Portugal and Western Africa have built a common history since the middle of the fifteenth century. In this century the Portuguese maritime expansion was a pioneer movement within the European expansion process. It established an uninterrupted connection between societies that had never met before. After a short period of Portuguese warlike activities (1436-48), the African resistance to enslavement, inter alia, forced a radical change of strategy. By 1460 the Portuguese had explored the western African coast as far as the present Sierra Leone, and had begun to establish with African societies a fairly peaceful relationship founded on mutual trade interests. Within this context, Christianity, although it might be faced in a different way by each culture, constituted a common “language,” a path to find approaching ground and fulfil reciprocal needs.From the beginning, the Portuguese Crown attempted to establish a monopoly on the European coastal and riverine activities, an attempt that was progressively challenged, in loco, by the French, the English and the Dutch, during the sixteenth and seventeenth centuries. But the State interests were also challenged by illegal private traders that came both from the Iberian Peninsula and Santiago Island and had their own agents in Guinea.The geographical basis for trade activities (legal and illegal) were, at least until the 1560s, the Cape Verde islands, which were discovered ca. 1460-1462. Trade—together with the strategic value of the archipelago to the Atlantic navigation—was the reason why the colonization of the main island, Santiago, began very early, in 1462, followed, at the end of the century, by Fogo island.