Christopher Columbus who was in all probability from Genoa, in Italy, is believed that his connection with the Madeira Islands is closely related with the sugar trade, which had intensified at this time. In 1478, Columbus came to the Madeira Islands, employed by Paolo di Negro as an intermediary in the sugar trade, with Ludovico Centurione.
Between 1479 or 1480, other connections reinforced Christopher Columbus connections with Madeira Islands, particularly with his marriage to Filipa de Moniz, daughter of Isabel Moniz and Bartolomeu Perestrelo, first captain-donee of Porto Santo. Although it has not been proven, there are various versions and explanations regarding this marriage, the most likely being that Columbus' ancestors and those of his father-in-law, Bartolomeu Perestrelo, were originally from the region of Placência (Italy).
Since Christopher Columbus was on the Madeira Islands (1480-1482), time when the Portuguese discoveries and exploration of the West coast of Africa were well under way, it's assumed that this was where he obtained his basic nautical training, information which later became essential for his expeditions on behalf of the Court of Spain, in search of the maritime route to India. On the other hand, Porto Santo was also a strategic point, since it was often used as a refueling port for passing ships.
As he progressed on his voyages of discovery, there are reports of the presence of on the islands and of his stopover at Porto Santo around 1498, on the way to his third voyage to America.