While the admiral remained at Seville attending to the equipment of the expedition, he received a letter from their majesties, directing him to cause a sea chart to be drawn with all the rhumbs and other particulars necessary for pointing out the voyage to the West Indies. Their majesties pressed him to hasten his departure, making him great promises of favour and reward, as the importance of his discovery seemed every day the greater. This letter was dated from Barcelona on the 5th September, up to which day nothing had been definitively settled with the king of Portugal, respecting the proposed limits between the two nations in the ocean. The admiral continued his exertions to get every thing ready, and caused many kinds of useful plants to be shipped; likewise wheat, barley, oats, rye, and all kinds of grain and seeds; cows, bricks, lime, and other materials for building; and an infinite number of useful articles.
Every thing being in readiness, the stores all shipped, and the men embarked, the fleet set sail from the bay of Cadiz on Wednesday the 25th of September 1493 before sunrise. The admiral directed his course to the south-west for the Canary islands. On Wednesday the 2d October the fleet came off the island of Gran Canaria, and on Friday the 5th came to anchor at Gomera, where the admiral remained two days taking in wood and water, and procuring cattle, sheep, goats, and swine, for the intended colony in Hispaniola. Among these he purchased eight sows for 70 maravedies each, from which all those which have since stocked the Indies have multiplied. He likewise took on board poultry, and other creatures, and garden seeds. At this place the admiral delivered sealed instructions to all the pilots of the fleet, directing them how to shape their course for the territory of Guacanagari in the island of Hispaniola; but these were on no account to be opened, unless in case of separation from him, as he wished as much as possible to prevent the course of the voyage from becoming known to the king of Portugal.
Columbus departed with his fleet from Gomera on Monday the 7th of October, and passing Hierro, the farthest of the Canaries, steered more to the southward than he had done in his first voyage. On the 24th of the same month, having sailed about 450 leagues in his estimation, a swallow was seen among the ships, and they soon afterwards had heavy showers of rain, which the admiral supposed were occasioned by some near land, for which reason he slackened sail at night, and ordered every one to keep a sharp look-out. On Sunday the 3d November, all the fleet saw land to the great joy of all on board. This proved to be an island, which Columbus named Dominica, because discovered on Sunday. Presently two other islands were seen on the starboard, and then many others; and they began to smell the herbs and flowers, and to see flocks of parrots, which always make a great noise during their flight. As there seemed no convenient anchorage on the east coast of Dominica, the admiral continued his course to the second island, which he named Marigalante, that being the name of his own ship. He landed here with some men, and took formal possession in presence of a notary and witnesses. Leaving this island, he discovered another next day, to which he gave the name of Guadaloupe, to which he sent some boats on shore to a small town, which was found deserted by the inhabitants, who had all fled to the mountains. In searching their houses, a piece of ship timber which the sailors call a stern-post was found, to the great surprise of every one, not knowing how it should have come hither, unless either drifted from the Canaries, or perhaps it might have belonged to the admirals ship, lost in the first voyage, and might have floated with the currents from Hispaniola. In this island the Spaniards took the first of those parrots which are called Guacamayas, which are as large as dunghill cocks. Some men went on shore again on Tuesday the 5th of November, who took two youths, who made them understand that they belonged to the island of Borriquen, since named St Juan de Porto Rico, and that the inhabitants of Guadaloupe were Caribbees, and kept them to eat, being canibals. The boats returned for some Spaniards who had remained on shore, and found with them six women who had fled from the Caribbees; but the admiral gave them some hawks-bells and set them on shore. The Caribbees took all from them; and when the boats went again on shore, these women, with a youth and two boys, solicited to be taken on board the ships. From these people it was learnt that there was a continent not far distant, and many islands to which they gave names. On being asked for the island of Ayti, which is the Indian name of Hispaniola, they pointed in the direction where it lay.
The admiral proposed to continue the voyage, but was told that the inspector James Marquй had gone on shore with eight soldiers, at which conduct he was much offended. Parties of men were sent out in different directions, but could not find him, on account of the thickness of the woods. Other parties were again sent on shore, who fired muskets and sounded trumpets, yet all to no purpose, and Columbus was inclined to leave Marquй to his fate, being much concerned at the delay. Yet lest these men might perish, he ordered the ships to take in wood and water, and sent Alonso de Ojeda, who commanded one of the caravels, with forty men, to view the country, and to search for Marquй and his party. Ojeda returned without any tidings of the stragglers, and reported that in travelling six leagues he had waded through twenty-six rivers, many of which took his men to the middle. In this excursion much cotton was seen, and a vast variety of birds in the woods. At length, on Friday the 8th November, the inspector and his men returned, excusing himself that he had lost his way in the prodigiously thick woods, and was unable to get back sooner: But the admiral ordered him to be put under arrest for going on shore without leave. In some of the houses at this island, cotton was found both raw and spun, and likewise a strange sort of looms in which it was wove by the natives. The houses were well constructed, and better stored with provisions than those in the islands which were discovered in the first voyage: But they found abundance of human heads, hung up in the houses, and many baskets full of human bones, from which it was concluded that the natives were canibals, or fed on human flesh.
On the 10th November he coasted along the island of Guadaloupe, towards the north-west, steering for Hispaniola, and discovered a very high island, which he called Montserrate, because it resembled the rocks of that place. He next found a very round island, everywhere perpendicular, so that it seemed impossible to get upon it without the assistance of ladders, and which he named Santa Maria la Redonda, or the round island of St Mary. To another island he gave the name of Santa Maria et Antigua or ancient St Mary, the coast of which extended fifteen or twenty leagues. Many other islands were seen to the northward, which were very high, and covered with woods. He anchored at one of these which he named St Martin; and at another on the 14th November, which he named Santa Cruz, or the Holy Cross. They took four women and two children at this island; and as the boat was returning from the shore, a canoe was met in which there were four men and a woman, who stood on their guard. The woman shot arrows as well as the men, and one of her arrows pierced through a buckler. In boarding, the canoe was overset, and one of the Indians discharged his bow very vigorously while swimming. Holding on their course, so many islands were seen close together that they could not be numbered, or separately named. The admiral called the largest of these the island of St Ursula, and the rest the Eleven thousand Virgins. He came afterwards to another large island, called Borriquen by the natives, but which he named the island of St John the Baptist. It is now called San Juan de Puerto Rico. In a bay on the west coast of this island, the seamen took several kinds of fish in great plenty, such as skate, olaves, pilchards, and some others. On this island many good houses were seen, all of timber and thatched, each having a square inclosure and a clean well beaten path to the shore. The walls of these houses were made of canes woven or wattled together, and they were curiously ornamented with creeping plants or greens, as is usual at Valencia in Spain. Near the sea there was a sort of balcony or open gallery of the same kind of structure, capable to hold twelve persons: But no person was to be seen about the place, all the inhabitants having fled into the interior. On Friday the 22d of November, the first land of Hispaniola was seen on the north side, to which they went straight over from the extreme point of Porto Rico, the two islands being fifteen leagues distant. At this place, which was in the province or district of Samona, the admiral put one of the Indians on shore who had been in Spain, desiring him to tell the natives all the wonderful things he had seen, to induce them to enter into friendship with the Christians. He readily undertook this commission, but was never more heard of, so that he was believed to have died.