Thomas Cavendish's circumnavigation was a voyage of raid and exploration by English navigator and sailor Thomas Cavendish which took place during the Anglo–Spanish War between 21 July 1586 and 9 September 1588. Following in the footsteps of Francis Drake who circumnavigated the globe, Thomas Cavendish was influenced in an attempt to repeat the feat. As such it was the first deliberately planned voyage of the globe.

Having set out with his three ships, the English raided three Spanish settlements and captured or burned thirteen ships. Among these was a rich 600 ton sailing ship, a Manila Galleon called Santa Ana (also called Santa Anna); the biggest treasure haul that ever fell into English hands. With only one ship left, Cavendish returned to England on 9 September 1588 completing a full circumnavigation of the Earth in record time. The voyage itself was hugely successful and made Cavendish rich from captured Spanish gold, silk and treasure from the Pacific and the Spanish Philippines. Cavendish was subsequently knighted by Queen Elizabeth I of England.

Background On 15 December 1577 the English privateer Francis Drake set sail from Plymouth to raid Spanish treasure ships and settlements in the Americas. Drake had investors in the voyage in the hope that they could make a profit from the plunder that the English would capture. After nearly three years at sea Drake in the Golden Hinde returned to England in 26 September 1580 and had accomplished the feat of circumnavigating the globe. The investors had made huge profits from the voyage, and there was a desire to launch more expeditions in the same manner. Drake was subsequently knighted by Queen Elizabeth I. After Drake's voyage, the Spanish felt vulnerable in their colonies and so began to better prepare their settlements against attack by the English, which they knew that they would attack again. Francisco de Toledo began to build a series of fortifications on the coast of the southern tip of South America and established 'la Armada del Mar del Sur' (the Southern Fleet) in the port of El Callao.

With Drake's attacks and English involvement in the Dutch Revolt this increased the annoyance of King Philip II of Spain, and Anglo-Spanish relations continued to deteriorate, eventually moving towards open war. After the execution of Mary Queen of Scots, a Catholic rival to Elizabeth's throne, the inevitable war began in 1585.

Thomas Cavendish meanwhile, a commoner, had inherited his father's wealth aged twelve, and had used some of this money to purchase the ship Elizabeth. He had joined the expedition fleet of Sir Richard Grenville on his journey to Virginia in 1585 and in the process capturing a 400-ton Spanish galleon Santa Maria de San Vicente. Cavendish with the experience he gained was determined to follow Drake by raiding Spanish colonial ports and ships, and also attempt to circumnavigate the globe. He planned his own voyage, mortgaging all his lands and raising upwards of some £10,000. After getting permission for his proposed raids Cavendish built a larger 120 ton sailing ship, with eighteen guns, named the Desire. He was joined by the sixty ton, ten gun ship Content, and the forty ton supply ship Hugh Gallant. In total the complement of the expedition was 123 men and boys, some of whom had been with Drake on his voyage around the world. Taking part in the voyage were Francis Pretty a Suffolk gentleman, sailor and diarist, the mathematician and geographer Robert Hues with "purposely for taking the true Latitude of places";MS Rawl. B 158, Bodleian Library, Oxford. and the merchant Thomas Eldred. The complement also included workmen who brought with them tools, a portable forge and large quantities of salt to preserve food along the way.

Voyage On 21 July 1586 Cavendish left Plymouth Sound with the three ships. Five days later, off Cape Finisterre they were involved in a minor skirmish with five Biscayne ships at long range for nearly three hours that only ended when darkness set in and contact was lost. Sailing past the Canary Islands they reached the West African coast (present day Sierra Leone) on 21 August. Eleven days were spent there procuring provisions and water. Whilst there they met the locals and even joined in with dances and festivities in the night. Cavendish intended to capture a Portuguese ship but due to a miscommunication with the natives they in turn burned the native village instead, carrying off with what little loot they could find. The natives retaliated by shooting poisoned arrows, one of which hit an English sailor who died before they sailed off.

Across to South America

In early September Cavendish departed the shores of Africa and began to cross the Atlantic for Portuguese Brazil. After watering in the Cape Verde Islands, on November 1, 1586, the English reached one of the many islands off São Sebastião, there he took on water and built a pinnace before heading further South four days later.

By mid December Cavendish sailed further down the South American East coast and came into an estuary and a suitable harbour. He named this as Port Desire, after his flagship, and met only a few Native Americans, who shot arrows that wounded some of the crew. Having found little fresh water Cavendish sailed on and soon reached the Strait of Magellan on 6 January 1587 where they soon encountered heavy swells from a storm.

Strait of Magellan

Entering the Strait of Magellan, Cavendish's three vessels passed the Segunda Angostura, the narrowest points of the Straits. The English anchored first at the island of Santa Magdalena. There, in two hours, they killed and salted two barrels-full of penguins for food. Following this they reached Pedro Sarmiento de Gamboa's now ruined settlement of Rey don Felipe by 19 January 1587. Incredibly there were twelve men and three women out of the original 400 Spanish settlers. Cavendish cruelly refused them any assistance except for Tomé Hernandez a veteran pilot that Cavendish intended to make use of. He removed six cannons and then renamed the place 'Port Famine'.

Cavendish sailed in the second half of the Strait and then managed extensive exploration of the many inlets, labyrinths, intricate channels of the islands and broken lands of Tierra del Fuego and its environs. On 24 February 1587 they emerged from the strait into the Pacific and sailed up the western coast South America.

Raids on Spanish American West Coast Cavendish however soon ran into a storm – this pushed the ships further north, the Hugh Gallant was then separated from the other two ships. The storm lasted for nearly four days making it impossible for the men to sleep. They finally reached Santa María Island on 15 March 1587. Having landing a party of 70 men the Englishmen were greeted with kindness by the Natives, who supplied them with food, and who received in return entertainment in the captain's ship. The English then traded supplies with the natives, who had valuable captured Spanish goods. Days later the Hugh Gallant appeared and reunited with the others between Santa Maria Island and the mainland.

Concepción, Arica and Paita The Englishmen steered north toward Mocha Island, which they sighted on 24 March 1587 – by the end of the month they had arrived at Quintero, having overshot Valparaíso, a place which they intended to stop at. They anchored just off Concepción; here they had an encounter with Spaniards on horseback, but they only watched the English from a distance. Cavendish travelled some eight miles inland, declaring the valley area to be 'very fruitful'. Tomé Hernandez was sent to parley with the local population but this turned out to be a betrayal as he instead made his escape. He warned the local Spanish inhabitants, who grouped together numbering nearly 200 then launched an ambush on the English whilst they were collecting water. The Spanish were eventually driven off with the loss of twenty four men, but not before the English had lost seven men killed and nine captured. Cavendish however stayed in Quintero Bay before leaving 5 April heading towards the port of Arica and entering the tropic zone.

Before reaching Arica, Cavendish on 23 April 1587 came across a barque loaded with wine, and captured the vessel. It was renamed George given the proximity date of Saint George's Day. George was subsequently incorporated into the squadron. The following morning a large Spanish ship and four barks were captured off Arica. Arriving at Arica Cavendish saw the town ready for its defence and even exchanged shot with the Spanish shore batteries. A design of landing and storming the town was abandoned but another three ships were burned in the harbour before the English sailed northwest two days later. Cargo included barrels of Chilean wine and various dispatches and a Greek pilot Jorge Carandino of Chios. Cavendish resorted to torture in order to oblige prisoners to disclose the contents of letter that they had thrown overboard.

On 14 May 1587 Cavendish reached Pisco and intercepted two Spanish merchantmen three days later, which he pillaged and burned. Using the port as a base to re-victual the English ships then dispersed to carry out independent actions of their own – two days later the Hugh Gallant captured a vessel of 300 tons bringing in timber from Guayaquil but abandoned her to sink because she was taking on water. The Hugh Gallant then descended upon Paita four days later having a captured a bark in the harbour. Sixty men from the ship waded ashore to occupy the town while its 300 inhabitants fled inland. Threatened with a ransom the citizens refused to raise any, so the English set the dwellings ablaze before sailing north robbing the inhabitants of some twenty five pounds in sliver pesos.

Puna Island and Huatulco With the ships reunited they all dropped anchor off Puná Island on 25 May 1587. Cavendish intended to careen and repair the ships. The crew noted the idyllic nature of the island with plenty of fruit. When they landed however about sixteen of Cavendish's men were surprised by a large group Spaniards and Indians having come from Quito. Under Captain Juan de Galarza, they initially scattered the English and more skirmishes followed. The English however gained the upper hand when Cavendish landed with more men and drove off the Spanish killing some 46 or a loss of nine sailors killed and three more captured. Cavendish then ordered all of Puná's buildings, ships and crops burned. Some 300 buildings were set on fire, a ship of 250 tons was burnt at anchor whilst four more on the stocks were looted and then burnt; the church was also burnt and its bells carried away. The English stayed making sure everything of value was taken before sailing on.

Whilst in an inlet near Guayaquil on 5 June 1587, a decision was made to abandon the Hugh Gallant and the George due to lack of men to crew both and that repairs would take longer. They stripped both vessels of iron, canvas and anything useful before setting both alight, and departed eleven days later. The held a northerly course for over month before sighting New Spain.

News of the raids reached Panama by early July, and two ships were sent out to intercept the English raiders but they were two weeks late. In addition news reached Álvaro Manrique de Zúñiga the Viceroy of New Spain but again did not reach him in time so was unable to commit to any orders.

On 9 July 1587 Cavendish captured a vessel – although it was without cargo one of the captured pilots Michael Sancius revealed that a Manila galleon was expected in October or November 1587 and usually stopped at Cabo San Lucas on the Baja California peninsula before going on to Acapulco.More evidence of this emerged when soon after another vessel was taken which was supposed to have warned the galleon of impending English raiders.