History Resources

Sir Francis Drake’s attack on St. Augustine, 1586

A Spotlight on a Primary Source by Baptista Boazio

Baptista Boazio, Drake’s attack on St. Augustine, Florida, May 28–30, 1586. (Rare Books and Special Collections Division, Library of Congress, G3291.S12 s000 .B6)

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.

Questions for Discussion

Read the introduction, view the three images, and review the sheet with notations lettered A–P. Then apply your knowledge of world and American history to answer the questions that follow.

Note: The definitions asked for in Question 1 may be obtained from a reputable history site on the Internet. In addition, access to a map of the southeastern region of the United States, the Caribbean, and the West Indies will be helpful in answering Question 2.

  1. Sir Francis Drake is described as a “privateer” operating under a “letter of marque and reprisal.” Research the meaning of these terms and then use the definitions to describe Sir Francis Drake’s responsibilities and motives.
  2. Locate St. Augustine in relation to North America, the Caribbean, and the West Indies. Use that knowledge to explain why Queen Elizabeth I ordered a raid upon that town. In addition to geographic consideration, what other reasons did England have for attacking Spanish territory?
  3. According to the information provided in the notation sheet, how well prepared were the Spanish for a possible attack?
  4. Carefully review the three maps. From the information they provide, put together your own description of how the English attacked St. Augustine.

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