Though Columbus' first voyage to the Americas is undoubtedly his most famous historically, he didn't reach the island of Jamaica until his second voyage. He had already been to Hispaniola, the island now shared by Haiti and the Dominican Republic, and Cuba. Upon his return, the Cuban Indians pointed him to the island of Jamaica.
When Columbus arrived on May 5, 1494 at a bay he named Santa Gloria, the Taínos greeted him with great hostility and forced him to stay at sea. Santa Gloria, now St. Ann's Bay, was so named because Columbus felt that Jamaica was the most beautiful island he'd seen. Blank shot drove away the Taíno's warrior-laden canoes at this harbor.
Unfortunately for both Columbus and the Taínos, Columbus had arrived at a densely populated area of the island. His arrival was no more welcome along the shore at Puerto Bueno (later Dry Harbour, now Discovery Bay), where Columbus did land. Here he forced his way onto land with crossbows and even a dog, which bit several of the Taínos. He needed wood and water, as well as time to repair the ships. When he landed, Columbus claimed the land in the name of Ferdinand and Isabella of Spain.
The day after Columbus landed, six Indians arrived at the ship offering cassava, fruit, and fish. In fact, they supplied the Spanish for the remainder of their stay, and often throughout history, in exchange for trinkets and other goods. However, Columbus was disappointed by the lack of the gold he was told existed on the island.
Columbus decided to move on and landed again at what is now Montego Bay. He called this El Golfo de Buen Tiempo, "Fair Weather Gulf." Here his crew brought an Indian aboard who asked to travel with them, despite the protests of his family. From here Columbus led the ships back to Cuba, and then to the western coast of Jamaica.
The Taínos living in the southern and western areas of the island were more friendly and welcoming to Columbus' men. Columbus also stopped in Portland Bight, which he named Bahía de la Vaca, or "Cow Bay," perhaps due to the number of "sea-cows" (manatees) that he saw in the waters there. Columbus said that he found the most intelligent and civilized natives of all those he met in the Caribbean in the many villages near this bay.
He's also said to have had an interesting conversation, with the help of an interpreter, with a local chief, or cacique. The cacique and his entourage, which included his family and top members of his village, came vibrantly decorated in feathers, paint, and ornaments. However, the cacique is said to have asked Columbus to take him and his family with Columbus on his return voyage to Spain. The cacique said that stories were told that there was no match for Columbus' power, and he wanted to see the wonders of Spain if he was to be deprived of his land and authority. However, Columbus did not take them with him, and stopped only at Morant Point before he left for Hispaniola.
Columbus returned to the Caribbean twice more in his lifetime, but only returned to Jamaica on his final voyage. This last trip turned out to be far more troublesome than his second, and his stay on Jamaica less pleasant.
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