Columbus happened upon the island on his first voyage. After discovering Guanahani on October 12, 1492, and vainly searching for Japan among the Bahama Islands, he discovered Cuba and while skirting along the north shore of what he supposed to be the mainland heard of an island said to be rich in gold, lying to the east. Taking an easterly course, he was abandoned by the Pinta, one of his caravels, whose captain, disregarding the admiral's signals, sailed away to seek his fortune alone. Continuing with his remaining caravels, the Santa Maria and the Niña, Columbus reached Cape Maisi, the easternmost point of Cuba, where he sighted a high mountainous land lying in a southeasterly direction. On the following day, December 6, 1492, he reached this land, which he called la Española, because it reminded him of Andalusia. In English histories the name is modified to Hispaniola. The port Columbus called San Nicolas, as he had entered it on St. Nicholas day, and it is now known as Mole St. Nicolas.

Columbus then sailed along the north coast of the island and entered the pretty little port known to-day as Port-à-l'Ecu. Here, on December 12, he solemnly took possession of the country in the name of his sovereigns, erecting a wooden cross on a high hill on the western side of the bay. He then visited Tortuga Island, to the north, giving it this name on account of its shape and the great number of turtles in the water near its coast. After stopping in a harbor which he called Puerto de Paz, Port of Peace, because of the harmony which prevailed at the meetings with the natives, Columbus continued in an easterly direction, but adverse winds compelled him to put into the bay of Santo Tomas, to-day bay of l'Acul, where the cordial intercourse with the natives was renewed. Here he received an embassy from the chief of the district, Guacanagari, inviting him to visit the cacique's residence, further along the coast, and bringing him as presents a wampum belt artistically worked and a wooden mask with eyes, tongue and nose of gold.

To accept the invitation Columbus set sail on the morning of December 24. In the evening when the admiral had retired the helmsman committed the indiscretion of confiding the helm to a ship's boy. About midnight when off Cape Haitien, near their destination, the vessel was caught in a current and swept upon a sandbank where she began to keel over. During the confusion which followed, Columbus had the mainmast chopped down but all efforts to right the ship were in vain, and Columbus and the crew were obliged to take refuge on the little Niña.

As soon as Guacanagari received news of the disaster he sent large canoes filled with men to help the strangers transport their stores to the shore. The relations between the Spaniards and the Indians became most cordial, especially as the Spaniards were gratified to obtain much gold in exchange for articles of insignificant value, owing to which circumstances and to the natural advantages of the location, Columbus determined to build a fort with the wreckage of his vessel. The fort was on a hill east of the site of the present town of Cape Haitien. Columbus gave it the name of La Navidad because he had entered the bay on Christmas day, and leaving thirty-nine men as colonists set out on the Niña on January 4, 1493, on his return trip to Spain.

Near the great yellow promontory on the north of the island, to which Columbus gave the name it still retains of Monte Cristi, the Pinta, which had deserted the other vessels off Cuba, was sighted. Columbus having heard the excuses of the Pinta's captain, took no action with respect to the latter's delinquency, but set about exploring a large river in the vicinity to which he gave the name of Rio de Oro and which to-day is called the Yaque. Continuing the journey along the coast of the island the vessels rounded the giant promontory of Cape Cabron and that of Samana and entered the great bay of Samana which Columbus at first took to be an arm of the sea. Here it was that the first armed encounter between sons of the old world and the new took place. The Indians set upon the Spaniards when they landed but were quickly driven to flight, one of their number being severely wounded. On the following day, however, a more pleasant meeting took place and presents were exchanged. On January 16 the two vessels set sail for Spain.

The immense excitement produced in Spain by the discoveries of Columbus made the preparation of another expedition an easy matter, and on September 25, 1493, the admiral again set out from Spain, this time with sixteen ships and some 1300 men. After touching at several of the Leeward Islands and Porto Rico, the fleet sighted the Samana peninsula on November 22, 1493, and three days later arrived at Monte Cristi. Here the finding of two corpses of Spaniards filled the members of the expedition with grave apprehensions, which proved justified when two days later they arrived at La Navidad and found the fort completely destroyed, the Indian village burnt to the ground, and the whole neighborhood silent and desolate.

Guacanagari was found at a village further inland and according to his story and that of other Indians, a number of Spaniards had succumbed to disease, others were killed in brawls among themselves and the remainder died at the hands of the inland caciques Caonabo and Guarionex and their warriors, who attacked and destroyed both the fort and the village of Guacanagari. At the same time it was stated that the Spaniards had made themselves hateful to the natives by their domineering disposition and their lewdness and covetousness. The finding in some of the native huts of objects that had belonged to the colonists, as well as other suspicious circumstances, caused Father Boil and other companions of Columbus to doubt the chief's story and insist that sanguinary vengeance be taken. Columbus, however, affected to be satisfied with the explanation given and determined to take no further action, but to seek a new location for the colony. From this time forward discord divided not only the Spaniards and Indians but also the Spaniards themselves.

As the fleet was sailing east the weather obliged it to put into an indentation of the coast fifty miles east of Monte Cristi. The place so charmed the Spaniards that it was decided to found a town here. The first city of the new world was therefore laid out and Columbus gave it the name of Isabela, in honor of his royal patron. During the construction of the city Columbus sent two expeditions to the Cibao mountains, both of which succeeded in collecting a large amount of gold.

It soon became evident that the neighborhood of Isabela was not a healthy one. Fever invaded the colony; Columbus himself was not exempt. Discontent came and an uprising among the soldiers was nipped in the bud. On recovering from his illness Columbus resolved to make an exploration of the interior; and with drums beating and flags flying a brilliant expedition left Isabela. The beautiful Royal Plain was soon reached and friendly relations established with its peaceful inhabitants, whose wonder at the Spaniards and terror at their horses knew no bounds. A fortress was founded on the banks of the Janico river and called Santo Tomas. Columbus then returned to Isabela to find the town in a state of excitement on account of petty quarrels and the general sickness. Picking out the principal malcontents he sent them to Santo Tomas, and ordered that another fortress be founded. On April 24, 1494, he left the island with three vessels for a voyage of exploration to the west, entrusting the government of the colony to his brother Diego and an executive council.

But a short time elapsed before new dissensions broke out, followed by troubles with the Indians. A military expedition dispatched to the interior committed numerous depredations and drove the natives into the ranks of Caonabo, who was planning the expulsion of the strangers. The commander of the expedition, Moisen Pedro de Margarite, was called to account by Diego Columbus; but conspiring with Father Boil, the religious head of the colony, the two contrived to excite a popular insurrection against the governor, which may be regarded as the first Dominican revolution. At this time Bartholomew Columbus, another brother of the admiral, arrived with provisions, and the insurrectionists, taking possession of the ships, returned in them to Spain where they lost no opportunity to disparage the achievements of Columbus and to slander him and his brothers.