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Circumnavigation (1577–1580)

Following the success of the Panama isthmus raid, Drake's so-called "Famous Voyage" – an expedition against the Spanish along the Pacific coast of the Americas – was organized and financed by a private syndicate that included Francis Walsingham, Robert Dudley, 1st Earl of Leicester, John Hawkins, Christopher Hatton, and Drake himself. Drake acted on the plan authored by Sir Richard Grenville, who in 1574 had received a royal patent for that purpose; just a year later this patent had been rescinded after Elizabeth I learned of Grenville's intentions against the Spanish. Elizabeth likely invested in Drake's voyage to South America in 1577, but never issued him a formal commission. This would be the first circumnavigation in 58 years.

Diego was once again employed under Drake; his fluency in Spanish and English would make him a useful interpreter when Spaniards or Spanish-speaking Portuguese were captured. He was employed as Drake's servant and was paid wages like the rest of the crew. Drake and the fleet set out from Plymouth on 15 November 1577, but bad weather threatened him and his fleet. They were forced to take refuge in Falmouth, Cornwall, from where they returned to Plymouth for repair.

After this major setback, Drake set sail again on 13 December aboard Pelican with four other ships and 164 men. He soon added a sixth ship, Mary (formerly Santa María), a Portuguese merchant ship that had been captured off the coast of Africa near the Cape Verde Islands. He also kidnapped its captain, Nuno da Silva, a man with considerable experience navigating in South American waters.

Drake's fleet suffered great attrition; he scuttled both Christopher and the flyboat Swan due to loss of men on the Atlantic crossing. He made landfall at the gloomy bay of Puerto San Julián, in what is now Argentina. Ferdinand Magellan had called there half a century earlier, where he put to death some mutineers. Drake's men saw weathered and bleached skeletons on the Spanish gibbets. Following Magellan's example, Drake tried and executed his own "mutineer" Thomas Doughty. The crew discovered that Mary had rotting timbers, so they put the vessel ashore, stripped it, and abandoned it. Drake decided to remain the winter in San Julián before attempting the Strait of Magellan.