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Spanish rule (1509–1655)

Christopher Columbus was the first European to see Jamaica, claiming the island for Spain after landing there in 1494 on his second voyage to the Americas. His probable landing point was Dry Harbour, called Discovery Bay, and St. Ann's Bay was named "Saint Gloria" by Columbus, as the first sighting of the land. He later returned in 1503; however, he was shipwrecked and he and his crew were forced to live on Jamaica for a year while waiting to be rescued.

One and a half kilometres west of St. Ann's Bay is the site of the first Spanish settlement on the island, Sevilla, which was established in 1509 by Juan de Esquivel but abandoned around 1524 because it was deemed unhealthy. The capital was moved to Spanish Town, then called St. Jago de la Vega, around 1534. Meanwhile, the Taínos began dying in large numbers, both from introduced diseases and from enslavement by the Spanish. As a result, the Spanish began importing slaves from Africa to the island.

Many slaves managed to escape, forming autonomous communities in remote and easily defended areas in the interior of Jamaica, mixing with the remaining Taino; these communities became known as Maroons. Many Jews fled the Spanish Inquisition to live on the island. They lived as conversos and were often persecuted by the Spanish rulers, and some turned to piracy against the Spanish Empire's shipping.

By the early 17th century it is estimated that no more than 2,500–3,000 people lived on Jamaica.