Today, the Florida State Quarter Coin tells the story of the exploits on the south eastern coast 429 years ago.
In the History of Saint Augustine, Florida published in 1881, William W. Dewhurst described the actions of Sir Francis Drake on May 8, 1586:
Sailing in September, 1585, there arrived soon after in the West Indies a fleet of twenty-six vessels which had been fitted out by private persons in England to cruise against the Spanish commerce, and placed under the command of Sir Francis Drake, with the vice-admirals Frobisher and Knolles.
After sacking St. Jago, raising a contribution of twenty-five thousand ducats on St. Domingo, and doing great injury to the Spanish shipping in the Caribbean Seas, they steered for Florida on their homeward voyage.
Passing up the coast when abreast Anastatia Island, on the 8th of May, 1586, they sighted a tower or look-out station on the shore.
Satisfied that it was some Spanish station the admiral ordered the boats manned and landed a body of troops on the island. Advancing toward the look-out, they perceived across the bay a fort, and further up a town built of wood.
In defiance of King Philip’s order prohibiting foreigners, on pain of death, from setting foot in the province of Florida, the admiral sent General Carlisle, of the land forces, with a small body of soldiers to enter the town.
The sentinel on the island had probably retreated to the fort, as the Spaniards, without parley, opened fire upon the English boat as soon as it came within range of their guns.
Perceiving that the Spaniards intended to oppose his landing, and having too small a force to make an attack upon the fort, General Carlisle withdrew to the vessels which were anchored off the bar.
That evening a small boat was observed approaching the fleet from across the bay. As the boat came near, the music of a fife was heard, and the breeze bore to the ears of the English the familiar notes of the Prince of Orange’s march.
The fifer proved to be a French musician who had been captured, probably with Ribault’s men, and who had taken advantage of the panic which the presence of the English fleet was then causing, to make his escape.
He reported that the fort had been abandoned, and offered to conduct the English to the town.
In the morning Sir Francis crossed the bay, and finding the fort deserted, as the Frenchman had reported, he took possession of the same and hoisted the English flag.
The fort at that time was called San Juan de Pinos, and was but a rude structure built of logs and earth, and without a ditch.
The palisades were built of cabbage palmettoes driven in the ground.
The platforms were constructed by laying the bodies of pine trees horizontally on each other, and filling an intervening space with earth well rammed.
Upon these platforms were mounted fourteen brass cannon, of what caliber is not mentioned. The garrison numbered one hundred and fifty soldiers.
Their retreat had been so precipitous that they neglected to remove the paymaster’s funds, and a chest containing ten thousand dollars in silver fell into the hands of the English. It is to be hoped that this unsoldierly conduct met with exemplary correction at the hands of the corregidors, after the British sailed away.
Whether the massive, iron-bound mahogany chest still (1858) preserved in the old fort is the same which fell into the hands of Drake, is a question for antiquarians to decide; its ancient appearance might well justify the supposition.
The next day the English marched toward the town; but it is said that they were unable to proceed by land, owing to heavy rains having lately fallen, and therefore returned to the fort and embarked in boats.
Proceeding up the sound, as the boats approached the town, the Spaniards made a show of resistance; but, on the first discharge from the British marines, they fled into the country, leaving the town at the mercy of the invader.
After pillaging the town and destroying the gardens, Sir Francis Drake made no further delay, but continued on his voyage to England.
The Spanish account says he burned the town in revenge for the killing of his sergeant-major.
The place and this attack were considered of so much importance, that after the arrival of Sir Francis in England, an engraving of “Drake’s descent upon St. Augustine” was made, which “represents an octagonal fort between two streams; at the distance of half a mile, another stream; beyond that the town with a look-out and two religious houses, one of which is a church and the other probably the house of the Franciscans, who had shortly before established a house of their order there.
The town contains three squares lengthwise and four in width, with gardens on the west side.
Some doubt has been thrown on the actual site of the first settlement by this account; but I think it probably stood considerably to the south of the present public square, between the barracks and the powder-house.
Perhaps Maria Sanchez (Santa Maria) Creek may have then communicated with the bay near its present head, in wet weather and at high tides isolating the fort from the town. The present north ditch may have been the bed of a tide creek, and thus would correspond to the appearance presented by the sketch.
It is well known that the north end of the city has been built at a much later period than the southern, and that the now vacant space below the barracks was once occupied with buildings.
Buildings and fields are shown on Anastatia Island, opposite the town. The relative position of the town, with reference to the entrance of the harbor, is correctly shown on the plan, and there seems no sufficient ground to doubt the identity of the present town with the ancient locality.
The Florida State Quarter Coin shows against a view of the Castillo de San Marcos, a fort begun in 1672 that was more robust than the fort found by Sir Francis Drake.