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| 1492 |
| | | Christopher Columbus, together with the brothers Martin and Vicente Pinzón, sails west from Palos in Spain | |
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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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| 1493 |
| | | Columbus returns to Spain, landing at Palos with news of his great discoveries | |
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| 1493 |
| | | Pope Alexander VI draws a line through the Atlantic, dividing new discoveries between Spain (west) and Portugal (east) | |
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| 1496 |
| | | Diego Columbus, brother of the explorer, establishes the first secure Spanish colony at Santo Domingo | |
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| 1497 |
| | | Henry VII commissions the Italian navigator John Cabot to cross the Atlantic in search of new territories for England | |
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| 1497 |
| | | John Cabot, searching for a trade route to China, probably reaches Newfoundland | |
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| c. 1500 |
| | | European diseases bring death on a massive scale to an American population that has no immunity | |
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| 1513 |
| | | Vasco Núñez de Balboa reaches the Pacific coast and claims the ocean for the king of Spain | |
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