The mood aboard all three ships was dour as Columbus noted in his log as early as September 24, 'the more God shows the men manifest signs that we are near land, the more their impatience and inconstancy increases.' Fearful of losing his life at the hands of a crew loyal to Pinzón and his brothers, Columbus expressed his concern in the ship's log: 'I know Under Columbus's orders, the three ships maintained a course westward, but on October 7 Pinzón convinced the commander to alter their direction to southwest, where he remained convinced they would find land. In the ship's log for September 18, 1492, Columbus describes the captain of the Pinta as 'very resourceful, but his independence disturbs me somewhat.' Pinzón had sailed some distance ahead of Columbus for the greater part of two days-'I trust that this tendency to strike out on his own does not continue, for we can ill afford to become separated this far from home.' By mid-September Pinzón was actively encouraging Columbus to turn to the north, a move he decided was prudent based upon the rough maps they were sailing by. On September 6, the squadron again weighed anchor and set their course due west. Together with its two companion ships, the Pinta made for the Canary Islands but, three days out of Palos, dropped its rudder and was forced to limp along with a makeshift device until the 15th, when Pinzón arrived at the Canary Islands to do the necessary repairs. The Pinta was a three-masted, square rigger 70 feet in length, with a mast rising 26 feet in the air and a draft-the depth of water a loaded ship requires in order to float-of less than eight feet. The Niña and the Pinta were caravels: lighter, faster, and more maneuverable that the squadron flagship. Forty crewmen served aboard the Santa Maria, which covered a distance of approximately 150 miles in a day.

The largest of the three ships, the cumbersome Santa Maria was a full-rigged ship that weighed about 100 tons and measured approximately 100 feet from stem to stern. Pinzón's younger brother Vicente Yanez Pinzón served as commander of the 24-man crew of the Niña, while yet another brother, Francisco Martin Pinzón, worked under Martín as pilot or first mate. Columbus commanded the flagship, the Santa Maria, while in the smaller Pinta, Pinzón captained his crew of 26 men.

On August 3, 1492, Columbus set sail from Palos, Spain his squadron of three ships contained 120 men. In addition, it was through his efforts that a crew of men with skills and temperament suitable for such an arduous voyage was secured. He also paid the Italian the sum of one-eighth of the anticipated expenses of the trip. Whatever his initial reason or motive, Pinzón became an enthusiastic backer of the voyage and when asked by Queen Isabella's advisors for his opinion regarding the proposed voyage he expressed confidence in Columbus. Curious, he examined charts in the possession of the Vatican that were drawn up by Norman explorers years earlier. Other historians argue that, while in Rome years before, Pinzón learned about a country named Vineland, and realized that there were land masses that had yet to be discovered. According to some sources, he became acquainted with Columbus through Franciscan Father Juan Perez, prior of the convent of La Rábida. Several years before meeting Columbus, Pinzón had retired from active life as a sailor, and set up shop as a shipbuilder. With expenses totaling more than Ferdinand and Isabella were willing to bestow, Columbus solicited additional backers, one of which was 51-year-old Pinzón, who fronted part of the money needed to purchase supplies for the voyage as well as a part-interest in both the Niña and the Pinta. After the Italian, French, and English crown refused to back him, Colón, or Columbus, as he is most widely known, traveled west across the Pyrenees to Spain, and, after much convincing, in April of 1492 gained the patronage of King Ferdinand of Aragon and Queen Isabella of Castile. However, he needed funding for what would likely be a costly and uncertain voyage. In the mid-1470s Italian explorer Cristóbal Colón formulated a plan to reach India and the Orient by sailing around the circumference of the earth in the opposite direction. He also sailed in the Mediterranean and had traveled the Atlantic to the Canary Islands. There he and his crew followed that continent to the southwest, where they discovered the mouth of a large river. In the prime of his career, under Cousin, a navigator from Dieppe, Pinzón sailed to the eastern coast of Africa.

He was the eldest son of a wealthy family of seafarers and shipowners, and he became a strong, capable sailor and skillful pilot himself. Pinzón was born in 1441 in Palos de Moguer, a seaport town in the Spanish province of Andalusia.

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