The vessels being ready for sea, were supplied with provisions for one year, and took on board a complement of ninety men, most of whom were inhabitants of Palos, except some friends of Columbus, and a few servants of the court. They set sail half an hour before sun-rise on the 3d of August 1492, going over the bar of the river Saltes, on which Palos is situated, and directing their course for the Canaries; the whole crews of all the three vessels, after the example of Columbus, having previously made confession of their sins, and partaken of the holy sacrament. On the very next day, the rudder of the caravel Pinta, which Martin Alonso Pinzon commanded, broke loose; which was suspected to have happened by the contrivance of Gomez Rascon and Christopher Quintero, her owners, and serving as seamen on board, because they went on the voyage against their inclination, and had endeavoured to throw obstacles in its way before setting out. This obliged the Pinto to lie to, and the admiral made up to the caravel, though he could not give any aid, on purpose to encourage the men. Martin Alonso Pinzon being an experienced seaman, soon fastened the rudder in such a manner with ropes as enabled her to continue the voyage: But on the Tuesday following, it broke loose again through the violence of the waves, and the whole of the small squadron was forced to lie to. This early misfortune might have discouraged a superstitious person, more especially considering the refractory conduct of M.A. Pinzon afterwards. The rudder was again made fast as well as they could; and, continuing their voyage, they discovered the Canaries about day-break of the 11th of August. After endeavouring for two days to reach Gran Canaria, and always baffled by contrary winds, Martin Alonso was left with orders to proceed to land as soon as he could, to endeavour to procure another ship, and the admiral went with the other two to Gomera with the same view. Not finding any vessel for his purpose, he returned to Gran Canaria, where he got a new rudder for the Pinta, and had her sails changed from latine or triangular, into square, that she might labour less, and be able more safely to keep up with the others. Leaving Gran Canaria on the afternoon of the 1st September, he returned to Gomera, where he took in a supply of flesh, and wood and water, with great haste in the course of four days; as he had heard of some Portuguese caravels cruising in those parts to intercept him, the king of Portugal being much concerned to learn that Columbus had agreed with their Catholic majesties, by which he had missed the opportunity of aggrandizing his own crown.

On Thursday the 6th of September, Columbus took his final departure from Gomera, standing to the westwards in quest of his proposed discovery, and made but little way for want of wind: Yet they lost sight of land next day, when many bewailed their state with sighs and tears, believing they were never more to see land; but Columbus did all in his power to raise their hopes, by the promise of success, and of acquiring wealth. That day they ran eighteen leagues, while the admiral gave out they had only advanced fifteen; thinking it prudent to reckon the voyage short, on purpose to lessen the apprehensions of the seamen. On the 11th of September, being 150 leagues to the westwards of Ferro, they saw a mast floating on the sea, that seemed to have been drifted by the current, which a little farther on, they found setting very rapidly to the northwards. On the 14th September, being 50 leagues more to the west, the admiral, about night-fall, perceived the needle to vary a point westwards, and somewhat more early next morning. This variation had never been observed before, and therefore astonished the admiral greatly; and still more so, three days after, when he had advanced 100 leagues farther to the westwards, on finding the needle to vary two points in the evening, and to point directly north next morning. On the night of Saturday the 15th September, being then near 300 leagues west from Ferro, they saw a flame of fire drop into the sea, four or five leagues S.W. from the ships, the weather being then calm, the sea smooth, and the current setting to the N.E. The people in the Ninna said they had seen some water-wagtails on the day before, at which they much admired, considering that these birds never go above fifteen or twenty leagues from land. On the next day, they were still more surprised at seeing some spots of green and yellow weeds on the surface of the sea, which seemed newly broken off from some island or rock. On Monday the 17th, they saw much more, and many concluded they were near land, more especially as a live grasshopper was seen on the weeds. Others of the companies alleged these weeds might come from banks or rocks under water, and the people, beginning to be afraid, muttered against the prosecution of the voyage. They now perceived that the water was not more than half as salt as usual, and that night they saw many tunny fishes, which followed so near the ships that a man belonging to the Ninna killed one with a harpoon. In the morning the air was temperate and delightful, like the April weather of Andalusia. When about 360 leagues westwards of Ferro, another water-wagtail was seen; and on Tuesday the 18th September, Martin Alonso Pinzon, being before in the Pinta which was an excellent sailer, lay to for the admiral, and reported that he had seen a numerous flock of birds flying westwards, from which he had hopes of discovering land that night, at about fifteen leagues to the northwards, and even fancied he had seen it: But the admiral did not credit this, and would not lose time by deviating from his course in search of the supposed land, though all the people were much inclined to have made the attempt. That night the wind freshened, when they had sailed eleven days always before the wind to the west, without ever having to handle a sail. During the whole course, the admiral constantly noted down every circumstance; as the winds, the fishes, birds, and other tokens of land, and continually kept a good look out, frequently trying for soundings.

Being altogether unacquainted with the voyage, and seeing nothing but sky and water for so many days, the people began to mutter among themselves, as thinking their situation desperate, and anxiously looked out for signs of land, no one having ever been so far out at sea as they then were. On Wednesday 19th September, a sea gull came on board the admiral, and others appeared in the evening; which raised their hopes of land, believing these birds did not fly far out to sea. Throwing the lead with a line of 200 fathoms, no ground was found, but the current was found setting to the S.W. On Thursday the 20th two more gulls were seen; some time after they took a black bird, having a white spot on its crown and feet like a duck; they killed a small fish, and sailed over large quantities of weeds. From all which tokens the people began to pluck up fresh courage. Next morning, three small land birds settled on the rigging of the admiral, where they continued singing till the sun rose, when they flew away. This strengthened their hopes of land; as, though the other birds might venture out to sea, those small birds could not as they thought, go far from land. Some time after, a gull was seen flying from W.N.W. next afternoon a water-wagtail and another gull, and more weeds to the northwards, which encouraged them in the belief that they came from some land not far off. Yet these very weeds troubled them, as they were sometimes in such thick spots as to impede the way of the ships, and they therefore avoided them as much as possible. Next day they saw a whale, and on the 22d September some birds. During three days the winds were from the S.W. which, though contrary, the admiral said were a good sign, because the ships having hitherto sailed always before the wind, the men believed they would never have a fair wind to return with. Notwithstanding every encouragement that the admiral could devise, the men grew mutinous and slighted him, railing against the king for sending them on such a voyage; while he sometimes endeavoured to sooth them with hopes, and at other times threatened them with the punishment they might look for from the king, for their cowardice and disobedience. On the 23d, the wind sprung up at W. N.W. with a rough sea, which pleased every one; at nine in the morning a turtle-dove flew athwart the admiral; in the afternoon a gull and other white birds, and grasshoppers were seen among the weeds. Next day another gull was seen, and turtle-doves came from the westwards; some small fishes also were seen, which were killed with harpoons, as they would not take bait.