Sir Francis Drake, scourge of the Spanish Main, came to Florida and destroyed St. Augustine in 1586. Judging from other battles that took place during Drake’s swing through Spain’s Caribbean empire, the Florida episode was a relatively minor affair. St. Augustine at the time was a small out-of-the-way village of about 300 persons with its only defense the small outpost, San Juan de los Pinillos. In contrast to the splendid buildings, numerous soldiers, and excellent defenses of Santo Domingo and Cartagena, St. Augustine was not very important. But in defensive tactics and in its use of manpower, the Florida town showed to good advantage; in some ways it utilized its limited defensive power more effectively than the two larger and more strongly fortified places.
Covington, James W.
"Drake Destroys St. Augustine: 1586,"
Florida Historical Quarterly: Vol. 44
, Article 9.
Available at: https://stars.library.ucf.edu/fhq/vol44/iss1/9