Five years after leading the first English circumnavigation of the globe in 1577–1580, Sir Francis Drake led a raid against Spanish settlements in the Caribbean including Santiago, Santo Domingo, and Cartagena, as well as St. Augustine (in present-day Florida). This engraving, by Baptista Boazio, was made to accompany a book describing Drake’s 1586 expedition, A Summarie and True Discourse of Sir Francis Drake’s West Indian Voyage (published in 1588–1589). The illustration depicts the attack of Drake’s fleet of twenty-three ships on St. Augustine, which was captured and destroyed on May 28–30, 1586. Although Boazio was not on the voyage, he worked from firsthand accounts. The engraving is the earliest known surviving view of a New World city north of Mexico.
Drake operated as a privateer under a “letter of marque and reprisal” issued by Queen Elizabeth I. His operations were part of the long-standing and escalating tensions between Protestant England and Catholic Spain. The Boazio illustrations and A Summarie and True Discourse of Sir Francis Drake’s West Indian Voyage were published following the English victory over the Spanish Armada in 1588.