazio map of St. Augustine.
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