Being now certain that he could get no passage to the westwards, the admiral stood back that same day to the east, designing to pass the Boca del Drago, or that strait which he had seen between Trinidada and the land called Paria by the Indians. In this strait there are four small islands to the east, next that point of Trindada which he named Cabo de Boca, or Cape Mouth, because it was blunt; and the western cape upon the continent he called Cabo de Lapa. The reason why he gave this strait the name of the Dragons Mouth, was because it was very dangerous, on account of the prodigious quantity of fresh water which continually struggles to get out that way into the open sea, and that the strait is divided into three boisterous channels by intervening islands. While sailing through this strait the wind failed, and he was in great danger of being drifted by the raging current against some sand or rock; he gave it this name likewise as corresponding with that he had before given to the other entrance into the gulf of Paria, the Boca del Sierpe or Serpents Mouth, where he was in no less danger. But it pleased God, that what they most dreaded should prove their greatest safety, for the strength of the current carried them clear through. On Monday the 17th of August, he began to sail westwards along the northern coast of Paria, in order to stand over afterwards for Hispaniola, and gave thanks to God who had delivered from so many troubles and dangers, still shewing him new countries full of peaceable people, and abounding in wealth, more especially that which he now certainly concluded to be the continent, because of the great extent of the gulf of Pearls and the size of the rivers that run into it, making it all deep water, and all the Indians of the Caribbean islands had told him there was a vast land to the southward. Likewise, according to the authority of Esdras, the 8th chapter of the 4th book, if the world were divided into seven equal parts, one only is water and the rest land.

Sailing along to the westwards on the coast of Paria, the admiral fell gradually off from it towards the N.W. being so drifted by the current owing to the calmness of the weather, so that on Wednesday the 15th of August, he left the Cabo de las Conchas, or Cape of Shells to the south, and the island of Margarita to the west, which name, signifying the isle of Pearls, he gave to it as by divine inspiration, as close to it is the isle of Cabagua where an infinite quantity of pearls have since been found; and he afterwards named some mountains in Hispaniola and Jamaica the Gold Mountains, where the greatest quantity and largest pieces of that metal that were ever carried into Spain were afterwards found. But to return to his voyage, he held on his way by six islands which he called de las Guardas, or the Guards, and three others more to the north called los Testigos, or the Witnesses. Though they still discovered much land in Paria to the westwards, yet the admiral says in his journal that he could not from this time give such an account of it as he wished, because through much watching his eyes were inflamed, and he was therefore forced to take most of his observations from the sailors and pilots. This same night, the sixteenth of August, the compasses, which hitherto had not varied, did now at least a point and a half, and some of them two points, and in this there could be no mistake, as several persons had attentively observed the circumstance. The admiral admired much at this, and was much grieved that he had not an opportunity of following the coast of the continent any farther; he therefore held on his course to the N.W. till on Monday the twentieth of August, he came to an anchor between Isla Beata or the Blessed Island and Hispaniola, whence he sent a letter overland to his brother the Adelantado, acquainting him with his safe arrival and his success in having discovered the continent. The admiral was much surprised at finding himself so far to the westwards, for although he was aware of the power of the currents, he did not expect they would have produced so great an effect. Therefore, that his provisions might not fail, he stood to the eastwards for San Domingo, into which harbour he sailed on the thirtieth of August. Here the lieutenant his brother had appointed to build a city, on the east side of the river where it now stands, and which, in memory of his father, named Domingo or Dominick, is now named Santo Domingo.

On his arrival at St Domingo, the admiral was almost blind with overwatching and fatigue, and hoped there to rest himself and to find peace among the people of the colony; but he found quite the contrary, for all the people of the island were in disorder and rebellion. Great numbers of those whom he had left were dead, and of those who remained above 160 individuals were ill of the French pox; besides that many were in rebellion, with Francis Roldan at their head, whom he had left as alcalde mayor, or chief justice of the island. And to add to the evil, the three ships that he had dispatched from the Canary islands with supplies had not yet arrived. Of all these matters it is requisite that we should treat in an orderly manner, beginning from the time when the admiral had set out from this island for Spain in March 1496, thirty months before his present return.

For some considerable time after his departure, matters went on pretty quietly in hopes of his speedy return and receiving supplies and relief. But after the first year, finding their hopes abortive, the Spanish provisions having utterly failed, and sickness and sufferings increasing, the people began to be much dissatisfied with their situation, and to despair of any change for the better. When any discontented persons begin to utter complaints, they are always sure to find some bold spirit to urge them on, desirous to become the head of a party: Such on this occasion was the conduct of Francis Roldan, a native of Torre de Ximena, whom the admiral had left in great power both among the Christians and Indians, by making him chief judge of the colony, so that he had almost as much power and authority as himself. For this reason it is supposed that there was not that good understanding between him and the admirals lieutenant as ought to have been for the public good, as appeared actually to have been the case in the sequel. And, as the admiral neither returned himself nor sent any supplies, this Roldan began to entertain schemes of usurping the supreme authority in the island, and designed for this purpose to murder the admirals brothers as those who were best able to oppose his rebellion, and actually waited an opportunity of putting this nefarious intention into execution. It happened that the lieutenant went to a province in the west called Xaragua, eighty leagues from Isabella, leaving Roldan in the execution of his employment, but subordinate to Don James the admirals second brother. Roldan was so much offended at this procedure, that while the lieutenant was taking order how the caciques should pay their quotas of the tribute to their Catholic majesties after the rate which had been settled by the admiral, Roldan began underhand to draw over some of the malcontents to his party. But that it might not prove fatal to rise too suddenly and without some colourable pretence, Roldan took hold of the following circumstance to favour his covert practices. The lieutenant had caused a caravel to be built at Isabella, to have ready to send to Spain in case of any urgent necessity, and for want of tackle and other necessary equipments it still lay upon the bench unlaunched. Roldan insinuated that the delay in launching this vessel was occasioned by other reasons, and that it was necessary for the common benefit that it should be fitted out, that some persons might be sent into Spain to represent their sufferings and to implore relief. Thus under pretence of the public good, Roldan pressed that the caravel might be launched, and as Don James Columbus refused his consent on account of the want of tackle, Roldan began more boldly to treat with some of the malcontents about launching the caravel in spite of his refusal; telling those whom he thought would fall into his measures, that the reason why the lieutenant and his brother were averse to this measure was, that they were desirous to secure the dominion of the island to themselves and to keep them in subjection, and that there might not be any vessel to carry news of their revolt to their Catholic majesties. And since they were sensible of the cruelty and ill nature of the lieutenant, and the restless and laborious life he led them, in continually building towns and forts without necessity, and as there were now no hopes of the admiral returning with supplies, it was fit they should seize upon that caravel to procure their own liberty and relief, and not suffer themselves, under pretence of pay which they never received, to be kept under the authority of a foreigner, when it was in their power to live in ease and plenty. That by assuming the authority into their own hands, they would have it in their power to divide the island equally amongst them, and would be served by the Indians to their own content; whereas the lieutenant now hold them under such rigorous authority that they could not take to wife any Indian woman they pleased, and were forced to keep the three vows of monachism, chastity, poverty, and abstinence, and were not wanting in fasts and penances, imprisonments, and other punishments, which were liberally bestowed for the smallest offences. Wherefore, since he Roldan held the rod of justice and royal authority, and could screen them against evil consequences on this account, he advised them to act as he directed, in doing which they could not be found guilty. With such pretences and arguments, proceeding from the hatred he bore to the lieutenant, he drew over so many to his party, that one day, after the return of the lieutenant from Xaragua to Isabella, some of the conspirators resolved to stab him, and considered this as so easy a matter that they had provided a halter to hang him up with after his death. The circumstance which more immediately incensed them at this particular period, was the imprisonment of one Barahoria, a friend to the conspirators; and if God had not put it into the heart of the lieutenant not to proceed to the execution of justice at this time against that person, the conspirators had then certainly murdered him.