The present view of Santo Domingo in the Dominican Republic (together with views of San Augustine, Florida, Santiago in the Cape Verde Islands and Cartagena in Columbia) were drawn, and probably engraved, by the Italian artist Baptista Boazio.

The Boazio views are "probably the most interesting and important published graphic work pertaining to Drake and his career" (Kraus). They are also the first representations of those four cities. Indeed, the view of San Augustine is the first known engraving of any locality in the present-day United States. Having famously circumnavigated the globe between 1577 and 1580, Sir Francis Drake voyaged to North and Central America in 1585, where he ransacked many of the towns shown in Boazio's engravings. There is no evidence of Boazio's participation in any voyage to the New World, but he must have obtained a version of these views from someone who had travelled across the Atlantic. In fact, Kraus believes that the plan's sea creatures, at least, were taken from original drawings by John White, the Governor of the first English settlement in America, who along with the other surviving settlers returned to England from Roanoke Island with Drake's expedition.

Two issues of these views were printed in Leiden in 1588, both extremely rare: a large paper issue (16.5 by 22 inches), printed to illustrate Walter Bigges and Master Croftes', 'A Summarie and true discourse of Sir Francis Drake's West Indian Voyage', published in London in 1589, and the present smaller size (7.5 by 11.25 inches), which has captions in Latin and French, a numerical instead of alphabetical key, and was probably printed to illustrate the Latin and French translations of the same work, published in Leiden in 1588. While the pictures are broadly similar, the present examples show greater detail, whilst the larger ones include more sea monsters and other embellishments.

Priority regarding the date of publication between the two issues has not yet been established with certainty, but there are indications that the present, smaller issue came first:
"A close comparison of details, however, suggests that the smaller engravings come from an earlier set of drawings and that the larger maps represent revisions as well as embellishments, probably done by the same artist" (Mary Frear Keeler).
There were two subsequent issues of the smaller Boazio plates: the first in 1589, published in Cologne, used the same plates but with only the Latin text below and further printed text to the verso; the second in 1590, published in Nuremberg, was either printed from new plates or the plates have been heavily revised.

In 1970, Kraus estimated that they were eight recorded complete sets of the large Boazio plates and seven complete sets of the smaller plates (p156). Only one complete set of the four large views has appeared in the last fifty years, in the DuPont sale at Christie's in 1991 for $231,000; there is no record of any copy of the 1588 smaller size issue having gone through auction OCLC records eight complete sets of the former held in institutions, and only two complete sets of the small 1588 plates, held at the New York Public Library and the Huntington Library. There is also an incomplete set (lacking San Augustine) in the Kraus' Sir Francis Drake Collection housed in the Library of Congress.