Cornelis de Houtman was taught navigation in Amsterdam by Robbert le Cannu. He and his brother Frederik were sent to Lisbon by a group of nine Amsterdam merchants towards the end of 1592 to gather information about the sea route to the East and trading prospects there. Such information was kept secret by the Portuguese in order to maintain their monopoly on trade. The brothers were arrested, but were released after their bail had been paid from Amsterdam. They returned to Holland in 1594. The merchants founded the "Compagnie van Verre (Landen)" and appointed Cornelis De Houtman as supercargo of the first ever Dutch trading expedition around the Cape to the East. He sailed in April 1595 from the island of Texel with four ships, using a manuscript by J.H. van Linschoten as his guide. The latter had passed the Cape without landing in 1583. Decisions regarding the voyage were made by a sea council, of which De Houtman was a member. He was not a good leader and his uncouth behaviour resulted in repeated clashes with the heads of the fleet, over which he had no authority.
The expedition landed only once on southern African soil, at Mossel Bay. Several brief descriptions of this visit were written by different individuals, the best one by Willem Lodewijckz. These were included in various editions of an account of the expedition (perhaps written by De Houtman), of which English and French translations were published as early as 1598. The book includes a map including southern Africa which is, however, of poorer quality than earlier Portuguese maps. An illustration on the map depicts several kinds of sea birds and fish, as well as a crude rendition of the seaweed Ecklonia maxima - the first known illustration of a South African plant. The ships passed the Cape and arrived at present Mossel Bay on 4 August 1595, staying for a week. They bartered with the local Khoi, exchanging sheep and cattle for pieces of iron. De Houtman is credited with the first known measurement of magnetic declination carried out on South African soil, finding it to be zero at their landing place (Beattie, 1909, p. 5).
The expedition touched at Madagascar and proceeded to Indonesia, where De Houtman hoped to find the Sunda Strait, between Java and Sumatra, in order to reach the Moluccas. They eventually reached Java in June 1596 and travelled through the Sunda Strait towards the south of Java. After many misfortunes three of the ships returned to Holland in August 1597 without landing in southern Africa. The venture produced no immediate gain, but was soon followed by many other Dutch trading expditions that led to the formation of the Dutch East India Company.
In 1598 De Houtman and his brother were employed by ship-owner Balthasar de Moucheron and again set sail for the East in charge of two ships. The pilot of the expediton was the English navigator John Davys, who wrote a description of the voyage. Though better prepared than on his first expedition, De Houtman again showed poor leadership. His ships anchored in Table Bay in November 1598 to barter for cattle, but fighting broke out with the local inhabitants during which 14 members of the expedition were killed. Shortly after his arrival in northern Sumatra De Houtman was killed aboard his own ship by a party of Indonesians.