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| 1577 |
| | Francis Drake sails from Plymouth, heading west for the Pacific and the East Indies | |
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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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| 1761 |
| | John Harrison's fourth chronometer is only five seconds out at the end of a test journey from England to Jamaica | |
| | Harrison's 1st Marine Timekeeper National Maritime Museum
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| 1793 |
| | Britain joins other European nations in war against France, mainly in naval engagements in the West Indies and Atlantic | |
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| 1793 |
| | Toussaint L'Ouverture, a former slave, joins a Spanish force invading the French colony of Saint-Domingue (now Haiti) | |
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| 1800 |
| | Toussaint L'Ouverture emerges as the leader of Saint-Domingue, ruling without French colonial control | |
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| 1801 |
| | Toussaint L'Ouverture invades the neighbouring Spanish colony of Santo Domingo, and becomes ruler of of the whole island of Hispaniola | |
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