In 1487, King John sent Pedro de Covillan and Alphonzo de Payva, both of whom could speak Arabic, to discover India by land. They left Lisbon in the month of May, and took shipping in the same year at Naples for the island of Rhodes, and lodged there in the hotel of the Knights of St John of Jerusalem, belonging to Portugal. From thence they went to Alexandria and Cairo, and then along with a caravan of Moors to the haven of Toro. There they embarked on the Red Sea, and proceeded to Aden, where they separated; de Payva going into Ethiopia, while Covillan proceeded to India. Covillan went to the cities of Cananor and Calicut, and thence to Goa, where he took shipping for Sofala, on the eastern coast of Africa. He thence sailed to Mosambique, and the cities of Quiloa, Mombaza, and Melinda, returning back to Aden, where he and Payva had formerly separated. Thence he proceeded to Cairo, where he hoped to have rejoined his companion; but he here learnt by letter from the king his master, that de Payva was dead, and he was farther enjoined by the king to travel into the country of Abyssinia86 He returned therefore, from Cairo to Toro, and thence to Aden; and hearing of the fame of Ormuz, he proceeded along the coast of Arabia by Cape Razalgate to Ormuz. Returning from the Gulf of Persia to the Red Sea, he passed over to the realm of the Abyssinians, which is commonly called the kingdom of Presbyter John, or Ethiopia, where he was detained till 1520, when the ambassador, Don Roderigo de Lima, arrived in that country. This Pedro de Covillan was the first of the Portuguese who had ever visited the Indies and the adjacent seas and islands.

In the year 1490, the king sent Gonzalo de Sosa to Congo with three ships, carrying back with him the ambassador of the king of Congo, who had been brought over to Portugal in 1484, by Diego Caon. During his residence in Portugal, this ambassador and others of his company had been instructed in the Christian religion, and baptized. Gonzalo de Sosa died during the outward-bound voyage; and Ruy de Sosa, his nephew, was chosen to the command of the expedition in his stead. Arriving in Congo, the king of that country received them with much joy, and soon yielded himself and the greater part of his subjects to be baptized; to the infinite satisfaction of the Portuguese, who by these means converted so many infidels from paganism to Christianity.

In the year 1492, when Don Ferdinand king of Castile87 was engaged in the siege of Granada, he sent one Christopher Columbus, a Genoese, with three ships, for the discovery of Nova Spagna. This Columbus had first offered his service lot a western discovery to John king of Portugal, who refused to employ him. Being sufficiently furnished for his enterprize, Columbus set out from the town of Palos on the third of August 1492, having with him, as captains and pilots, Martin Alionzo Pinzon, Francis Martinez Pinzori, Vincent Yannes Pinzon, and Bartholomew Columbus his brother88 with an hundred and twenty other persons in the three ships. Some persons affirm, that this was the first voyage which was ever conducted by the observation of latitudes89. They took the Canaries in their way, whence shaping their course for Cipango, or towards Japan, they were much amazed to find the sea all full of weeds, and with great fear arrived at the Antilles on the tenth day of October; the first island they descried, called Guanahany by the natives, they named San Salvador. This island is in 25° N. latitude. After that they found many islands, which they called the Princes. The savages of those parts call these islands by the name of Lucaios, having indeed several names for them, and they stand on the north side of the line, almost under the tropic of Cancer. The island of St James, or Jamaica, lies between the 16th and 17th degrees of northern latitude90. Thence they went to the island which the natives call Cuba, named Ferdinando by the Spaniards, after the king, which is in 22 degrees; from whence they were conducted by the Indians to another island called Hayti, named Isabella by the Spaniards, in honour of the queen of Castile, and afterwards Hispaniola, or Little Spain.

In that island the admirals ship was wrecked, and Columbus caused a fort to be constructed of her timbers and planks, in which he left Roderigo de Arana with a garrison of thirty-eight men, to learn the language and customs of the country. Columbus then returned to Spain, carrying with him samples of gold and pearls, and other productions of the country, with ten Indians, six of whom died on the voyage; the rest were brought to Spain and baptized. On their way home, Columbus touched at the Açores; and on the fourth of March 1493, entered the port of Lisbon. This discovery gave much discontent to the king of Portugal. Immediately on his arrival, Columbus went into Castile, where he informed the king of his discoveries and of the dissatisfaction of the king of Portugal. On this he and his queen Isabella sent word of the recent discovery to Pope Alexander VI, at which information he and all the Italians were much astonished, as they marvelled that there should be any land besides what had been known to the Romans. Alexander made a grant of all these countries to the crowns of Castile and Leon, under condition that they should labour to extirpate idolatry, and establish the holy faith of Christ among the natives.

On the report of this discovery, so universal a desire of travelling arose among the Spaniards, that they were ready as it were to leap into the sea, that they might swim if possible to the newly discovered islands. After receiving the authority of the Pope, King Ferdinando sent Columbus a second time to the newly-discovered country, of which he made him admiral, giving him many other honours, and a particular coat of arms, having this motto,

Columbus set out on his second voyage to the Antilles on the 25th October 1493, taking his course from Cadiz, with seventeen ships and fifteen hundred men, accompanied by his brothers Bartholomew and Diego Columbus, with many other knights, gentlemen of the law, and priests; having chalices, crosses, and other rich religious ornaments, and with great power and dignity from the Pope. The tenth day after commencing their voyage, they reached the Canaries; and from thence, in twenty-five or thirty days, they sailed to the Antilles, the first island they saw being in 14° N. due west from Cape de Verd in Africa. They called this island Deseada92, or the desired island, which is said to be 800 leagues from the Canaries. They afterwards discovered many more islands, which they called the Virgins, but which are named the Caribbee islands by the natives, from a nation of that name, who are bold warriors, and excellent marksmen with bows and arrows. They poison their arrows with the juice of a certain herb, and whoever is wounded with these is sure to die, biting himself like a mad dog. From thence they went to the principal island in these parts, named Boriquen by the natives, and St John by the Spaniards; and thence to Hispaniola, or Isabella, where they found all the men dead whom they had left on returning from the former voyage. Columbus left most of his people here to establish a colony, under the command of his brothers; and went with two ships to continue his discovery of Cuba and Jamaica. All these islands are between 16 and 20 degrees of northern latitude93. While the admiral was sailing in quest of discoveries, his brethren and those who were left in Hispaniola, were much incommoded by an insurrection among the savages; and Columbus went back to Spain, to give an account of his proceedings to the king and queen.