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| c. 1000 |
| | | Man-eating Caribs move into the islands around the sea named after them - the Caribbean | |
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| 1492 |
| | | The world's first globe is published by Martin Behaim without showing America, in the very year of Columbus' voyage | |
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| 1492 |
| | | After sailing for five weeks from the Canaries, Columbus and the Pinzón brothers step ashore in the Bahamas | |
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| 1492 |
| | | Columbus and his fellow explorers make landfall on the largest of the Caribbean islands, Cuba | |
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| 1496 |
| | | Diego Columbus, brother of the explorer, establishes the first secure Spanish colony at Santo Domingo | |
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| 1515 |
| | | The Spanish complete the conquest of Cuba and establish the town of Havana | |
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| 1609 |
| | | Castaways from an English vessel reach Bermuda, which becomes the first British island in the new world | |
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| 1627 |
| | | A British colony is founded in Barbados and within fifteen years has 18,000 settlers | |
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| 1655 |
| | | The British, settling in Jamaica, soon turn the island into the major slave market of the West Indies | |
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| 1697 |
| | | In the Treaty of Rijswijk, Spain cedes the western half of Hispaniola to France, which names its new colony Saint-Domingue | |
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