Empires of the Monsoon. Richard Hall

The senior of the two agents, named Pêro de Covilham (sometimes written Covilhã or Covilhão), had been given a chart on which he was ordered to note down everything the two managed to learn about navigation in the Indian Ocean.¹ In particular, he had been told to find out whatever the Arab and Indian sea-captains might know about a route round the southern tip of Africa.

      On the day of their departure, Covilham and his companion, Afonso de Paiva, had been assured by the Portuguese king, John II, that he knew they were embarking on a ‘difficult mission’. This was an understatement. Although both spoke Arabic, were using Muslim names, and had assumed the appearance of itinerant merchants, the price of having their identities discovered would almost certainly be death; the best they could hope for, if they were found out, would be enslavement. To ensure they had perfected their new roles they took time over the journey from Portugal to Egypt, by way of Valencia, Barcelona. Naples and Rhodes, where they boarded a ship for Alexandria with their jars of honey.

      From that moment on there was no way of sending messages back to Lisbon, other than risking the use of a slow and uncertain courier system maintained between Jewish merchants in Europe and their compatriots in the lands of the East. There was a large Jewish community in Cairo, which had been the foremost city in the Muslim world until Constantinople was captured by the Turks some thirty-five years earlier; it was to Cairo that Covilham and Paiva planned to return when their work was complete. Now their aim was to travel up the Nile, cross to the Red Sea with a trading caravan, then take a boat down to Aden at the entrance to the Indian Ocean.

      Selling honey as they went, they reached Aden safely in August 1488, and there agreed to part. They would never see one another again, and neither would return to Portugal. Paiva crossed over to the port of Zeila on the African mainland, to make his way into Ethiopia. This was a hazardous route for a Christian disguised as a Muslim, since it went through territory occupied by the Arab armies who were confronting the Ethiopians in their mountain fastnesses.

      Now on his own, Covilham booked his place in one of the hundreds of small Arab dhows leaving at that season from Aden to India, with the south-west monsoon in their sails. This was to be the first of a series of journeys that would last more than two years, as Covilham repeatedly criss-crossed the Indian Ocean, furtively making notes on the chart he kept in his baggage.

      Behind him lay a career in espionage and diplomacy which made him a natural choice for such a venture. By now in his late thirties, he had risen from poverty to be a knight in the royal household. His birthplace, from which he took his name, was the mountain town of Covilham, close to the border with Spain. In his youth he had served in the court of the Castilian duke of Medina Sidonia, but returned to Portugal in 1474. A natural linguist, he accompanied King Afonso V on a visit to France, and so impressed his superiors that he was sent back to France on his first espionage mission. One of his contemporaries described him as ‘a man of great wit and intelligence’, and a vivid raconteur. Covilham was taken up by John II, who sent him to Morocco as an ambassador. There his task was to negotiate with the sultan of Fez for the return to Portugal of the bones of the ‘martyr’ Prince Fernando, who had died in a Moroccan dungeon after being captured at Tangier in 1437. This spell in Morocco allowed Covilham to master Arabic and study the Islamic way of life.

      What had especially endeared Covilham to the new king was the work he next carried out; he was sent to Castile to keep an eye on the activities of the fugitive Braganza family.² As a chronicler put it, John II wanted Covilham to ‘spie out who were those gentlemen of his subjects which practised there against him’. The hatreds around the throne at the time were intense, for the king had ordered the execution of his cousin the Duke of Braganza for plotting, and had personally stabbed to death another disloyal duke, notwithstanding that he was the queen’s brother. Amid this royal blood-letting, Covilham always stayed true to the king.

      The decision to send spies to the East had been taken early in 1487, and simultaneously three caravels were being prepared for a decisive effort to reach the southern end of Africa and find a way into the Indian Ocean. This was the culmination of seventy years of Portuguese effort, during which geography had proved a far more frustrating obstacle than could ever have been imagined by the long-dead Prince Henry. Already the voyages of exploration went as far beyond the equator as Portugal was to the north of it, yet still the African coastline ran due south.

      The Portuguese captains continued to put up stone pillars, surmounted by crosses, on prominent headlands. These landmarks in the unknown were reassurances to the men who came by on subsequent voyages, and challenged them to go further. The captains were always anxious about the moods of their crews, in cramped and comfortless ships amid stormy seas. The greater the distance from Europe, the greater the risk of mutiny. Superstitious sailors feared they might sail off the end of the world into oblivion.

      The tested and resourceful captain chosen to lead the three caravels to the end of Africa was Bartolomeu Dias. Although Covilham must have known him, or at least have heard of his plans, there is little likelihood that they would have discussed the chance of meeting somewhere in the Indian Ocean during their respective journeys. With success seemingly so close, and fears of Spain’s jealous rivalry so strong, few confidences were exchanged in Lisbon during the fifteenth century’s closing decades.

      The small group who gave Covilham and Paiva their final instructions met in ‘great secrecy’ in the house of an aristocrat, Pêro de Alcacova. Present were the future king, Manuel, then Duke of Beja, and two Jewish ‘master doctors’, Moses and Roderigo. One of these was a royal physician, and both were renowned cosmographers. The importance plainly being attached to the covert expedition shows how the Portuguese still feared there were unknown hazards which might yet snatch away success. The orders to make contact with ‘Prester John’ equally reflected the hope of forging an alliance with a friendly monarch whose ports could offer safe havens to the Portuguese caravels.

      Seemingly never in doubt was the prospect of ‘breaking through’ to the Indian Ocean. The two cosmographers told Covilham that they had found a document (nothing more is said about it) regarding the passage between the Indian Ocean and the Atlantic. The existence of Sofala, the southernmost port on the eastern coast of Africa, was by now well known – although it had never been seen or described by any European – and that was one of the places Covilham knew he must visit in due course.