Military Wiki
Raid on St. Augustine
Part of the Anglo–Spanish War
Boazio-Sir Francis Drake in St. Augustine.jpg
Sir Francis Drake in St. Augustine 1586 hand-colored engraving, by Baptista Boazio, 1589
Date27–29 May 1586
LocationSt. Augustine, Spanish Main
(Present day Florida)
Result English victory[1]


  • Apalachee Indians
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 was captured in 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 the 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.


A map of Drake's voyage to the Spanish Main

War had been 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 in a kind of preemptive strike. Sailing from Plymouth, England, he struck at the Spanish new world city of Santo Domingo on 1 January 1586 and following that successfully attacked on 19 February the important city of Cartagena.[1][4]

Drake wanted to strike at another Spanish city on the Main before finally visiting and replenishing Sir Walter Raleigh's new colony of Roanoke Colony on the American East Coast. Then 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 and his men dug wells in search of fresh water and gathered supplies to help counter an outbreak of dysentery after which he moved on.[2]

The fleet traveled north within sight of land on the Florida peninsula sailing past the West 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, and the oldest permanent colonial settlement in North America.[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]


Sir Francis Drake

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 Carleill and a few volunteers rowed a ship's boat into the inlet and there was 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]

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 attacked, launched by native allies of the Spanish garrison. 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 across a 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 found intact a 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 beyond the in the outskirts, when Drake's men arrived, and they opened up a skirmishing fire. Anthony Powell one of Carleill's deputies 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 leaving Drake in control of the settlement.[2][5]


A 1584 map of the Roanoke colony

The English garrisoned it 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 by the English among other booty.[3][6]

Once the English had gone Menéndez and the rest of the Spanish settlers returned to find a smoldering ruins and very little left. He soon and begged for help from the viceroy of Cuba and the settlement took a while to build it self back up. The destroyed fort was replaced with the present day Castillo de San Marcos.[3]

Drake's fleet sailed from St. Augustine on 29 May, heading northwards up the coast, looking for signs of Raleigh's settlement. They looked 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 the Roanoke Island. He had no supplies but offered to take any of the settlers back and reached England on July 22, when he sailed into Portsmouth.[3]


The consequences of Drake's raid to the Spanish were significant. 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 the Spanish king, Philip II, that all concentration should be in one place and that being 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]

By now news had reached most of Europe to that fact that Drake had made this raid. When he arrived in England he became a national hero. In Spain the news was a disaster and this now further buoyed a Spanish invasion of England by King Philip.[7]


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 reenactments and all are held in the old part of town.[8]

See also


  1. 1.0 1.1 1.2 Jacques p.877
  2. 2.0 2.1 2.2 2.3 2.4 2.5 2.6 2.7 Konstam p.66-70
  3. 3.0 3.1 3.2 3.3 Marley p.629
  4. 4.0 4.1 4.2 4.3 Sugden p.189-90
  5. 5.0 5.1 5.2 Johnson p.10-15
  6. 6.0 6.1 6.2 6.3 Rowland p.45
  7. Konstam p.76-77
  8. Drakes Raid

External links


  • Jaques, Tony (2006). Dictionary of Battles and Sieges: A Guide to 8500 Battles from Antiquity Through the Twenty-first Century. Greenwood Press. ISBN 978-0313335365. 
  • Johnson, Betty Drees (1961). A Survey of Sir Francis Drake's Raid on St. Augustine, Florida, 1586. University of Stetson. 
  • Marley, David (2005). Historic Cities of the Americas: An Illustrated Encyclopedia. ABC-CLIO. ISBN 1576070271. 
  • Sugden, John (2004). Sir Francis Drake. Penguin Books. ISBN 978-1844137626. 
  • Konstam, Angus (2011). The Great Expedition: Sir Francis Drake on the Spanish Main - 1585-86 (Raid). Osprey Pub. ISBN 978-1849082457. 
  • Graham, Winston (1987). Spanish Armadas. Barnes & Noble. ISBN 978-0880291682. 
  • Rowland, Lawrence S. (2005). The History of Beaufort County, South Carolina: 1514-1861. 1. History Press. ISBN 978-1596290273. 

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