Five years after leading the first English circumnavigation in 1577–1580, Sir Francis Drake attacked Spanish settlements in the Caribbean, including Santiago, Santo Domingo, and Cartagena, as well as St. Augustine (in present-day Florida). This engraving by Battista Boisio was made as part of a book describing Drake's expedition of 1586. Although Boisio was not on the voyage, he was working from first-hand accounts. The engraving is the earliest known surviving view of a New World city north of Mexico.

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