This map, one of the earliest maps of a city that is now in the United States, depicts the June 1586 attack on St. Augustine by Sir Francis Drake. Note, in the middle, the English troops on Anastasia Island firing across the water on the Spanish fort.
Florida and the Pirates
On May 28, 1668, a ship anchored off St. Augustine harbor. It was a vessel from Veracruz, bringing flour from México. In the town, the drum sounded the alert for the garrison of 120 men. A launch went out to identify the newcomer and put the harbor pilot aboard. As it neared the ship, the crew on the launch hailed the Spaniards lining her gunwale. To the routine questions came the usual answers: Friends from México—come aboard! Two shots from the launch told the town the ship had been identified as friendly, and the seamen warped the launch alongside the ship. In St. Augustine, the people heard the signal shots and rejoiced. The soldiers returned their arms to the main guardhouse on the town plaza. Tomorrow the supplies would come ashore.
Unknown to the townspeople, when the launch pilot stepped aboard the supply ship, an alien crew of pirates swarmed out of hiding and leveled their guns at him and the others. He could do nothing but surrender.
Some time after midnight, a corporal was out on the bay fishing when he heard the sound of many oars pulling across the water. Something was not right. Desperately he paddled his little craft toward shore. The pirates, four boatloads of them, were right behind. Twice their shots found their mark, but he got to the fort where his shouts aroused the guards.
At the main guardhouse, a quarter mile from the fort, the sentries heard the shouting and the gunfire, but before they could respond, the pirates were upon them, a hundred strong. Out-numbered, the guards ran for the fort. Gov. Francisco de la Guerra rushed out of his house and, with the pirates pounding at his heels, joined the race for the fort. Somehow the garrison was able to beat back several assaults. In the confusion of darkness, however, the pirates seemed to be everywhere. They destroyed the weapons they found in the guardhouse and went on to the government house. Shouting and cursing, they scattered through the narrow streets, seizing or shooting the frightened, bewildered inhabitants.
Sgt. Maj. Nicolás Ponce de Léon, the officer responsible for defending the town, was at home, a sick man, covered with a greasy mercury salve and weak from the “sweatings” prescribed for his illness. On hearing the din, he roused himself and rushed to the guardhouse, only to find the pirates had been there first. He turned to the urgent task of shepherding his 70 unarmed soldiers and the others—men, women, and children—into the woods, leaving the pirates in complete possession of the town.
By daybreak the little force at the fort had lost five men, but they believed they had killed 11 pirates and wounded 19 others. Ponce came from the woods and reinforced the fort with his weaponless men. With daylight, two other vessels joined the ship from Veracruz. One was St. Augustine’s own frigate, taken by the raiders near Havana, in which the pirates had been able to move in Spanish waters without detection. The other was the pirates’ own craft. All three sailed into the bay, passed the cannon fire of the fort, anchored just out of range, and landed their remaining forces. Systematically they began to sack the town; no structure was neglected.
That afternoon, the governor sent out a sortie from the fort, but the leaders were wounded and the party retired. After 20 hours ashore, however, the pirates were ready to leave anyway, taking their booty, which probably amounted to only a few thousand pesos, and about 70 prisoners whom they had seized during the previous night’s rampage. Just before leaving they ransomed most of their prisoners for meat, water, and firewood. The local Indians, however, they kept, claiming that the governor of Jamaica had told them to keep all Indians, blacks, and mulattoes as slaves, even if they were Spanish freemen. Finally on June 5 the raiders headed out to sea, amused as once again they passed the thunder of the useless guns in the old wooden fort as the small community grieved over its 60 dead and gave thanks for the ransomed prisoners.
The released prisoners identified the invaders as English and told how the enemy had carefully sounded the inlet, taken its latitude, and noted the landmarks. They intended to come back and seize the fort and make it a base for future operations against Spanish shipping.