On Wednesday the 16th of January 1493, the admiral set sail from the Gulf of Arrows, or Samana, with a fair wind for Spain, both caravels being now very leaky and requiring much labour at the pumps to keep them right. Cape Santelmo was the last land they saw; twenty leagues north-east of it there appeared great abundance of weeds, and twenty leagues still farther on the whole sea was covered with multitudes of small tunny fishes, and they saw great numbers of them on the two following days, the 19th and 20th of January, followed by great flocks of sea-fowl; and all the weeds ran with the currents in long ropes east and west; for they always found that the current takes these weeds a great way out to sea, and that they do not continue long in the same direction, as they sometimes go one way, and sometimes another, as carried by the changes of the currents; and these weeds continued to accompany them for many days, until they were almost half way across the Atlantic.
Holding on their course steadily with a fair wind, they made such way, that on the 9th of February, the pilots believed they had got to the south of the Azores; but in the opinion of the admiral, they were still 150 leagues to the west of these islands, and his reckoning turned out to be true. They still found abundance of weeds, which, when they formerly sailed to the West Indies, had not been seen until they were 263 leagues west from the island of Ferro. As they sailed thus onwards with fair weather and favourable winds, the wind began to rise, and increased from day to day with a high sea, till at length they could hardly live upon it. The storm had so increased on Thursday the 14th of February, that they could no longer carry sail, and had to drive whichever way the wind blew; but the Pinta, unable to lie athwart the sea, bore away due north before the wind, which now came from the south; and though the admiral always carried a light, she was entirely out of sight next morning. Considering their consort to be certainly lost, and believing themselves in imminent hazard, the whole company betook themselves to prayers, and cast lots which of them should go on pilgrimage for the whole crew to the shrine of our Lady of Guadaloupe, which fell upon the admiral. They afterwards drew for another to go to Loretto, and the lot fell upon Peter de Villa, a seaman of Port St Mary; and they cast lots for a third to watch all night at the shrine of St Olave of Moguer. The storm still increasing, they all made a vow to go barefooted, and in their shirts, to some church of our Lady at the first land they might come to. Besides these general vows, several others were made by individuals. The tempest was now very violent, and the admirals ship could hardly withstand its fury for want of ballast, which was fallen very short in consequence of the provisions and water being mostly expended. To supply this want, they filled all the empty casks in the ship with sea water, which was some help and made the ship to bear more upright, and be in less danger of oversetting. Of this violent storm the admiral wrote thus to their Catholic majesties:
"I had been less concerned at the tempest had I alone been in danger, for I know that I owe my life to my Creator, and I have often been so near death that only the slightest circumstance was wanting to its completion. But, since it had pleased God to give me faith and assurance to go upon this my undertaking in which I have been completely successful, I was exceedingly distressed lest the fruits of my discoveries might be lost to your highnesses by my death; whereas if I survived, those who opposed my proposal would be convinced, and your highnesses served by me with honour and increase of your royal state. I was therefore much grieved and troubled lest the Divine Majesty should please to obstruct all this by my death, which had yet been more tolerable to contemplate if it were not attended with the loss of all those men I had carried with me upon promise of happy success. They, seeing themselves in so great jeopardy, did not only curse their setting out upon the expedition, but the fear and awe which I had impressed upon them, to dissuade them from returning when outward bound, as they had several times resolved upon. Above all, my sorrow was redoubled by the remembrance of two sons whom I had left at school in Cordova, destitute of friends and in a strange country, before I had done, or at least before it could be known that I had performed any service which might incline your majesties to remember and protect them."
"Though I comforted myself with the hope that God would not allow a matter which tended so much to the exaltation of his church to be left imperfect, when I had through so much opposition and trouble brought it almost to perfection; yet I considered that it might be his will that I should not be permitted to obtain such honour in this world, because of my demerits. In this perplexity, I remembered your highnesses good fortune; which, though I were dead and the ship lost, might yet find some means that a conquest so nearly achieved should not be lost, and that possibly the success of my voyage might come to your knowledge by some means or other. With this view, as briefly as the time would permit, I wrote upon parchment that I had discovered the lands which I had promised; likewise how many days were employed on the voyage, the direction in which I had sailed, the goodness of the country, the nature of the inhabitants, and how some of your highnesses subjects were left in possession of my discoveries. Which writing I folded and sealed up and superscribed to your highnesses, promising a reward of 1000 ducats to whoever might deliver it sealed into your hands; that, in case it might be found by a foreigner, the promised reward might induce him not to communicate the intelligence. I then caused a great cask to be brought to me, and having wrapped the writing in oiled cloth, which I surrounded with a cake of wax, I placed the whole in the cask: I then carefully closed up the bung-hole and threw the cask into the sea, all the people fancying that it was some act of devotion. Apprehending that this might never be taken up, and the ship coming still nearer to Spain, I made another packet like the first, which I placed on the poop, that when the ship sunk the cask might float upon the water, and take its chance of being found."
Sailing on in such extreme danger, at break of day on Friday the 15th of February, one Ruy Garcia saw land from the round top bearing E.N.E. The pilot and seamen judged it might be the rock of Lisbon, but the admiral concluded that it was one of the Azores. Yet though at no great distance, they could not come to anchor there that day because of the weather, and the wind being easterly, they lost sight of that island, and got sight of another, towards which they used every effort to approach, struggling with continual labour against wind and weather, but unable to reach the land. In his journal, the admiral says that on the night of Saturday the 16th of February he arrived at one of the Azores, but could not tell which; and having had no rest from the foregoing Wednesday, and being lame in both legs by being continually wet and in the open air, he took some sleep that night. Even provisions were now scanty. Having come to anchor on Monday the 18th February, he learnt from some of the inhabitants that it was the island of St Mary, one of the Azores, and the inhabitants expressed great surprize that the ship had weathered the storm, which had continued fifteen days in these parts without intermission.
Learning the great discovery which the admiral had made, the inhabitants of St Mary seemed greatly to rejoice, giving praise to God, and three of them came on board with some fresh provisions, and with many compliments from the commander of the island, who resided at the town not far from thence. About this place nothing was seen but a hermitage, said to be dedicated to the Blessed virgin; whereupon the admiral and all the crew, bearing in remembrance the vow which they had made on the Thursday before, to go barefooted and in their shirts to some church of our Lady at the first land, were of opinion that they ought here to discharge their vow, especially as the governor and people expressed so much kindness for them, and as they belonged to a king who was in perfect amity with Castile. The admiral therefore requested these three men to repair to the town and cause a chaplain to come to the hermitage to say mass for them. To this these men consented, and went on shore in the caravels boat with half the crew, that they might perform their vow, meaning on their return that the other half of the ships company should then go on shore in their turn. They accordingly landed, and proceeded according to their vow barefooted and in their shirts towards the hermitage; but the governor and many people from the town, who lay in ambush, suddenly rushed out upon them and made them all prisoners, taking away their boat at the same time, without which they believed it impossible for the admiral to get away from thence.