Columbus first sailed to the Canary Islands, which belonged to Castile, where he restocked the provisions and made repairs. After stopping over in Gran Canaria, he departed from San Sebastián de La Gomera on 6 September, for what turned out to be a five-week voyage across the ocean. A lookout on the Pinta, Rodrigo de Triana (also known as Juan Rodríguez Bermeo), spotted land about 2:00 on the morning of 12 October, and immediately alerted the rest of the crew with a shout. Thereupon, the captain of the Pinta, Martín Alonso Pinzón, verified the discovery and alerted Columbus by firing a lombard. Columbus later maintained that he himself had already seen a light on the land a few hours earlier, thereby claiming for himself the lifetime pension promised by Ferdinand and Isabella to the first person to sight land.
Christopher Columbus at the gates of the monastery of Santa María de la Rábida with his son Diego, by Benet Mercadé
Columbus called the island (in what is now The Bahamas) San Salvador; the natives called it Guanahani. Exactly which island in the Bahamas this corresponds to is unresolved. Based on primary accounts and based on what one would expect based on the geographic positions of the islands given Columbus's venture's course, the prime candidates are San Salvador Island (so named in 1925 on the theory that it was Columbus's San Salvador), Samana Cay, and Plana Cays.
The indigenous people he encountered, the Lucayan, Taíno, or Arawak, were peaceful and friendly. Noting their gold ear ornaments, Columbus took some of the Arawaks prisoner and insisted that they guide him to the source of the gold.
From the entry in his journal of 12 October 1492, in which he wrote of them, "Many of the men I have seen have scars on their bodies, and when I made signs to them to find out how this happened, they indicated that people from other nearby islands come to San Salvador to capture them; they defend themselves the best they can. I believe that people from the mainland come here to take them as slaves. They ought to make good and skilled servants, for they repeat very quickly whatever we say to them. I think they can very easily be made Christians, for they seem to have no religion. If it pleases our Lord, I will take six of them to Your Highnesses when I depart, in order that they may learn our language."
Columbus remarked that their lack of modern weaponry and metal-forged swords or pikes was a tactical vulnerability, writing, "I could conquer the whole of them with 50 men, and govern them as I pleased."
Columbus's handwritten notes in Latin, on the margins of his copy of The Travels of Marco Polo
Columbus also explored the northeast coast of Cuba, where he landed on 28 October. On 22 November, Martín Alonso Pinzón took the Pinta on an unauthorized expedition in search of an island called "Babeque" or "Baneque", which the natives had told him was rich in gold. Columbus, for his part, continued to the northern coast of Hispaniola, where he landed on 5 December.
There, the Santa María ran aground on Christmas Day 1492 and had to be abandoned. The wreck was used as a target for cannon fire to impress the native peoples. Columbus was received by the native cacique Guacanagari, who gave him permission to leave some of his men behind. Columbus left 39 men, including Luis de Torres, the Converso interpreter, who spoke Hebrew and Arabic, and founded the settlement of La Navidad at the site of present-day Bord de Mer de Limonade, Haiti. Columbus took more natives prisoner and continued his exploration. He kept sailing along the northern coast of Hispaniola with a single ship, until he encountered Pinzón and the Pinta on 6 January.
On 13 January 1493, Columbus made his last stop of this voyage in the New World. He landed on the Bay of Rincón in the northeastern border of the Samaná Peninsula, where he met the warrior-like Cigüayos who presented him with his only violent resistance during his first voyage to the Americas. The Cigüayos had refused to trade the amount of bows and arrows that Columbus desired; in the ensuing violence one was stabbed in the buttocks and another wounded with an arrow on his chest. Because of this and because of the Cigüayos' use of arrows, he called the inlet where he met them the Bay of Arrows (or Gulf of Arrows). Today, the place is called the Bay of Rincón, in Samaná, the Dominican Republic. Columbus kidnapped about 10 to 25 natives and took them back with him (only seven or eight of the natives arrived in Spain alive).
"Columbus map", drawn c. 1490 in the Lisbon workshop of Bartolomeo and Christopher Columbus
Columbus headed for Spain on the Niña, but a storm separated him from the Pinta, and forced the Niña to stop at the island of Santa Maria in the Azores. Half of his crew went ashore to say prayers in a chapel to give thanks for having survived the storm, but while praying, these crew members were imprisoned by the island captain, ostensibly on suspicion of being pirates. After a two-day standoff, the prisoners were released, and Columbus again set sail for Spain. Another storm forced him into the port at Lisbon. He anchored next to the King's harbor patrol ship on 4 March 1493 in Portugal and was interviewed by Bartolomeu Dias, whose rounding of the Cape of Good Hope a few years earlier in 1488–1489 had complicated Columbus's attempts for funding from the Portuguese court.
Not finding King John II of Portugal in Lisbon, Columbus wrote a letter to him and waited for the king's reply. The king requested that Columbus go to Vale do Paraíso north of Lisbon to meet him. Relations between Portugal and Castile were poor at the time. Columbus went to meet with the king at Vale do Paraíso. Hearing of Columbus's discoveries, the Portuguese king informed him that he believed the voyage to be in violation of the 1479 Treaty of Alcáçovas. After spending more than a week in Portugal, and paying his respects to Eleanor of Viseu, he again set sail for Spain. Ferdinand Magellan was a young boy and a ward of Eleanor's court; it is likely he saw Columbus during this visit. After departing, and after reportedly being saved from assassins by John II of Portugal, Columbus crossed the bar of Saltes and entered the harbor of Palos on 15 March 1493. Word of his finding new lands rapidly spread throughout Europe.
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