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In 1473, Columbus began his apprenticeship as business agent for the important Centurione, Di Negro and Spinola families of Genoa. Later, he allegedly made a trip to Chios, a Genoese colony in the Aegean Sea.^[18] In May 1476, he took part in an armed convoy sent by Genoa to carry a valuable cargo to northern Europe. He docked in Bristol, England^[19] and Galway, Ireland. In 1477, he was possibly in Iceland. In the autumn of 1477 Columbus sailed on a Portuguese ship from Galway to Lisbon, where he found his brother Bartolomeo, and they continued trading for the Centurione family. Columbus based himself in Lisbon from 1477 to 1485. He married Filipa Moniz Perestrelo, daughter of the Porto Santo governor and Portuguese nobleman of Lombard origin Bartolomeu Perestrello.^[20]

In 1479 or 1480, his son Diego Columbus was born. Between 1482 and 1485, Columbus traded along the coasts of West Africa, reaching the Portuguese trading post of Elmina at the Guinea coast.^[4] Some records report that Filipa died in 1485. It is also speculated that Columbus may have simply left his first wife. In either case, Columbus left Portugal for Castile in 1485, where he found a mistress in 1487, a 20-year-old orphan namedBeatriz Enríquez de Arana.^[21]

Ambitious, Columbus eventually learned Latin, Portuguese, and Castilian, and read widely about astronomy, geography, and history, including the works of Claudius Ptolemy, Cardinal Pierre d'Ailly's Imago Mundi, the travels of Marco Polo and Sir John Mandeville, Pliny's Natural History, and Pope Pius II's Historia Rerum Ubique Gestarum. According to historian Edmund Morgan,

Columbus was not a scholarly man. Yet he studied these books, made hundreds of marginal notations in them and came out with ideas about the world that were characteristically simple and strong and sometimes wrong, the kind of ideas that the self-educated person gains from independent reading and clings to in defiance of what anyone else tries to tell him.^[22]

Throughout his life, Columbus also showed a keen interest in the Bible and in Biblical prophecies, and would often quote biblical texts in his letters and logs. For example, part of the argument that he submitted to the Spanish Catholic Monarchs when he sought their support for his proposed expedition to reach the Indies by sailing west was based on his reading of the Second Book of Esdras (see 2 Esdras 6:42, which Columbus took to mean that the Earth is made of six parts of land to one of water). Towards the end of his life, Columbus produced a Book of Prophecies, in which his career as an explorer is interpreted in the light of Christian eschatology and of apocalypticism.^[9]