Drake’s Expedition to the West Indies Summary

  • Last updated on November 11, 2022

Drake’s expedition, which began in Spain and continued to the West Indies to plunder Spanish settlements there, initiated the Anglo-Spanish naval war and culminated in the English victory over the Spanish Armada in 1588.

Summary of Event

Relations between England and Spain during the reigns of Elizabeth I and Philip II were deteriorating because of tensions that resulted from several key factors, including colonial and commercial rivalry, English support for the Dutch Wars of Independence (1568-1648) against Philip II and Spain, Spanish involvement in plots to assassinate Elizabeth I, Spanish intervention in the French Wars of Religion (1562-1598), and Protestant-Catholic antagonism generated by the Protestant Reformation. Exploration and colonization;England of North America Drake, Francis Elizabeth I Philip II (1527-1598) Frobisher, Sir Martin Carleill, Christopher Elizabeth I (queen of England) Philip II (king of Spain) Frobisher, Sir Martin Carleill, Christopher Lane, Ralph Drake, Sir Francis

Parallel with these tensions was Drake’s participation in several key Spanish-English conflicts, including a raid in the Caribbean (1567-1569), which had ended in disaster when the Spanish fleet surprised the English at San Juan de Ulúa, a small island off Veracruz, Mexico. Also, from 1571 to 1573, Drake explored Panama and captured a mule train of Spanish silver, and while completing his circumnavigation of the globe between 1577 and 1580, Drake conducted raids on lightly defended Spanish settlements in South America and Central America. Next came smuggling and raids on Spanish shipping by the English and their attacks on Spain and its colonial possessions.

The immediate cause for the 1585-1586 expedition to the West Indies was the seizure by the Spanish of English grain ships in Spanish ports in June of 1585. In July, 1585, Elizabeth I and the English government issued orders for Drake to take a fleet to Spain to procure release of the ships and also permitted English reprisals against Spanish shipping. Elizabeth I, government officials, prominent nobles, and merchants contributed funds for the raising of the fleet in the hopes of procuring money for the government and for individual profit. Elizabeth I supplied £20,000, one half of the entire £40,000 cost of the expedition. A delay in sailing, however, was caused by the need to provision the fleet of twenty-three or twenty-five ships (the sources differ) and eight pinnaces with a crew of between sixteen hundred and nineteen hundred, with experienced sea captain and explorer Martin Frobisher as vice admiral under Drake and Christopher Carleill commander of the approximately five hundred to seven hundred troops.

Leaving the port of Plymouth on September 14, 1585, the fleet made its way toward Spain, encountering a group of French ships carrying salt. Drake confiscated the newest ship, renaming it the Drake. From September 27 until October 11, 1585, Drake’s fleet was in Vigo Bay in northwestern Spain while he discussed the seized ships with Spanish officials. The English perpetrated some minor plunder and learned that the seized ships had been released, which should have precluded additional activities by Drake’s fleet.

After Drake purchased supplies, his fleet sailed away on its “unofficial” mission—plundering Spanish settlements—while the Spanish officials scrambled to alert Spanish colonies in the Caribbean that Drake might be headed their way. Drake’s prolonged stay at Vigo Bay had aroused curiosity—was he trying to humiliate the Spanish or was he lying in wait for the Spanish treasure fleet? Ironically, the treasure fleet reached the Spanish ports safely while Drake tarried at Vigo Bay.

Drake’s fleet raided the Canary Islands and Cape Verde Islands from October 24 through November 29, 1585, burning settlements and netting supplies, including confiscated church bells, which could be melted and refashioned for military use. Drake set sail for the West Indies when, several days into the Atlantic passage, a serious illness, thought by some scholars to be a form of bubonic plague, decimated the crew, leaving several hundred dead in its wake. Upon reaching the island of Dominica in the West Indies on December 18, 1585, the crew rested, buried some of their dead, and obtained supplies and water. Colonization;Spain of the Americas

The fleet’s next destination was Santo Domingo on the southern side of Hispaniola Hispaniola . They arrived there on December 31, 1585. Many citizens had fled with their valuables, and the Spanish had made ill-planned attempts to prepare defenses. Following his accustomed tactic of assaulting a settlement, Drake landed Carleill and about one thousand men at night a short distance from the city and prepared the fleet to fire on the city in support of the land attack. On January 1, 1586, Drake launched his two-pronged attack, and by midday he had overcome Spanish resistance. Drake’s demands for a ransom to spare the city were rebuffed, and his men began plundering the town, taking money, brass cannon, and church bells. To apply pressure on the Spanish to grant his ransom request, Drake ordered the burning of portions of the settlement, which caused the Spanish to agree to pay 25,000 ducats by January 30, 1586. Before leaving, Drake exchanged three of his older vessels for three newer Spanish ships and also requisitioned a Spanish ship, which he renamed New Year’s Gift.

The assault was a substantial psychological and financial blow to Philip II, exposing the defenseless state of Spanish colonies and causing the reassignment of resources designated for use in Europe to the Caribbean and the Americas.

After leaving Santo Domingo, the fleet sailed for Cartagena, along the northern coast of South America. Spurred by warnings received from Santo Domingo, local officials had taken precautions—women, children, and valuables were removed from the city; barricades were erected; trenches were dug; a huge chain was stretched across the harbor; and galleys were positioned in the harbor. On February 9, 1586, Drake tauntingly sailed his fleet in front of the city and into the outer harbor. Repeating the tactics successful at Santo Domingo—a night landing of troops and a ground assault supported by fire from his fleet—Drake was in control of the city by morning, as gaps in the defenses and the poor morale of the defenders contributed to the city’s swift collapse. Drake’s exorbitant ransom demand of 500,000 gold ducats was rejected by the Spanish, who offered 25,000 gold ducats instead.

Negotiations became protracted when Drake insulted the Spanish officials after he discovered a letter in which Philip II had called Drake a pirate. As he had done at Santo Domingo, Drake burned parts of the city to force compliance with his ransom demands; the Spanish agreed to pay 110,000 ducats, beginning March 10, 1586. The king’s bullion was used for the ransom, and wealthy individuals and Franciscan friars paid separate ransoms. In addition to this loot, Drake’s men removed brass cannon from the town and galleys and plundered valuables from individuals and churches in the city. Disputes developed among the English over the accounting of ransom and plunder, and many of the crew openly expressed a desire to return to England.

The fleet left for Cuba on March 31, 1586, but returned to Cartagena several days later to repair a badly leaking ship, redistribute plunder and cargo between ships, and bake biscuits in preparation for the return voyage to England. On April 14, 1586, the fleet resumed its journey to Cuba. The Havana settlement was not attacked because of its strong fortifications, so Drake sailed for Florida, arriving at St. Augustine St. Augustine[Saint Augustine];English raid of on May 27, 1586. In an attack launched the following day, Drake destroyed the fort and burned the settlement and crops. The plunder of the town yielded food, cannon, and a treasure chest containing 6,000 ducats. Santa Elena, a settlement north of St. Augustine, was spared attack because of dangerous shoals.

The last stop for the fleet was Sir Walter Ralegh’s Roanoke Colony Roanoke, lost colony of in June, along the Outer Banks of what is now North Carolina. Governor Ralph Lane revealed the serious state of the colonists because hoped-for supplies had not arrived. Generously, Drake offered supplies and one ship to transport the colonists to England, but these plans changed because a storm of three days’ duration dispersed Drake’s fleet and the ship promised the colonists had sailed for England. Modifying his original offer, Drake transported the 105 colonists to England, arriving at Portsmouth on July 27, 1586, just five days after the ship that had left earlier during the storm. Colonization;England of Virginia


The hoped-for financial gain did not materialize because the booty did not cover the £40,000 investment in the expedition. Also, the sailors and soldiers had to wait for their pay. On another level, however, the expedition had been a tremendous success; English and European Protestants were exultant over the damage inflicted on Catholic Spain’s pride and resources, and Drake would be sent in 1587 to raid Cádiz to disrupt preparations for the Spanish Armada. Anglo-Spanish War (1587-c. 1600)[Anglo Spanish War (1587-c. 1600)]

The voyage also expanded English knowledge of the Americas and helped stimulate interest in further colonization. Philip II was forced to expend greater resources to defend Spanish settlements in the Americas, which diverted funds that had been earmarked for the Spanish Armada against England and for stopping the Dutch Wars of Independence.

Further Reading
  • citation-type="booksimple"

    xlink:type="simple">Dudley, Wade G. Drake: For God, Queen, and Plunder. Washington, D.C.: Brassey’, 2003. Monograph on Drake’s naval exploits that paints a picture of Elizabethan privateering and the naval battles between England and Spain in Drake’s time.
  • citation-type="booksimple"

    xlink:type="simple">Keeler, Mary Frear, ed. Sir Francis Drake’s West Indian Voyage, 1585-86. London: Hakluyt Society, 1981. An extensive edition of primary documents with an introduction, analysis, and a glossary of the major personnel.
  • citation-type="booksimple"

    xlink:type="simple">Kelsey, Harry. Sir Francis Drake: The Queen’s Pirate. New Haven, Conn.: Yale University Press, 1998. An excellent scholarly analysis of Drake’s career, based on archival research and supported by excellent maps.
  • citation-type="booksimple"

    xlink:type="simple">Parker, Geoffrey. The Grand Strategy of Philip II. New Haven, Conn.: Yale University Press, 1996. This study puts Drake’s voyage within the context of the Anglo-Spanish conflict by analyzing Philip’s response to the English actions.
  • citation-type="booksimple"

    xlink:type="simple">Sugden, John. Sir Francis Drake. New York: Touchstone Books, 1992. A readable scholarly biography with several chapters on the voyage.

1495-1510: West Indian Uprisings

1500-1530’s: Portugal Begins to Colonize Brazil

1558-1603: Reign of Elizabeth I

June 17, 1579: Drake Lands in Northern California

July 4, 1584-1590: Lost Colony of Roanoke

July 31-Aug. 8, 1588: Defeat of the Spanish Armada

Categories: History