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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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| 1496 |
| | Philip, heir to Austria, marries Joanna, a daughter of Ferdinand and Isabella of Spain, in the second of the great Habsburg marital alliances | |
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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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| 1515 |
| | The Spanish complete the conquest of Cuba and establish the town of Havana | |
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| 1516 |
| | The death of Ferdinand II results in Spain becoming part of the Habsburg empire, under the rule of Charles V (as Charles I of Spain) | |
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