[6] On 15 December 1577 the English privateer Francis Drake set sail from Plymouth to raid Spanish treasure ships and settlements in the Americas.
[8] 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.
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.
[9] 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.
After getting permission for his proposed raids Cavendish built a larger 120 ton sailing ship, with eighteen guns, named the Desire.
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.
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.
[18] 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.
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.
[20] 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 Valparaiso a place which they intended to stop at.
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.
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.
[26] 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.
The English imprisoned the Spanish lookout and then destroyed two ships of 200 tons each, which were being built by Antonio del Castillo and Juan Toscano and were about to be launched.
Moving up to the coast Cavendish weighed anchor at Tenacatitia Bay and took thirty men inland to the village of Acatlan where they burned most of the houses and defaced the church.
[34] After leaving Chacala on 20 September 1587 Cavendish then sailed past Compostela and anchored in one of the islands of Tres Marias staying for five days where some iguanas and birds were caught.
After several hours of battle during which Cavendish used his cannon to fire ball and grape shot into the galleon while the Spanish tried to fight back with small arms.
[40] With the great disparity in size, the Content and Desire had to pick and choose what rich cargo they wanted to transfer to their ships from the much larger Santa Ana.
[41] In addition a Portuguese traveller Nicholas Roderigo familiar with China and the pilot Alonso de Valladolid both defected and were willing to work with the English.
[16] The prisoners helped load all the gold (about 100 troy pounds or 122,000 pesos' worth) and the English picked through the silks, damasks, musks (used in perfume manufacture), spices, wines and the ship's supplies for what they could carry.
The ship's guns were discharged and there was display of fireworks – the culmination was the Santa Ana being set on fire and left adrift burning.
Touching at northeastern Samar on 14 January 1588, Desire passed through the narrow San Bernardino Strait into the Sibuyan Sea, then sailed south to Panay.
Desire anchored off the island of Capul where Cavendish spent several days with a native chief who traded them with vegetables, hens and hogs for linen and captured Spanish specie.
An attempt to make a surprise attack on a galleon under construction at Areval shipyard ended in failure when the landing party was discovered early on; they promptly returned to Desire without loss.
Four days later through the mist they came across False Bay off Southern Africa where they watered and gathered fruit (Cavendish mistook this for the Cape of Good Hope).
[53] About the end of August they passed the Azores and on 3 September 1588 met a Flemish hulk from Lisbon which informed them of the defeat of the Spanish Armada, much to the Englishmen's great rejoicing.
The Desire was only the third ship to circumnavigate the globe after the Victoria of Ferdinand Magellan (journey completed by Juan Sebastián Elcano) and the Golden Hind of Francis Drake.
Cavendish and Drake's reconnaissance work in the East Indies had laid the foundation for further privateering to even more distant zones of conflict.
[56] Bishop Salazar in the Philippines bitterly complained in a letter to King Philip II that an English youth at about 22 years, with a wretched little vessel of about 100 tuns, 40 to 50 companions boasted of the damage he had wrought, and went away laughing.
[61][62] The Dutch were next to attempt Drake's and Cavendish's feat – Simon de Cordes and Oliver Van Noort completed their raids of circumnavigation against the Spanish.