As we have seen, there were a number of factors that influenced Prince Henry's voyages of exploration. But along with these emerged another, more pragmatic, reason to explore. Although the Portuguese had long viewed the Atlantic as their major trading area and they had few business interests in the Mediterranean, Prince Henry saw Africa as a rich market teeming with natural resources and raw materials.

Portugal exported salt, wine, fresh and dried fruit, oil, honey, dried shellfish, cork, hops, and other raw materials to northern Europe in exchange for grain and flour, dried and salted fish, dairy products, metals, wood and other forest products for shipbuilding, textiles and other manufactured goods. Although the fifteenth and sixteenth centuries are noted as a period of expansion of European influence, it is important to note that this era of commercial and colonial expansion was not the first. In fact, commercial trade enjoyed a long and extensive history in the Mediterranean and the Atlantic, both in luxury items and articles of general consumption.

At the time of its conquest by the Portuguese, Ceuta was home to approximately 24,000 commercial establishments - some amounted to no more than market stalls - dealing in precious metals, silks, spices, and weapons, but since the Portuguese occupation of the city, trade gradually diminished to nothing. There were two ways to revitalise the city: either the Portuguese could establish a lasting peace with the North Africans, or they could conquer the territory around Ceuta to provide the city with an economic hinterland from which they could draw resources and markets. Because conflict between Islam and European Christianity prohibited a lasting peace from being established, in later years the Portuguese would try to gain control of the economic hinterland with disastrous results.

As we have seen, there were a number of reasons that Prince Henry began his voyages of exploration. Azurara, one of Prince Henry's contemporaries and chroniclers, summarised them as:

The collapse of the Roman Empire in the fifth century did not bring with it the decline of commerce and trade in North Africa. Indeed, control of trade had merely fallen into local hands. When Portugal attempted to re-enter the North African trade, they discovered that they had to rely on a great number of intermediaries to do business, denying them the indispensable source of travel to gather information about African geography. The capture of Ceuta in 1415 meant, however, that Portuguese settlers were exposed to a larger number of stories about the interior of Africa. Denied the opportunity to explore the interior of Africa by land, Henry began to set his mind to an alternate approach; instead of exploring Africa directly, Prince Henry would attempt an encirclement, and would explore Africa by sea.

The two captains Prince Henry chose for his first expedition to explore Cape Bojador were not experienced sailors. Perhaps the selection was deliberate, for it seemed unlikely that any experienced sailor who had come into contact with the myths and legends surrounding sea travel would willingly sail into the unknown. Even more importantly, as one historian has pointed out, Portuguese mariners were not used to sailing out on the open sea; their nautical experience was limited to coasting in sight of land.

Not only did Prince Henry not accompany those first ships on their exploration of Cape Bojador, he did not go on any of the successive voyages, and this has led to some spirited debate among historians about how Prince Henry's role in the exploration of Africa should be interpreted. Does Prince Henry, as some have suggested, deserve a prominent place in history for providing the intellectual and financial stimulus for the voyages to take place? More recently, historians have suggested that Prince Henry did not play an active role in the exploration of Africa. Some have intimated that this would indicate that Prince Henry was a coward who feared the physical risks and dangers entailed by exploration. But others have replied that the courage the Prince displayed during the Ceuta campaign would seem to belie this explanation.

Clearly, there are many issues that must be dealt with before an adequate explanation can be found of why Prince Henry did not join the explorations. Perhaps it was the risk of being captured by North African pirates that prevented Prince Henry from taking a more active role, even though Portuguese ships were armed and no ship of Prince Henry's fell victim to pirates. Others, choosing to emphasise the positive aspect of Henry's preference to remain in Portugal conclude that the Prince's self-sacrifice was extraordinary. It was Henry's task to plan the expeditions and to assess and analyse the reports brought home. According to this perspective, it was only by remaining objective that Henry would be able to accurately sift through information gathered by the explorers, to separate truth from fiction, and to plan subsequent voyages. Perhaps the most plausible explanation regarding Henry's decision to remain at Sagres is that fifteenth century custom deemed activities, like living with a number of sailors in close quarters for months on end, to be beneath a prince. Granted, while others of noble descent did take part in the voyages, and given the fact that Prince Henry camped with his troops during military campaigns, squeamishness about close contact with sailors seems difficult to accept.

As word spread throughout Europe of the Portuguese expeditions, sailors, astronomers, cartographers, and geographers began to arrive at Sagres to offer their services to Prince Henry. There were Christians, Jews, and Arabs - Prince Henry had discovered the Arabs' superior navigational skills while at Ceuta years before - and what emerged at Sagres was not so much a school of navigation as much as it was a community of scholars, under the direction of Prince Henry, who joined together to conquer the unknown.

When Prince Henry's ships returned from their first exploration, their captains reported that they were unable to round Cape Bojador as planned. Shortly after losing sight of Cape St. Vincent, they were caught in a violent gale and lost all sense of direction. They drifted for days when the winds abruptly died. By sheer luck the crew sighted land, and the intrepid explorers made their way toward shore and a sheltering cove and they named this island Porto Santo ("blessed port"). As best as they could determine, Porto Santo was roughly five hundred miles to the southwest of Cape St. Vincent. The "discovery" of Porto Santo was significant because it was then used as a launching point for future voyages. It should be noted, however, that there is some reason to question whether or not Porto Santo was discovered by Prince Henry's ships, for the island's location coincides with one marked on a Genoese map made in approximately 1351. Nevertheless, the Portuguese believed that they had found a previously uncharted land mass, and armed with the information that there was land yet to be discovered, another expedition set out before the end of 1419. On this voyage, they encountered the island Madeira (Portuguese word for "wood") in the early months of 1420.

Prince Henry displayed remarkable perseverance and sent expedition after expedition into the "Sea of Darkness", as they called unknown water, in a fifteen-year attempt to round Cape Bojador. Even though he exhorted his captains with promises of increased reward and glory, it was not until 1434 that Gil Eanes (sometimes spelt "Eannes") managed to round the Cape. The physical distance travelled was not what was significant about this voyage. Rather, what was important was that Gil Eanes traveled beyond Cape Bojador and returned to Portugal, eliminating in one broad stroke many of the myths and legends about the "Sea of Darkness".

A number of explanations have been offered as to why it took Portuguese sailors so long to accomplish this task. The two most significant problems were that those ships which navigated along the shores of the African coast risked running aground and those who attempted to steer into the open water and strayed too far could be blown out to sea. Eanes succeeded because he did not attempt to sail in sight of land. Rather, Eanes charted a wide course into the Atlantic before altering his course and turning back towards Africa. When Eanes encountered land again, Cape Bojador was behind him.

The exploration of Africa occupied a great deal of Prince Henry's time and attention, a past conquest soon became a pressing issue. The Portuguese colony at Ceuta was rapidly becoming a drain on the national treasury and it was realised that without the city of Tangier, possession of Ceuta was worthless. When Ceuta was lost to the Portuguese, the camel caravans that were part of the overland trade routes began to use Tangier as their destination. This deprived Ceuta of the materials and goods that made it an attractive market and a vibrant trading locale, and the city rapidly became an isolated community. The cost of garrisoning generated further losses, a situation that might be reversed if Portugal were to capture Tangier. There was, however, another reason to launch a military campaign against Tangier. Prince Fernando, Prince Henry's youngest brother, was only eleven years old when the Portuguese captured Ceuta and he had not won his spurs in battle like his older brothers. After much prodding, and some court intrigue, Prince Henry managed to convince his brother to begin preparations for an attack on Tangier in 1436.

In stark contrast to the attack on Ceuta years before, the Portuguese assault on Tangier was poorly conceived and badly executed. When the Portuguese fleet set sail in August 1437, it contained only 6,000 troops; Portuguese planners originally estimated that it would take 14,000 soldiers to comprise an adequate striking force. Furthermore, no attempt was made by Prince Henry to disguise his intention to attack the city, and the North Africans were well prepared to turn back the Portuguese. Three times Prince Henry attempted to assault the city, and all three times his armies were repulsed. Only after his chaplain deserted him and told the North Africans the details of the new assault did the full measure of the futility of his attacks grip Prince Henry. Realising that his position was hopeless, Prince Henry asked the North African leader, Sala-ben-Sala, to dictate his terms for surrender. The North African's terms were decidedly harsh. Not only would the Portuguese have to agree to an exchange of hostages - Prince Henry's brother, Prince Fernando, for one of Sala-ben-Sala's sons - but the Portuguese would have to abandon the city of Ceuta. The exchange of hostages was a show of good faith easily agreed upon by the two leaders but it soon became clear that Sala-ben-Sala would have to wrestle Ceuta from the Portuguese. Sala-ben-Sala declared that the Portuguese would have to abandon Ceuta before Prince Fernando would be released. When the Portuguese protested, and reminded the North Africans that they were holding one of the king's sons, Sala-ben-Sala replied that he had many other sons and that he did not particularly care for the one the Portuguese were holding. Thus, Prince Henry had to make a decision, either he could sacrifice the city of Ceuta to obtain his brother's release, or he could keep Ceuta and condemn Fernando to imprisonment. The city of Ceuta was deemed to be an important outpost of Christianity against the infidel and even the Pope advised against trading Ceuta for Prince Fernando's life. The city could not be sacrificed for one man, even for the brother of the king of Portugal. Needless to say, Prince Fernando died in captivity four years later.

Prince Henry returned devastated from the debacle at Tangier. After nearly a year had passed, Prince Henry resumed his exploration of the sea and some of his associates believed that his new-found vigour owed a great deal to the failure at Tangier. It was almost as if Prince Henry believed he could avenge the defeat and humble the Muslims by conquering the whole of Africa. Moreover, Prince Henry committed himself to finding the fabled Prester John in order to bring the battle directly to his enemies. An incredible patchwork of hearsay and rumour contributed to the legend of Prester John but what was significant about Prester John for Prince Henry was not the land of riches that could be found within the borders of Prester John's kingdom, but the belief that a Christian king had managed to establish and sustain an empire in the heart of Muslim-held territory. Therefore, locating Prester John meant delivering a devastating blow to the Muslims.

Another expedition was sent out in 1441 to "make peace" with the indigenous populations of North Africa. But rather than "make peace" with the Africans as Prince Henry had ordered, ten prisoners were taken. One of the prisoners happened to be the chief of the tribe by the name of Adahu. Fortunately for the Portuguese, Adahu spoke Arabic and could communicate with the Bedouin translator. The captain decided to bring back Adahu as a prize for Henry. Before returning to Portugal, the ship's captain sailed further down the coast until he encountered a headland of white cliffs, which he named Cabo Branco (Cape Blanco).

Upon returning to Sagres, Adahu described what he knew of Africa and the land-based trade routes. The questioning of Adahu was undoubtedly an exciting exercise for Prince Henry; for the first time since the capture of Ceuta, Prince Henry was able to verify the information gathered by explorers with Adahu's first-hand knowledge. The capture of Adahu also marked the beginning of the use of the indigenous population as interpreters for subsequent voyages.

An envoy was sent to the Pope to report the information gathered by Prince Henry and to request that the Portuguese Prince be granted spiritual jurisdiction over all the lands he "discovered" to the south. Prince Henry also wanted that those who lost their lives on these voyages be considered to have died while on a crusade. The Church agreed and these concessions were matched by the Portuguese monarch. Prince Pedro granted Prince Henry a charter that entitled Henry to one-fifth of the profits of the expedition, normally a prerogative reserved for the Crown. Prince Pedro also stipulated that all captains sailing down the African coast must first seek Prince Henry's permission.

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