The Portuguese Reach Calicut and Abyssinia

While Bartolomeu Dias negotiated Africa in 1487, and Christopher Columbus solicited support from Ferdinand and Isabella, King João II sent another expedition to the Orient using the Mediterranean route.

João had learned that the Knights Hospitalers of St. John of Jerusalem had captured Mehmet the Great’s heir to the Ottoman Empire. As a result, the Grand Master of the Knights Hospitalers was able to arrange a cease-fire between the Christians and the Turks, at least for the time being. Jerusalem experienced its first peace in hundreds of years. Venice, Castile, and other trading nations were rushing in to take advantage of the newly liberated opportunities in Middle Eastern markets.

When João learned about the cease-fire, he called a meeting of his lordly family council for a planning session. That counsel included his heir and nephew, Manoel of Viseu, who was Grand Master of Portugal’s Order of Christ. The council decided to send two men disguised as Muslims to the Levant for two purposes:

  1. to establish contact and relations with the Eastern Christians
  2. to investigate the possibility of diverting oriental trade from its current route through the Mediterranean to a route under Africa to Portugal.

You might have noticed that crossing the Ocean Sea westward was not on the agenda.

The council chose Pedro of Corvilhã to lead the expedition. Corvilhã spoke Castilian, Arabic, and Portuguese, and had spent time in the Muslim cities of Tlemeen [in today’s Algeria] and Fez [aka Fes, a market center south of Ceuta]. The council appointed one of King João’s squires in the Order of São Tiago, Antonio de Paiva, to accompany Corvilhã. Antonio de Paiva could speak Arabic.

The funding was to be provided by Bartholomeo di Domenico Marchionni, a wealthy Florentine banker living in Lisbon. Marchionni had made his fortune by renting the patent from King João to trade ivory in Guinea and Sierra Leon.

João’s cartographers, who had been supervised by the royal league of scientists known as the Junta dos Matemáticos, provided special maps.

The two emissaries crossed the Iberian peninsula to Barcelona, then shipped off to Rhodes, where the Grand Master of the Knights Hospitalers resided in a magnificent, well garrisoned castle. A Portuguese knight named Rui de Pina [who would later write a biography of King João II] met them at the dock. During their stop-over, the travelers invested in large quantities of Rhodes’ famous honey to barter in trade along their journey.

From there they sailed to Alexandria, Egypt. Their first obstacle was money. The honey they had spent a good portion of their funding on was nearly worthless in Egypt. Egyptians wanted wood for shipbuilding, iron, gunpowder, and sulfur. To make matters worse, the travelers came down with a horrible illness, from which they did not recuperate for months. Finally, in the spring of 1488, they were able to continue on to Aden.

Aden on the Arabian Peninsula, as you can see on the map above, was the terminus of seaborn traffic from the Orient. Her warehouses overflowed with pepper, camphor, aloe, cloves, cinnamon, cardamom, nutmeg, musk, velvets, silks, brocades, and tin from India and China.

While Pedro of Corvilhã stayed in Aden to investigate switching the shipping of goods around the African continent, Antonio de Paiva left to find Abyssinia and the African Christians. Unfortunately, he was “seen no more” [disappeared].

Corvilhã spent the next three years traveling. He sailed in a Muslim pilgrim ship from Aden to Cannanore [Kannur] off the Malabar Coast and became the first Portuguese person to set foot in India. He visited Calicut, Goa, and the great Arabian port of Ormuz [Hormuz]. He cruised with Arab traders up and down the east African Coast. Then he finally returned to Cairo in 1491 and learned that Paiva had disappeared and was probably dead.

Waiting for Corvilhã in Cairo were two Jewish men with messages from King João II. One man was a rabbi named Abraham of Beju. The other was a cobbler called Joseph of Lamego. Joseph had been to Ormuz before, so perhaps he was serving as a guide to Abraham. The letter the men carried informed Corvilhã about Bartolomeu Dias’ triumphant return. It also instructed him [and Paiva, not knowing he was dead] to press on to meet with the great king Prester John.

Corvilhã prepared a response to King João for Joseph of Lamego to take back to Portugal. Corvilhã informed King João that Paiva had gone missing; that he, Corvilhã, had reached the cities of Calicut, Goa, and Cannanor on the Malibar Coast; that he found cinnamon and pepper in Calicut; and that all could be had in Calicut except cloves, which came from beyond [the Spice Islands].

Corvilhã also encouraged his king to continue with the plan to send ships from Lisbon south past the Bay of Guinea and round the southern tip of Africa. From there, they were to sail north along the East African shore to a place called Sofala, which he thought was the name for the island we today call Madagascar. [Fra Mauro placed Soffola on the island’s western tip of Diab [Madagascar], marking it with a castle.]

Corvilhã wrote that the Muslims called Sofala [Madagascar], Island of the Moon, and told him it had 300 leagues of coast [the perimeter]. The Muslims also said that by traveling east from Sofala, a ship could lay a fair course to Calicut. [By Sofala, the Indians probably meant the trade market in Mozambique, the location of today’s Sofala province.] Those instructions would be very important to Vasco da Gama after he rounded the cape.

After Joseph left for Portugal, Corvilhã and Rabbi Abraham headed to Ormuz via Aden. There they parted. Rabbi Abraham stayed in Ormuz while Corvilhã headed to Abyssinia.

By that time, Corvilhã was “adept at passing as a Moor.” He sailed to Jeddah, visited the holy cities of Mecca and Medina [Mohammad’s birth place], said a prayer at St. Catherine’s monastery on the Sinai peninsula to ask forgiveness for passing himself off as a Muslim, continued to El-Tor on the Red Sea, and finally came to the chief port of Prester John’s Abyssinian kingdom, Zerla [today’s Dijbouti, shown on the map at the top of this article].

The Kingdom of Prester John

Believe it or not, Corvilhã finally met Prester John, or at least his contemporary representative. The last stretch of the journey was the most difficult. To reach Prester John’s tent city in the mountain valleys of Abyssinia – a mobile city that constantly moved from one place to another – Corvilhã traveled from monastery to monastery. Some of the monasteries hung from high cliffs. Some were nestled in lush green valleys. Corvilhã passed through scorching desserts, flash floods, narrow cliff paths, cave tunnels, and high mountain passes. He survived sword-slinging thieves and falling rocks.

When he finally reached the tent city, Corvilhã learned that the name Prester John was merely a generic term that the Europeans used to refer to the Christian Ethiopian king. The current Prester John was a fellow named Eskanda, and he usually spoke through messengers. On extremely special occasions, he spoke through a veil so that no one could see him. Eskanda was always guarded by four lions.

Eventually, after months of back and forth, Eskanda received Corvilhã. The meeting went pleasantly. But then Eskanda died. His successor, named Nahim, insisted on Abyssinian procedure. Just as the Mongolians treated Marco Polo well, but prevented him, his father, and his uncle from leaving Mongolia, the Abyssinians treated foreigners well, but never allowed them to leave Abyssinia. Corvilhã will not get tracked down until 1507, when a Portuguese priest named Francisco Alvares finally reaches him.

Fortunately, Corvilhã had already sent his important information back to King João with Joseph of Lamego. Meanwhile, Columbus will sail to America, John Cabot will sail to Newfoundland, Vasco da Gama will sail to India, and Pedro Álvares Cabral will discover Brazil. Corvilhã will marry and start a family, but we will tell you the rest later.

Back in Portugal, King João II kept busy managing his African explorers. He wanted to know if the Congo River led to Abyssinia. So, he had sent a group of missionaries to the Congo to find out. As they traveled up the river, the missionaries Christianized the natives they came across. Eventually the vast forests and feverish diseases prevented their progress. They sent a messenger to King João with word of their failure, which caused João’s subjects in Portugal to say, behind his back, that the king’s search for Prester John “was like a balked lion seeking his prey in a thicket of thorns and briars.”

So in 1491, when Joseph of Lamego arrived in Lisbon with the letter from Pedro of Corvilhã, João was elated. He was especially excited when he learned about the location of Sofala. With this information, Portuguese cartographers figured out that there was only 300 leagues of unknown territory between the last position reached by Bartolomeo Dias and the island of Sofala [Madagascar]. Covilhãs had mapped out the rest of the journey from Sofala to India.

João commissioned a wealthy nobleman named Estêvão da Gama(1) to prepare for a new expedition. Da Gama was a knight of the Order of São Tiago and had worked in the household of Fernando of Viseu, Henry the Navigator’s heir and João’s uncle. Fernando awarded Estêvão da Gama the alcaide mor [civil governor] of the coastal town of Sines(2) about a hundred miles south of Lisbon, probably for helping to chase the Moors out of the Algarve.

The sandy port of Sines [in the upper left corner of this map] was originally settled by Visigoths. It served as a fishing port during Roman times. The Order of São Tiago began to resettle the area in the 800s and in 1362 built a castle to guard against Muslim corsairs. As the alcaide mor, Estêvão da Gama collected taxes for the Order of São Tiago. He also became familiar with the African trade routes.

He and his wife, Isabel Sodré had five sons and one daughter: Paulo, João, Vasco, Pedro, Aires, and Teresa. The most famous will be Vasco.

King João ordered da Gama to sail past the place where Dias had turned back, continue to Sofala and then cross the Indian Ocean to Calicut. But da Gama will die before he can carry out his mission.

Death of Infante Afonso

One day in July of 1491, King João II suffered the most tragic event of his life. He was swimming in the Tagus River near his royal residence at Sacavén, when his sixteen-year-old son and only heir to the throne, Prince Afonso, rode down to accompany him. On the way Afonso was thrown from his horse and killed. The accident caused suspicion. Afonso had been an accomplished rider. But his valet, who was Castilian, and the only witness, mysteriously disappeared.

Prince Afonso was, at that time, married to Isabella of Aragon, the oldest daughter of Isabella of Castile and King Ferdinand of Aragon. The teenagers had been married since childhood to follow the edict of the Treaty of Alcáçovas-Toledo. But the Catholic Monarchs had been trying to get the marriage annulled.

Their only son and heir, Juan of Aragon, was weak in health. It did not seem likely he would live long enough to succeed his father, Ferdinand, and have a son and heir of his own. That would mean that Juan’s sister, Isabella, would become Queen of Aragon and Castile. As her husband, Prince Afonso of Portugal would become King of Aragon and Castile. And when King João II died [he was already suffering from the kidney problems that would kill him four years later], Afonso and Isabella would become King and Queen of Portugal as well as of Aragon and Castile. The Catholic Monarchs did not want that.

Now that Afonso was dead, King João had no legitimate heir, or any daughters to marry off. It is said he went into a depression from which he never recovered. His enthusiasm for exploration waned. The worst part for Portugal, and for progress toward finding a trade route to India, was that Prince Afonso’s death caused another succession war. This one included a battle between Portugal’s two leading military orders, the Order of Christ and the Order of São Tiago.

The two contenders to succeed King João II were:

  1. his cousin Manoel of Viseu, Duke of Beja, Master of the Order of Christ
  2. an illegitimate son, Jorge of Lancaster, whom João had conceived with a mistress, Ana de Mendonça.

Just FYI, Ana de Mendonça was the niece of Brites Furtado de Mendonça, the third wife of Bartolomeu Perestrello. Therefore, Christopher Columbus’s wife, Felipa, was related to Jorge of Lancaster by marriage.

Getting back to the succession problems, Jorge of Lancaster was a Knight of the Order of São Tiago. He was only six years younger than his half-brother Afonso had been. Jorge had been brought up by his mother in the castle of Joan of Portugal [the woman who had the illegitimate daughter Joanna]. Not surprisingly, Jorge’s existence, and the affair his mother, Ana, had with King João, caused a divide between João and his wife Leonor of Viseu.

Another problem was King João’s struggles against Manoel’s Order of Christ and its connection to Portugal’s high nobility. As we mentioned, João ordered the death of his brother-in-law Fernando IIand stabbed to death Diogo, Duke of Viseu. Those men were his wife Leanor’s father and brother. Manoel was also Leonor’s brother. The situation did not help João’s relationship with his wife one bit.

The debate about who would be the next king would go on for the next three years, until 1494. In the meantime, important things were happening in Spain.


  1. Estêvão da Gama was the eldest son (out of four) of Vasco da Gama of Olivença and Dona Teresa da Silva. We are not sure of the connection to the explorer da Silva.
  2. The Visigoths who settled there were known as Cinentos, hence Cine, hence Sine.

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