Leaving that place, the winds and torrents of rain seem to have conspired to obstruct his progress; and at one time a water spout fell upon the deck of his ship, so that it appeared a miraculous interposition of Providence which enabled them to lower the sails, and let go the anchors. So much water was shipped at this time, that it required the utmost exertions of the crew at the pumps to free the ship. In addition to all their distresses, the people were now reduced to a pound of rotten biscuit, and half a pint of wine a-day for each man, having no other provisions, unless when they happened to take some fish. Under all these difficulties, the admiral arrived on the 18th of July at Cape Cruz, where he remained three days, as the Indians supplied the people liberally with fruit and provisions. On Tuesday the 22d of July, as the wind was still adverse for his return to Isabella in the island of Hispaniola, he struck over to the island of Jamaica, which he named Sant Jago. He coasted along this island to the westwards, admiring its delightful appearance and numerous harbours. Great numbers of Indians followed the ships along the coast, and freely parted with such provisions as the country afforded, which the Spaniards thought better than they had met with in any of the other islands. But he never failed to have heavy rains every evening, which he endeavoured to account for by the proximity of such extensive woods. At one place he saw a very beautiful bay, having seven small islands, one of which was extraordinary high land. The admiral thought this island very large and beautiful, and to have an unusual number of towns; but it afterwards turned out to be Jamaica itself, which is eighty leagues long and fifty broad131.

The weather becoming more settled, the admiral stood to the eastwards for Hispaniola, and came to the extreme point of that island stretching towards Jamaica, which he called Cabo de Ferol, or Cape Lighthouse132; and on Wednesday the 20th of August, he got sight of the westernmost point of Hispaniola, which he named Cape St Michael, now called Tiberoon; which is twenty-five or thirty leagues from the easternmost point of Jamaica133. On, Saturday the 23d of August, a cacique came off to the ships, calling out Almirante! Almirante! from which circumstance he inferred that he had fallen in with Hispaniola, of which he was not till then assured. At the end of August, he anchored at a small island which looks like a sail, which he therefore named Alto Vela, being twelve leagues from Beata134. The other two ships being out of sight, the admiral sent some of his men to the top of this island to look out for them. While on shore the seamen killed five seals which lay asleep on the sand, and knocked down many birds with their sticks, even catching some with their hands, for a the island was uninhabited they were not afraid of men. After six days waiting, the other ships rejoined the admiral; and he proceeded to La Beata, and thence eastwards along the coast of Hispaniola to a river running through a fine populous plain, now called Catalina, or Catherines Plain, from the name of a lady to whom it once belonged135. Some Indians came off to the ships in their canoes, who said the Spaniards from the town of Isabella had been there, and were all well. Going on eastwards from this place, a large town was observed on shore, to which he sent the boats for water. The Indians came out armed with poisoned arrows, and threatened to bind the Spaniards with cords; yet as soon as the boats came near, they laid down their arms, inquired for the admiral, and brought provisions to the Spaniards. This place is in the province of Higuay, the natives of which are the most warlike of all the tribes in Hispaniola, and use poisoned arrows.

Continuing the course to the eastwards, a large fish was seen resembling a small whale, having a shell on its neck like that of a tortoise, as large as a target. Its head, which it held above water, was like a pipe or large cask; it had two vast fins on the sides, and the tail resembled that of a tunny fish, but much larger. From the appearance of this fish, and by other tokens in the sky, the admiral suspected an approaching storm, and took shelter therefore within an island called Adamanoy by the Indians, but which the Spaniards name Saona, which is about two leagues in length, having a strait between it and Hispaniola about a league in breadth. He there anchored, but as the other two ships were unable to get in they ran great danger. That night, the admiral observed an eclipse of the moon, from which he calculated the difference of longitude between the island of Saona and Cadiz to be five hours and twenty-three minutes136. The admiral remained in this place for eight days, and being rejoined by the other ships, he made sail on the 24th September, and arrived at Cabo de Ergario137, or Cape Deceit, which he named San Raphael. He then touched at the island of Mona, ten leagues from Hispaniola, and eight from San Joan de Porto Rico. Leaving Mona, where the Spaniards got most delicious melons as large as a two gallon vessel, the admiral was siezed by a violent lethargy in which he lost his senses, and every one expected him to die. In this emergency, the other officers made the best of their way for Isabella, where all the ships arrived on the 29th of September, without having been able to ascertain whether or not Cuba was an island, except from the information of an Indian, as already mentioned.

On his arrival at Isabella, the admiral had the satisfaction to learn that his brother Don Bartholomew Columbus was there, but this pleasing intelligence was much damped by information that the natives of the island had risen in arms against the Spaniards. Don Bartholomew had gone to England to offer the proposed discovery of the Indies to King Henry VII. He was long delayed on his way there, and spent a long time in learning the language, and in soliciting at court before he could gain admission to the ministry; insomuch, that seven years had elapsed from his leaving Spain before his negociations were finished with King Henry, who agreed to the proposed terms, and entered into articles with him for the employment of the admiral. He then set out on his return to Spain in search of his brother, who not having heard of him for so long a time, concluded that he had died. When at Paris, he learnt that his brother had actually made the discovery, and was already appointed admiral of the Indies. Charles, the headstrong, who then reigned in France, gave him 100 crowns to assist his journey into Spain; but his brother was already sailed on his second voyage before his arrival. He found, however, the instructions which the admiral had left for him, and went in consequence to court to visit his nephews, who were pages to Prince John. Their Catholic majesties received him very graciously, and gave him the command of three ships, to carry out a supply of provisions to the new colony, where he had arrived in April, after the admiral had sailed to explore Cuba. Don Bartholomew was a discreet man, as skilful in sea affairs as his brother, and had many commendable qualities; he was besides very brave and resolute but of a blunt manner, and somewhat harsh in his temper, by which he incurred the hatred of some persons of the colony. As the admiral hoped to derive much assistance from Don Bartholomew, he gave him the title of adelantado, or lieutenant-governor of the Indies; at which their Catholic majesties were offended, considering that the admiral had exceeded his powers in giving this appointment, which ought only to have come from them; yet they confirmed it some years afterwards.