Battle of San Juan (1595)

The Battle of San Juan (1595) was a Spanish victory during the Anglo–Spanish War. This war broke out in 1585 and was fought not only in the European theatre but in Spain's American colonies. After emerging from six years of disgrace following the resounding defeat of the English Armada at Lisbon in 1589, Francis Drake embarked on a long and disastrous campaign against Hispanic America, suffering several consecutive defeats there. On 22 November 1595 Drake and John Hawkins tried to invade San Juan with 27 ships and 2,500 men. After failing to be able to land at the Ensenada del Escambron on the eastern end of San Juan Islet, he attempted to sail into San Juan Bay with the intention of sacking the city.[5] Unable to capture the island, following the death of his comrade, John Hawkins, Drake abandoned San Juan, and set sail for Panama where he died from disease and received a burial at sea after failing to establish an English settlement in America.

Battle of San Juan (1595)
Part of the Anglo-Spanish War (1585)

Ship entering the bay of San Juan, in front of Fort San Felipe del Morro - view from Isla de Cabras.
Date22 November 1595
Result Spanish victory
Spain Spain Kingdom of England England
Commanders and leaders
Admiral Pedro Tello de Guzman
Admiral Gonzalo Méndez de Cancio
Capt. Sancho Pardo Donlebún
Governor Pedro Suárez Coronel[1][2][3]
Francis Drake
John Hawkins
5 frigates,
700 soldiers and 800 sailors,
70 land-based guns[4][2][1]
27 ships,
2,500 soldiers and sailors
Casualties and losses
1 frigate burnt,
40 killed[4]
8–10 boats sunk,
400 killed[4]


Queen Elizabeth I of England sent Sir Francis Drake and Sir John Hawkins on an expedition against the Spanish stronghold of Puerto Rico and Panama, in an attempt to strike a blow against the source of Spain's gold and silver. They set sail from Plymouth on 28 Aug. 1595, with a fleet of 27 ships and 2,500 men. Previous to that, the Spanish West Indian Fleet under the command of Gen. Sancho Pardo Osorio had sailed from Havana on 10 March with 2,000,000 pesos in gold and silver, bound for Spain. Damage from a storm in the Bermuda Channel on the 15th, necessitated a trip to Puerto Rico for repairs, which was reached on 9 April. The treasure cargo was placed in La Fortaleza for safekeeping while repairs were undertaken. Admiral Pedro Tello de Guzmán, commanding 5 frigates, was sent to retrieve the treasure. Along the way to Puerto Rico, Tello captured one of Drake's ships, the Francis, near Guadeloupe, upon which he learned of Drake's mission, and hastened to Puerto Rico ahead of Drake.[3][1][2]


General Sancho took command of the shore defenses, Admiral Gonzalo Mendez de Cauzo commanded the forts, while Tello defended the harbor with his frigates. The Spanish decided to sink two vessels at the harbor entrance, with Tello's frigates just behind, to prevent the English from entering the harbor. The Spanish defense consisted of 1500 men, 800 of whom manned the 5 frigates, with 70 land-based cannon in addition to those on the frigates. Hawkins had died on 12 Nov. from a fever, while Drake arrived offshore Puerto Rico on 22 Nov., anchoring off the Boquerón Inlet. The Spanish brought up artillery and scored hits upon Drake's ship, Defiance, killing Sir Nicholas Clifford and Browne. Drake moved his fleet to the vicinity of Isla de Cabras on 23 Nov.[2][1][3]

According to a Spanish account,[2]

The same Thursday, 23rd, San Clement's Day, at ten o'clock at night, when it was quite dark, the enemy commenced an attack on the port with twenty-five boats, each carrying fifty or sixty men well armed, with the view of burning the frigates, as was afterwards seen, and they all entered up close to the platform of the Rock (battery), ranging themselves under the fire of the artillery...Most of the boats attacked the Capitana, the Texeda frigate, setting fire to her at the bow, and throwing into her a quantity of fire-pots and shells while ours succeeded in extinguishing the flames before they had done any damage, the fight being carried on by cannon, musquetry and stones.

"At the same time they set fire to the Sta. Ysabel and Magdalena frigates, and to the Sancta Clara, which was extinguished; but the third time that the Magdalena frigate, of which Domingo de Ynsaurraga was captain, took fire, it was impossible to extinguish the flames, as the ship took fire at the stern and burned furiously; and all that could be done to maintain a footing on board, was done by the aforesaid captain and the people with him, until the ship was just burnt down and twelve men were killed by the enemy's musquetry, besides as many more burnt...The battle lasted for an hour, the most obstinately contested that was ever seen, and the whole port was illumined by the burning frigate in a manner favourable for the rest, who could thus see to point our artillery and that of the forts, with which, and with the musquetry and stones thrown frown the frigate, they did such effect, that the enemy, after about an hour, during which the combat lasted, as I have said, retreated with the loss of nine or ten boats and more than four hundred men, besides many more wounded; while on our side, the only loss was that of the frigate and forty men killed or burnt, besides a few wounded by the musquetry.

On 25 Nov., Drake's fleet gave up the fight and departed.[2][1][3]


The Spanish treasure fleet finally left Puerto Rico on 20 Dec. 1595, bound for Spain.[2]

This defeat and the defeat at Pinos ended English hopes of establishing a presence in the Caribbean Sea. In the first days of 1596 Drake was diagnosed with dysentery, and on 28 January he would die.

Popular Culture

The battle is mentioned in Lope de Vega's epic poem La Dragontea[6]


  1. ^ a b c d e The Forts of Old San Juan. Washington, D.C.: Division of Publications, National Park Service, U.S. Dept. of the Interior. 2018. pp. 31–34. ISBN 9780912627625.
  2. ^ a b c d e f g Maynarde, Thomas (2016). Cooley, W.A. (ed.). Sir Francis Drake, His Voyage, 1595, including An Account Of What Took Place At San Juan De Puerto Rico, In The Indies, With The English Fleet Under The Command OF Francis Drake and John Hawkins, On The 23rd November 1595 (The Hayluyt Society ed.). New York: Routledge. p. 4-5,9-11,46-63. ISBN 9781409412700. Retrieved 8 March 2019.
  3. ^ a b c d Van Middeldyk, R.A. (1903). Brumbaugh, Martin (ed.). The History of Puerto Rico: From the Spanish Discovery to the American Occupation. D. Appleton and Company. pp. 114–119. Retrieved 6 March 2019.
  4. ^ a b c Van Middeldyk p. 68
  5. ^ The Life of Sir Francis Drake
  6. ^ Dislates y Disparates sobre el Relámpago del Catatumbo: La expedición de Drake, de 1595, Ángel Vicente Muñoz García, Centro de Modelado Científico, Maracaibo, agosto 2016.

Additional Reading

  • Konstam, Angus (2008). Piracy: the complete history. Oxford, UK: Osprey Publishing. ISBN 978-1-84603-240-0.
  • Van Middeldyk, R. A. (2008). The History of Puerto Rico. Teddington, UK: Echo Library. ISBN 978-1-4068-7497-6.
Battle of Cartagena de Indias (1586)

The Battle of Cartagena de Indias (1586) or the Capture of Cartagena de Indias was a military and naval action fought on 9–11 February 1586, of the recently declared Anglo-Spanish War that resulted in the assault and capture by English soldiers and sailors of the Spanish city of Cartagena de Indias governed by Pedro de Bustos on the Spanish Main. The English were led by Francis Drake. The raid was part of his Great Expedition to the Spanish New World. The English soldiers then occupied the city for over two months and captured much booty along with a ransom before departing on 12 April.

Battle of Guadalupe Island (1595)

The Battle of Guadalupe Island, also known as the Battle of Guadalupe, was a naval action that took place off Guadalupe Island (French: Guadeloupe), Caribbean Sea, on 8 November 1595, between a Spanish force of five frigates commanded by Don Pedro Tello de Guzmán and Don Gonzalo Méndez de Cancio (who was appointed Admiral on 19 August 1595), and an English squadron of nine ships (rear of Francis Drake's fleet), during the unsuccessful English military expedition of 1595 against Spain and their possessions, led by Sir Francis Drake himself, Sir John Hawkins and Sir Thomas Baskerville, as the context of the Anglo-Spanish War (1585–1604). The result was a Spanish victory. One of the English ships, the Francis, was captured and the others fled from the battle. Then, knowing Drake's plans, the Spanish flotilla took advantage over the bulk of Drake's fleet, and arrived at San Juan on 13 November, reinforcing the town with 500 soldiers and supplies. The Spaniards organized different artillery positions in strategic locations, and the five frigates were positioned to cover the entrance of the bay with their artillery, awaiting the arrival of Drake. On 22 November, with the defenses completed, the English fleet arrived off San Juan and tried to invade the town. The result was another Spanish victory over Drake's forces.

Battle of San Juan

Battle of San Juan may refer to:

Battle of San Juan (1595), an English attack on San Juan, Puerto Rico

Battle of San Juan (1598), an English attack on San Juan, Puerto Rico

Battle of San Juan (1625), a Dutch attack on San Juan, Puerto Rico

Battle of San Juan (1797), a British attack on San Juan, Puerto Rico

Battle of San Juan and Chorrillos, an 1881 battle between Chile and Peru

Battle of San Juan del Monte, an 1896 attack on a Spanish magazine in San Juan del Monte, Manila, Philippines

First Battle of San Juan (1898) or Bombardment of San Juan, a naval bombardment initiated by an American fleet against the Spanish fortifications of San Juan, Puerto Rico

Second Battle of San Juan (1898), a naval engagement off San Juan, Puerto Rico

Third Battle of San Juan (1898), a Spanish sortie to rescue a blockade runner off San Juan, Puerto Rico

Battle of Santo Domingo (1586)

The Battle of Santo Domingo (1586) or the Capture of Santo Domingo was a military and naval action fought on 1 January 1586, of the recently declared Anglo-Spanish War that resulted in the assault and capture by English soldiers and sailors of the Spanish city of Santo Domingo governed by Cristóbal de Ovalle on the Spanish island of Hispaniola. The English were led by Francis Drake and was part of his Great Expedition to the raid the Spanish New World in a kind of preemptive strike. The English soldiers then occupied the city for over a month and captured much booty along with a 25,000 ducat ransom before departing on 1 February.

Castillo San Felipe del Morro

Castillo San Felipe del Morro also known as Fuerte San Felipe del Morro or Castillo del Morro, is a 16th-century citadel located in San Juan, Puerto Rico.

Gonzalo Méndez de Canço

Gonzalo Méndez de Canço (or "de Cancio", or "de Cauzo") y Donlebún (c. 1554 – March 31, 1622) was a Spanish admiral who served as the seventh governor of the Spanish province of La Florida (1596-1603). He fought in the Battle of San Juan (1595) against the English admiral Francis Drake. During his tenure as governor of Florida, he dealt severely with a rebellion known as Juanillo´s revolt among the Native Americans in Guale, forcing them, as well as other tribes in Florida, to submit to Spanish domination. De Canço was best known, however, for promoting the cultivation of maize in the province, and for introducing its cultivation to Asturias, Spain, where it eventually became an important crop.

Miguel Enríquez (privateer)

D. Miguel Enríquez (c. 1674–1743), was a privateer from San Juan, Puerto Rico who operated during the early 18th century. A mulatto born out of wedlock, Enríquez was a shoemaker by occupation. After working for the governor as a salesman he was recruited to defend Puerto Rico, then a colony of the Spanish Empire, and commanded a small fleet that intercepted foreign merchant ships and other vessels dedicated to contraband. These outlaws were thriving in the waters of the Caribbean Sea and the Atlantic Ocean, notably in the areas surrounding Saint Thomas, Curaçao and Jamaica. Operating during the height of the Golden Age of Piracy, his fleet was also credited with controlling the proliferation of buccaneers in the region. However, he was considered a pirate himself by the enemies of Spain, since it was common practice of the government to ignore when foreign ships were attacked. After some time operating independently, Enríquez received a letter of marque and reprisal from the Spanish Crown, this was a special permit granting him the privileges of a privateer. Corsairs from Puerto Rico were often called guardacostas, or "coast guards." They operated in the same fashion as any other pirate, the only difference was that they did it in the name of Spain, protecting imperial trade restrictions. Employing a systematic approach, Enríquez was able to become the most successful and influential Puerto Rican of his time. However, despite this, he was never able to gain the acceptance of the higher social classes, something that he strived to earn throughout his life.

During his years as a privateer, Enríquez established close links with the Spanish Monarchy. His ships were also responsible for the distribution of urgent messages that arrived at San Juan or La Aguada to the rest of the West Indies. When there was a shortage of royal vessels, Enríquez's fleet was responsible for transporting items on behalf of Spain without charge. His fleet also provided transportation for the authorities that arrived at Puerto Rico en route to other locations and for missionaries. Throughout the War of the Spanish Succession, Enríquez's fleet was responsible for guarding the Antilles from incursions by the British and Dutch. Among the places where he established connections was the adjacent island of St. Thomas. Enríquez also dealt directly with the governor of Curaçao. At a time when letters of marque were being regularly issued in neighboring islands his actions converted San Juan into one of the most important ports in the Caribbean. Between 1702 and 1713 Enríquez owned a fleet of more than thirty vessels, losing at least a dozen and capturing more than twenty others. By the time that his career was over, he had reportedly commanded a fleet of over 300 privateer ships, of which approximately 150 were lost, employing close to 1,500 sailors.In 1717, Great Britain occupied the island of Vieques which was under the control of the Spanish Government of Puerto Rico. According to the British government, they did not recognize the Spanish claim to the island which they referred to as "Crab Island". Enríquez, with the consent of the government, organized an expeditionary force which consisted of two ships with seven members of the regular Spanish Army and 286 members of the Puerto Rican militia. The ships were escorted by a Spanish warship under the command of Naval Commander José Rocher. Enríquez's men fought and defeated the British in Vieques, taking most of their enemy to the mainland of Puerto Rico as their prisoners. He was received as a national hero when he returned the island of Vieques to the Spanish Empire and to the governorship of Puerto Rico. The British government became alarmed and sent a warship to San Juan. Further confrontation between both nations was avoided when the Spanish authorities returned the prisoners. His fleet also participated in other military expeditions in 1728 and 1729.

Enríquez received several recognitions and exemptions that facilitated his work and contributed towards his vast wealth. Under the order of King Philip V (1683–1746), he was awarded The Gold Medal of the Royal Effigy (Spanish: "Medalla de oro de la Real Efigie") in 1713 and was named Capitán de Mar y Guerra y Armador de Corsos (loosely translated as Captain of the Seas and War and Chief Provider to the Crown Corsairs). The Crown also granted him a Royal Auxiliary Identification Document (Spanish: Real Cédula Auxiliar), which allowed him to directly seek help from the Council of the Indies regardless of how insignificant a conflict was.

Enríquez also acquired the local rights of the Guinea Company and the Royal Asiento of Great Britain, organizations dedicated to slave trading which were authorized to do so by Spain. His actions placed him at odds with several influential members of San Juan's society. To counter this, Enríquez supported any new governor by offering his services and providing other help. However, all but José Antonio Mendizábal unsuccessfully tried to revoke his privateering contract, often finding themselves in trouble when he responded by using his resources. The most notable example was Juan de Ribera, who Enríquez managed to remove from the office of governor after an arduous conflict by employing his influence. He also pursued the favor of the bishops appointed to San Juan, earning the support of Pedro de la Concepción Urtiaga and Fernando de Valbidia, but failing to earn the trust of Lorenzo Pizarro. Enríquez's influence extended to several other systems, including the courts and military. He owned 300 slaves and his fortune, at the time, was among the largest in the Americas. Throughout his career, Enríquez was persecuted by the Spanish elite in the island and jailed on various occasions. At the peak of his success, he was able to employ his influence to have governor Danío Granados prosecuted and jailed. However, as international politics evolved, his influence dwindled. By the time that Matías de Abadía became governor, Enríquez was unable to accomplish his removal from office. He was charged with smuggling and stripped of all his power and wealth by the government. Enríquez fled and took refuge in the Catholic Church, which he regularly attended. By being generous with his donations to the bishopric, he had gained allies who would protect him throughout the years. The charges of smuggling made by the Spanish government were eventually dropped, but Enríquez chose to remain in the convent where he died a pauper.

San Juan Bay

San Juan Bay (Spanish: Bahía de San Juan) is the inlet adjacent to Old San Juan in northeastern Puerto Rico. It is about 3.5 miles (5.6 km) in length, the largest body of water in an estuary of about 97 square miles (250 km2) of channels, inlets and eight interconnected lagoons. The San Juan bay is home to the island's busiest harbor and its history dates back to at least 1508.

Sancho Pardo Donlebún

Sancho Pardo Donlebún, also called Sancho Pardo Osorio, (Donlebún, near Castropol, Asturias, Spain, circa 1537 - drowned in the Atlantic Ocean, near Lisbon, October, 1607), was a notorious seafarer.

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