The Caribbean Raid
Drake's next exploit marks a further step on the road to outright war between England and Spain. This was the West Indies raid of 1585-1586, which showed that the Spaniards were almost as poorly prepared for defense on their Atlantic coasts as on the Pacific.
Drake's fleet of seven large ships and 22 smaller vessels sailed from Plymouth on September 14th, 1585; stopped at Bayona and Vigo on the northwest coast of Spain (Oct. 1-11), and reached Santiago in the Cape Verde Islands on November 17th. That town was plundered and burned, and on November 29th the fleet set sail across the Atlantic. On New Year's Day, 1586, they reached Santo Domingo, which was captured and plundered, and a 25,000 ducat ransom extorted. On February 9th Cartagena was captured, and was occupied until March 26th. Here again the town was plundered, and a ransom of 110,000 ducats was collected. Thence they sailed north across the Caribbean to the coast of Florida, where St. Augustine was captured and destroyed (May 28-30). Drake reached England again on July 22nd, when he sailed into Portsmouth.
Baptista Boazio, an Italian artist resident in London, made engravings of the attacks on Santiago, Santo Domingo, Cartagena, and St. Augustine. He must have obtained drawings from a participant, perhaps from Drake himself. In each case these are the first published views or plans of the respective localities. Boazio's engravings appeared in two different editions, one measuring c.205 x 300 mm., the other c.405 x 520 mm. The smaller engravings bear captions in Latin and French, and may have appeared in 1588; the larger ones, with Latin captions, and pasted-on English texts, appeared in 1589, in London (see pages 123-127).
A narrative of the expedition was written by one of the participants, Walter Bigges; following his death at Cartagena it was continued by Lieutenant Croftes. In this collection are the first Latin edition, 1588; the first English edition (R. Field, 1589); the second English edition (R. Ward, 1589)   .
The Bigges narrative also appears in Hakluyt, second edition, III, pages 534-548 .
The Boazio view-plan of St. Augustine, reproduced opposite from a copy in the collection, is famous as the first representation surviving of any North American city (north of Mexico, that is), and as the first publication of any of the John White drawings of Virginia, namely the picture of the Dorado fish (lower left on the engraving).
John White (fl. 1585-1593) is noted as the artist who made the earliest pictorial record of Virginia and its native inhabitants. He was there twice, first in the Ralegh settlement of 1585, returning to England with Drake in 1586. In the second attempt at settlement, White went to Virginia as Governor in 1587, returning to England that same year to secure further supplies for the colony. He went again to Virginia in 1590, only to find that the settlement had disappeared, presumably wiped out by the Indians.
In 1590 there appeared the first part of De Bry's Grands Voyages , which was Hariot's Brief and True Report of the new found land of Virginia , illustrated with engravings after the paintings which White had made in Virginia. These engravings are to be seen in the German edition of De Bry in this collection . White's narrative of his last voyage to Virginia, prefaced by a letter to Hakluyt, is printed in the second edition of Hakluyt, III, pp. 287-295 .
Drake's awareness of the progress of contemporary colonization caused him to linger in America even after his destructive raid on the Spanish colony in Florida. Despite contrary winds he called at Roanoke Island, North Carolina, in June 1586, to inquire about the welfare of the Virginia settlers sent out in an expedition commanded by Richard Grenville in 1585. This was implementing a project drawn up by Richard Hakluyt and patronized by Walter Ralegh. The colonists, under their governor Ralph Lane, were suffering from conflicts with the Indians and stood in sore need of supplies which were to arrive, too late, with Grenville; so they preferred to accept Drake's humane offer of a passage home. Drake thereupon took along not only most of the original drawings of John White and other invaluable evidence about mainland North America, but also tobacco, as Camden related:
... these men which were brought backe, were the first that I knew of that brought into England that Indian plant, which they call Tabacca and Nicotia, and use it against crudities, being taught it by the Indians. Certainely from that time, it beganne to be in great request, and to be sold at an high rate, whilst very many everywhere, some for wantonnesse, some for healthe, suck in with insatiable greedinesse the stinking smoke thereof, through an earthen pipe, and presently snuffe it out at their nostrils: Insomuch as Tabacca shops are kept in Townes every where, no lesse than tap-houses and tavernes ...
Don Pedro Vique Manrique took part in the defense of Cartagena against Drake on February 9th, 1586. He later fell into the clutches of the law on charges of extortion. An unrecorded and possibly unique legal paper, printed during the course of the prosecution against him, gives details of his defense of Cartagena, which he offered in extenuation of his crimes.
The very important unpublished source document, the title leaf of which is reproduced on the next page, is entirely in the handwriting of Don Alonso Pérez de Guzmán el Bueno, seventh Duke of Medina Sidonia (1550-1615), best known for his unsuccessful leadership of the Spanish Armada of 1588. It is dated 1586, and comprises the title and 10 folio pages of his writing. It relates to Drake's depredations and to the measures to be taken to avert further such disasters. It recommends a thorough overhaul of Spanish naval strategy both on the Pacific and Atlantic coasts.
The Diego Maldonado whose memorandum is here reviewed by Medina Sidonia was one of the most experienced mariners in the Spanish naval service. He commanded the annual convoys to New Spain or the Spanish Main four times between 1575 and 1583. It is evident that Medina Sidonia is sometimes agreeing with Maldonado's recommendations, at other times giving different or supplementary advice.
Among the subjects discussed are: the navigation of the Strait of Magellan, and the best time to make shipments of treasure from Peru, so as to avoid any raiders who might get through the Strait; naval strength available for the defense of the Spanish Main (the Caribbean); methods for the shipment of artillery and related munitions to America; shipbuilding in America.
Medina Sidonia refers to the Drake raid on the West Indies in his remarks on Cartagena; he states that galleys had been adequate for coastal defense before Drake's arrival, and their lack of success against Drake may have been the result of poor handling.
In one paragraph, Medina Sidonia proposes that a fleet be built up to enter the English Channel and to threaten England. This remarkable anticipation of the 1588 Armada scheme may have been significant in Medina Sidonia's appointment to the command of that campaign.
All in all, this document shows in the clearest way the profound changes which were being forced upon the Spanish government in response to the Drake system of spirited attack-a sort of naval blitzkrieg.
Medina Sidonia's title (translated) reads:
Reply to the memorandum given to His Majesty by Don Diego Maldonado in the matter of the South Sea [Pacific Ocean]. Sent October 25, 1586.
This is followed by Medina Sidonia's filing instruction (trans.):
Miscellaneous orders, 1586 and his initials.