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Sir Francis Drake

St. Augustine Under Three Flags: Tourist Guide and History


The settlement work outside of St. Augustine advanced but slowly, mainly consisting of garrisons and missions established at various points. At this period (1586) relations between Spain and England were strained, Philip was gathering together all his strength by land and sea for the invasion of England, and Elizabeth was using every means in her power to retard the Spanish preparations. Her most effective method was the granting to various sea captains commissions to capture and destroy all Spanish property in the new world. Among these was Sir Francis Drake, who in six voyages had captured immense booty from the treasure ships of Spain and from towns on the Spanish main and the West India Islands, thus serving his country and enriching himself. Everywhere he was successful and his name became a terror to Spanish mariners.

In 1585 Drake with a fleet of twenty-one ships sailed for the Spanish main, plundering many towns and adding immensely to his own wealth. After which he sailed west. On May 28, 1586, he sighted a lookout the Spaniards had built on Anastasia Island. He immediately sent a boat to reconnoiter, which reported a Spanish town and fort located on the mainland. Putting a gun in his pinnace he took up a position opposite the fort and opened fire. The first shot struck through the Spanish flag. Drake wished to cross to the mainland and begin an attack at once, but his men refused to accompany him. During the night the Spaniards abandoned the fort. Drake, learning of this, at once crossed the bay to the fort. Lieutenant Cates, one of Drake's officers, writes:

"When the day appeared we found it built all of timber, the walls being non other but whole mastes or bodies of trees set upright and close together in manner of a pale, without any ditch as yet made, but wholly intended with some more time; for as yet they had not finished all their worke….The Platforme whereon the ordinance lay was whole bodies of long pine trees, whereof there is a great plenty, layd across one on another and some little earth amongst. There were in it thirteen or fourteen great pieces of brass ordinance and a chest unbroken up, having in it the value of some two thousand pounds sterling of the King's treasure, to pay the soldiers of that place who were a hundred and fiftie men. The fort thus won which they called St. John's fort (San Juan de Pinos) and the day opened we assayed to goe to the town but could not by reason of some rivers and broke ground which was between the two places; and therefore being enforced to embark again into our pinnaces, we went thither upon the great maine river, which is called as also the town by the name of S. Augustin. At our approaching o land, there were some that began to show themselves, and to bestow some few shots upon us, but presently withdrew themselves and in their running thus away, the Sergeant-Major, finding one of their horses ready saddled and bridled, tooke the same to follow the chase' and so overgoing all his companie was, by one third layd behind a bush shotte through the head, and falling down therewith, was by the same and two or three more stabbed in three or four places of his body with swords and daggers before an could come neare to his rescue."

Taking what valuable they could find in the town they burned the place and also the fort. Drake now sailed direct to Roanoke Island and thence direct to Plymouth, carrying the first consignment of tobacco to England.

Excerpt from "St. Augustine Under Three Flags: Tourist Guide and History" W. J. Harris Company, 1918, pp. 6–7.


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