Thomas Cavendish began a planned privateering voyage intended to circle the globe, sailing with Desire, Content, and Hugh Gallant. The expedition took place during the wider Anglo-Spanish War and aimed to raid Spanish shipping and settlements while demonstrating English reach at sea.
After passing the Canary Islands, Cavendish’s ships stopped on the West African coast near present-day Sierra Leone to take on fresh water and provisions. This kind of resupply stop was crucial before a long Atlantic crossing with limited storage and spoilage risks.
Cavendish reached the estuary he called Port Desire (today Puerto Deseado, Argentina), naming it after his flagship Desire. The stop shows how English privateers combined raiding goals with navigation and place-naming along strategic coastlines.
The expedition reached the Strait of Magellan, the key passage from the Atlantic to the Pacific for ships sailing around South America. Getting through the strait was a major turning point, because it opened access to Spain’s Pacific coast routes and ports.
After weeks of difficult sailing through the strait, Cavendish’s ships entered the Pacific. From this point, the voyage shifted from survival-focused navigation to active privateering against Spanish shipping along the Pacific coast of South America.
Cavendish burned Hugh Gallant, reducing his fleet as manpower and ship condition became limiting factors. Losing a ship narrowed his options but also concentrated his crew and supplies onto fewer vessels for the next phase of raiding.
Cavendish attacked and looted the Spanish port of Huatulco (in present-day Oaxaca, Mexico) and burned structures and shipping before moving on. Raids like this were meant to disrupt Spanish supply networks and gather intelligence on richer targets.
Off Cabo San Lucas, Cavendish seized the Manila galleon Santa Ana, a major prize on the Pacific trade route linking the Philippines and New Spain. The capture delivered valuable cargo and became the financial high point of the voyage, strengthening English privateering ambitions in the Pacific.
Soon after the capture of Santa Ana, Content separated from Desire and was never seen again. The loss left Cavendish with a single ship for the rest of the circumnavigation, raising the risks of shipwreck, shortage, and capture.
Cavendish’s ship Desire arrived at Guam (then often called part of the “Ladrones” islands in English sources) and traded for fresh supplies. This stop helped restore food and water stocks after the long Pacific crossing, supporting the westward continuation of the voyage.
After taking on supplies and gathering information in island ports, Cavendish left Java and began the homeward leg across the Indian Ocean. This marked a strategic shift away from raiding and toward protecting his remaining ship and captured wealth on the return route.
Cavendish stopped at St Helena in the South Atlantic to gather supplies, a common practice on the route back toward Europe. Accounts describe his arrival on June 8–9, 1588, and the visit is often noted as an early (and sometimes claimed “first”) English landing on the island.
Cavendish arrived back at Plymouth in Desire, completing a full circumnavigation in a little over two years. The voyage became a landmark English privateering success: it combined global navigation with Pacific raiding and helped encourage later English efforts against Spanish maritime power.
Sir Thomas Cavendish's Circumnavigation (1586–1588)