In 1415, the Portuguese occupied the North African city of Ceuta, aiming to gain a foothold on Morocco, to control navigation through the Strait of Gibraltar, expand Christianity with the backing of the Pope, and by pressure of the nobility for epic and profitable acts of war, now that Portugal had finished the Reconquista on the Iberian Peninsula. Among the participants of the action was the young Prince Henry the Navigator. Appointed governor of the Order of Christ in 1420, while personally holding profitable monopolies on resources in Algarve, he took the lead role in encouraging Portuguese maritime exploration until his death in 1460. He invested in sponsoring voyages down the coast of Mauritania, gathering a group of merchants, shipowners, stakeholders and participants interested in the sea lanes. Later his brother Prince Pedro granted him a royal monopoly of all profits from trading within the areas discovered.

In 1418, two of Henry's captains, João Gonçalves Zarco and Tristão Vaz Teixeira were driven by a storm to Porto Santo an uninhabited island off the coast of Africa which may have been known to Europeans since the 14th century. In 1419 Zarco and Teixeira made a landfall on Madeira. They returned with Bartolomeu Perestrelo and Portuguese settlement of the islands began. There, wheat and later sugarcane were cultivated, as in Algarve, by the Genoese, becoming profitable activities. This helped both them and Prince Henry become wealthier.