The Portuguese begin mapping and exploring the South African coastline and basic trading takes place between the Khoikhoi and the Europeans. Nguni and Sotho speaking groups begin colonizing South Africa (subjecting and incorporating neighboring groups and dispossessing their land), with eventually only the western and northern areas of the Cape not dominated by them.
- The power of the Portuguese nation begins to decline. This marks the start of many European nations pursuing the sea route rather than the land route to India.
- Antonio de Saldanha, leading a Portuguese squadron, enters Table Bay (called Aguada da Saldanha until 1601) owing to a navigational error. They are the first Europeans to climb Table Mountain, which they name Taboa do Cabo (the Table Cape) on account of its shape.
- 1 March, On his way back to Portugal the Viceroy of Portuguese India, Francisco d' Almeida, is killed in a skirmish with Khoi-Khoi, probably due to a misunderstanding arising from barter between the Khoi-Khoi and the Portuguese at the mouth of the Salt River in Table Bay. Thereafter, Portuguese traders tend to bypass the Cape itself, relying on Robben Island for fresh meat and water.
- 24 April, The Portuguese ship São Bento is wrecked north of the Great Fish River on its return from the East. Manuel de Mesquita Perestrelo, Portuguese navigator and cartographer is one of 64 survivors of the crew of 473 who reaches Delagoa Bay on foot, and one of 23 to be ultimately rescued.
- An account of the shipwreck of the São Bento by mariner Manuel de Mesquita Perestrelo is published in Portugal, the oldest book dealing exclusively with events on South African soil.
- Portuguese mariner and cartographer Manuel de Mesquita Perestrelo explores the south and south-east coast of South Africa on a voyage for this purpose. He gives the first detailed description and draws a map of the coast.
- 18 June, An English admiral, Francis Drake, rounds the Cape on his voyage round the world in his quest to reach India for the English Crown. He describes the Cape in the following words: 'This Cape is a most stately thing, and the fairest Cape we saw in the whole circumference of the earth.'
- The English and the Dutch begin to call regularly at Table Bay on their way to and from Asia. Khoikhoi traded mainly iron, copper and marijuana with the foreigners at this stage.
- 1 August , The English navigator, James Lancaster, barters sheep in the Bay of Saldaha (called Table Bay after 1601) from the Khoi-Khoi. He describes the sheep as very large, with good mutton, bearing no wool but hair, and with very large tails.
- 4 August, Four ships under Cornelis de Houtman reach São Bras. This is the first contact of the Dutch with the coast of Southern Africa.
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