He was a native of Covilhã in Beira. In his early life he had gone to Castile and entered the service of Don Juan de Guzmán, brother of Enrique de Guzmán, 2nd Duke of Medina Sidonia. Later, when war broke out between Castile and Portugal, he returned to his own country, and attached himself, first as a groom, then as a squire, to Afonso V of Portugal and his successor John II of Portugal. In 1487, his overland expedition made its way to India, exploring trade opportunities with the Indians and Arabs, and winding up finally in Ethiopia. His detailed report was eagerly read in Lisbon, as Portugal became the world's best informed center for global geography and trade routes.