Raid on St. Augustine

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Raid on St. Augustine
Part of the Anglo–Spanish War
Baptista Boazio's Map of Sir Francis Drake's Raid on St. Augustine (published in 1589) (8879100326).jpg
Sir Francis Drake in St. Augustine 1586 hand-colored engraving, by Baptista Boazio, 1589
Date27–29 May 1586
Location St. Augustine, Florida
(Region of the Spanish Main)
Result English victory [1]

Flag of Cross of Burgundy.svg Spain

Flag of England.svg England
Commanders and leaders
Governor Pedro Menéndez de Márquez Francis Drake
Christopher Carleill
100 soldiers & militia
Unknown number of Indians
2 forts [2]
23 ships,
19 support vessels & prizes,
1,000 troops [3]
Casualties and losses
35 killed or wounded [4] Light

The Raid on St. Augustine was a military event during the Anglo-Spanish War in which the Spanish settlement of St. Augustine in Florida (Spanish : San Agustín)) was captured in a small fight and burnt by an English expedition fleet led by Francis Drake. [1] This was part of Francis Drake's Great Expedition and was his last engagement on the Spanish Main before Drake headed north for the Roanoke Colony. The expedition also forced the Spanish to abandon any settlements and forts in present-day South Carolina.

Anglo-Spanish War (1585–1604) 1585–1604 war between the kingdoms of Spain and England

The Anglo-Spanish War (1585–1604) was an intermittent conflict between the kingdoms of Spain and England that was never formally declared. The war was punctuated by widely separated battles, and began with England's military expedition in 1585 to what was then the Spanish Netherlands under the command of the Earl of Leicester in support of the resistance of the States General to Spanish Habsburg rule.

St. Augustine, Florida City in Florida, United States

St. Augustine is a city in the Southeastern United States, on the Atlantic coast of northeastern Florida. Founded in 1565 by Spanish explorers, it is the oldest continuously inhabited European-established settlement within the borders of the continental United States.

Spanish Florida Former Spanish possession in North America

Spanish Florida, was the first major European land claim and attempted settlement in North America during the European Age of Discovery. La Florida formed part of the Captaincy General of Cuba, the Viceroyalty of New Spain, and the Spanish Empire during Spanish colonization of the Americas. While its boundaries were never clearly or formally defined, the territory was much larger than the present-day state of Florida, extending over much of what is now the southeastern United States, including all of present-day Florida plus portions of Georgia, Alabama, Mississippi, South Carolina, and southeastern Louisiana. Spain's claim to this vast area was based on several wide-ranging expeditions mounted during the 16th century. A number of missions, settlements, and small forts existed in the 16th and to a lesser extent in the 17th century; eventually they were abandoned due to pressure from the expanding English and French colonial projects, the collapse of the native populations, and the general difficulty in becoming agriculturally or economically self-sufficient. By the 18th century, Spain's control over La Florida did not extend much beyond its three forts, all located in present-day Florida: St. Augustine, St. Marks, and Pensacola.



A map of Drake's voyage to the Spanish Main Boazio-Sir Francis Drakes West Indian Voyage.jpg
A map of Drake's voyage to the Spanish Main

War had already been unofficially declared by Philip II of Spain after the Treaty of Nonsuch in which Elizabeth I had offered her support to the rebellious Protestant Dutch rebels. The Queen through Francis Walsingham ordered Sir Francis Drake to lead an expedition to attack the Spanish New World colonies in a kind of preemptive strike. Sailing from Plymouth, England, in November 1585 he struck first at Santiago in the Cape Verde islands off the northwest coast of Africa, then across the Atlantic at the Spanish city of Santo Domingo which was captured and ransomed on 1 January 1586; following that he successfully attacked the important city of Cartagena on 19 February. [1] [4]

Philip II of Spain 16th-century King of Spain who became King of England by marriage

Philip II was King of Castile and Aragon (1556–98), King of Portugal, King of Naples and Sicily, and jure uxoris King of England and Ireland. He was also Duke of Milan. From 1555 he was lord of the Seventeen Provinces of the Netherlands.

The Treaty of Nonsuch was signed on 19 August 1585 by Elizabeth I of England and the Dutch Rebels fighting against Spanish rule. It was the first international treaty signed by what would become the Dutch Republic. It was signed at Nonsuch Palace, Surrey, England.

Dutch Revolt war in the 16th century

The Dutch Revolt (1568–1648) was the revolt of the northern, largely Protestant Seven Provinces of the Low Countries against the rule of the Roman Catholic Habsburg King Philip II of Spain, hereditary ruler of the provinces. The northern provinces (Netherlands) eventually separated from the southern provinces, which continued under Habsburg Spain until 1714.

Drake wanted to strike at another Spanish city on the Spanish Main before finally visiting and replenishing Sir Walter Raleigh's new colony of Roanoke Colony on the American east coast. After this he hoped to make the transatlantic crossing back to England. The fleet headed north, and in late April Drake put into the Spanish Cuban mainland where his men dug wells in search of fresh water and gathered supplies to help counter an outbreak of dysentery, then he moved on. [2]

Walter Raleigh English aristocrat, writer, poet, soldier, courtier, spy, and explorer

Sir Walter Raleigh, also spelled Ralegh, was an English landed gentleman, writer, poet, soldier, politician, courtier, spy and explorer. He was cousin to Sir Richard Grenville and younger half-brother of Sir Humphrey Gilbert. He is also well known for popularising tobacco in England. Raleigh was one of the most notable figures of the Elizabethan era.

Roanoke Colony Former colony in present-day Dare County, North Carolina, United States

The Roanoke Colony, also known as the Lost Colony, was the first attempt at founding a permanent English settlement in North America. It was established in 1585 on Roanoke Island in what is today's Dare County, North Carolina. The colony was sponsored by Sir Walter Raleigh, although he himself never set foot in it.

Dysentery inflammation of the intestine causing diarrhea with blood

Dysentery is an inflammatory disease of the intestine, especially of the colon, which always results in severe diarrhea and abdominal pains. Other symptoms may include fever and a feeling of incomplete defecation. The disease is caused by several types of infectious pathogens such as bacteria, viruses and parasites.

The fleet traveled north within sight of land on the Florida peninsula sailing past its eastern coast. On 27 May 1586 as they approached further north a small fort was spotted on the shore, with a small inlet close by. This was the location of St Augustine, the most northerly town in Spain's New World Empire. [2] Drake knew of the place and was also aware of the fact that the Spanish under Pedro Menéndez de Avilés had ordered all of the French Huguenot colonists that had tried to settle in the area executed. Drake decided on one final opportunity to raid and plunder, and a chance to avenge his fellow Protestants. [4]

Pedro Menéndez de Avilés Spanish explorer

Pedro Menéndez de Avilés was a Spanish admiral and explorer from the region of Asturias, Spain, who is remembered for planning the first regular trans-oceanic convoys and for founding St. Augustine, Florida, in 1565. This was the first successful Spanish settlement in La Florida and the most significant city in the region for nearly three centuries. St. Augustine is the oldest continuously-inhabited, European-established settlement in the continental United States. Menéndez de Avilés was also the first governor of Florida (1565–74).

French Florida

French Florida was a colonial territory established by French Huguenot colonists in what is now Florida between 1562 and 1565.


The English attacked and bombarded a small wooden fort in the sand dunes; the Spanish there fired only a few shots and fled. Drake sent a landing party to investigate, while Christopher Carleill, captain of the Tiger, and a few volunteers rowed a ship's boat into the inlet and saw no sign of any Spaniards. It sat on a strip of sand, separated from the mainland by a band of water, which entered into the inlet. [2] A French Huguenot Nicholas Borgoignon, who had been taken prisoner by the Spanish six years before was found in a boat and agreed to guide the English to the Spanish settlement. [5]

Christopher Carleill English writer

Christopher Carleill was an English military and naval commander.

Sir Francis Drake Francis Drake.jpg
Sir Francis Drake

The Spanish governor of St. Augustine, Pedro Menéndez de Márquez (nephew of Pedro Menéndez de Avilés), was warned that Drake was off the coast, and he realized that with fewer than a hundred militiamen he could offer little in the way of resistance. The Spanish settlers withdrew inland and hoped to make surprise raids against the English gradually. Drake and his men occupied the area of the small fort but during the night Indians, native allies of the Spanish garrison, attacked. Drake and his men held their ground and within twenty minutes the Indians were repulsed with some loss. [2] [5]

The following day, Drake, Carleill and around two hundred men advanced up the inlet in pinnaces and small boats, and they soon came upon the Spanish log stockade fort of San Juan. After a few shots by the Spanish, the English landed and took the fort with only a few losses. They found it deserted, as the Spanish had fled, but discovered an intact gun platform with fourteen bronze artillery pieces. They also found a chest containing the garrison's pay, about 2,000 gold ducats, which was inadvertently left behind in the retreat. [2] Drake, knowing the Spanish had fled, began to plunder what he could; he took the guns, and burned the fort to the ground. [6]

Soon the English came upon the main settlement of St. Augustine itself, this time they found it deserted. The Spanish, however, were just outside the town when Drake's men arrived, and they opened up a skirmishing fire. Anthony Powell, one of Carleill's officers, was killed in the opening shots as he tried to assault the outskirts. Carleill's men then charged all the way to the outskirts of the town into the scrub, forcing the Spanish to retreat and leaving Drake in control of the settlement. [2] [5]

The English garrisoned the town overnight and the following day razed the whole of St. Augustine to the ground. All buildings were torched, crops were destroyed and anything of value was either taken or destroyed. [2] The fort of San Juan was burnt and all the artillery pieces were carried away by the English among other booty. [3] [6]


A 1584 map of the Roanoke colony Roanoke map 1584.JPG
A 1584 map of the Roanoke colony

Once the English had gone Menéndez and the rest of the Spanish settlers returned to find a smoldering ruins and very little left of their settlement. He soon begged for help from the viceroy of Cuba and the settlement took a while to build itself back up. The destroyed fort San Juan was replaced with another wooden fort. A masonry fortress to defend the presidio was not built until construction of the Castillo de San Marcos began in 1672. [3]


Drake's fleet sailed from St. Augustine on 29 May, heading northwards up the coast, looking for signs of Raleigh's settlement. They cruised into what is now Charleston Harbor but found it deserted, then continued up the coast until they saw smoke. A boat was sent to investigate, and its crew finally made contact with the English settlers, who were encamped on Roanoke Island. Drake had no supplies but offered to take any of the settlers back to England; he sailed into Portsmouth on July 22. [3]

Drake was greeted as a national hero upon his arrival in England; by that time news of his daring raids on the Spanish Main had reached most of Europe. His direct assault on the Spanish Empire was disastrous for the prestige of Spain and threatened the continued flow of New World riches, in the form of silver and gold, into its national treasury. The Spaniards, who called Drake El Draque, regarded him as a monstrous pirate. Drake's strike at the heart of the Spanish colonial empire embarrassed the Spanish king, Philip II, and hardened his resolve to invade and conquer England. [7]


The consequences of Drake's raid were significant to the Spanish. Rumors soon began to spread that the English had a settlement further north and were using the place as a base for piracy. This was confirmed by news from released Spanish prisoners that Drake had wanted to replenish the colony of Roanoke. Although the Spanish knew of Roanoke they could not find the English colony despite a number of military expeditions sent out. Menéndez came the closest reaching 37 degrees latitude but failed to find anything. [4] [6]

Fearing another raid, and with the Spanish settlements on the American West coast being overstretched, undermanned and underarmed; a crisis followed. Menéndez even conferred with the Council of the Indies in Seville (who received confirmation of St. Augustine's destruction by July) and Philip II, that all concentration should be in one place and that being at St. Augustine. Mendendez despite objections got his way and as a result Parris Island and Santa Elena were abandoned. This marked the end of the permanent Spanish presence in what today is South Carolina. [6]


In the present day the events of Sir Francis Drake's Raid are recreated in June at St. Augustine. So far there have been 27 re enactments and all are held in the old part of town. [8] The re-enactment features an encampment, drills, weapon demonstrations, and more. [9]

See also

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  1. 1 2 3 Jacques p.877
  2. 1 2 3 4 5 6 7 8 Konstam p.66-70
  3. 1 2 3 4 Marley p.629
  4. 1 2 3 4 Sugden p.189-90
  5. 1 2 3 Johnson p.10-15
  6. 1 2 3 4 Rowland p.45
  7. Konstam p.76-77
  8. Drakes Raid
  9. Drakes Raid Re-Enactment
External links