De With was born on a farmstead in the hamlet of Hoogendijk near
Brielle or Brill, the very town in which
Maarten Tromp had been born a year earlier. According to legend, they were friends or even already rivals in their youth, but there is no proof of this. His father died in 1602, leaving behind three sons, besides Witte also Abraham and Andries, and a daughter Catharina. The De With family were
Mennonites and strict
pacifists; in 1610, Witte, as an
anabaptist not yet baptised, obtained a
baptism by a
Calvinist preacher so that he would no longer feel constrained in using violence, as he was by nature not a peace-seeking boy. After some failed minor jobs, he went on his first sea voyage to the
Dutch East Indies on 21 January 1616 when he was sixteen, as a cabin boy on Captain Geen Huygen Schapenham's ship the
Gouden Leeuw, part of a
Dutch East India Company (VOC) fleet of five vessels. He arrived at
Bantam on 13 November 1616. Until October 1617, he participated in two trade voyages to
Coromandel in
India. Afterwards, he became manservant of governor
Jan Pieterszoon Coen. He served as a
corporal during the siege of
Jakarta in 1618. On 8 October 1618, he sailed home on the
Gouden Leeuw, returning to Brill on 23 May 1619. On 20 August 1620, he took service with the
Admiralty of the Maze as a
schipper (then the highest NCO rank), still under Schapenham on the
Gelderland. From December 1620, the
Gelderland participated in an expedition by Admiral
Willem Haultain de Zoete against the
Barbary Corsairs, returning in August 1621. In spring 1622, De With was appointed lieutenant on Schapenham's vessel. When the latter became ill, De With functioned as
commandeur, acting captain, of the
Gelderland during convoy duty in the
Baltic. When Schapenham recovered, De With served for a short period on the
Maurits to protect the herring fleet. In July 1622, De With became flag captain of
Delft of now Vice-Admiral Schapenham, who, from 29 April 1623, carried out the spectacular raid organised by the
Admiralty of Amsterdam, sending the so-called "
Nassau fleet" against the Spanish possessions on the west coast of America; this fleet rounded
Cape Horn in March 1624. On his first voyage as a captain, De With already showed he was the strict disciplinarian of later legend: on 13 April, six of his men deserted his ship and the constant beatings and floggings to flee to the uninhabited island of
Juan Fernández. Until October, the fleet attacked Spanish shipping and settlements; during one of the actions, De With was wounded by a musket bullet. Then, it crossed the
Pacific, sailing via the
Mariana Islands to the Indies. Reaching
Ternate in the
Spice Islands on 5 March 1625, De With, himself on request of the governor of
Ambon in a punitive action, laid waste to the island, destroying by his own count 90,000
clove trees of the inhabitants, to increase the price of this commodity. He departed for the Republic on 6 February 1626, after the death of Schapenham, as Vice-Admiral (in service of the
Verenigde Oostindische Compagnie) of a Spice Fleet of four ships, then worth five million guilders. He returned on 22 September 1626, thus having circumnavigated the globe, a feat in which he took much personal pride. On his return, he learned that his mother and sister had died; he remained on shore for one and a half years. == Capture of Spain's treasure fleet ==