| 1488 | | Rounding of the Cape of Good Hope |
| | | Bartholomew Dias, a Portuguese explorer was the first European to navigate around the southern tip of the African continent. |
| 1492 | Aug 3 | Columbus sets sail |
| | | With three ships, the Nina, the Pinta and the Santa Maria, Columbus set sail across the Atlantic in search of a route to the Far East. |
| Oct 12 | Christopher Columbus 'discovers' America |
| | | Christopher Columbus landed on what he thought was the east coast of Asia believing that there was no land between it and Europe but he had landed in the Caribbean and had discovered the 'Americas'. |
| 1493 | Nov 3 | Christopher Columbus discovers Dominica island |
| | | Christopher Columbus discovered Dominica island on a Sunday. The name is Latin for the word Sunday. The island should not be confused with the Dominican Republic which is a separate part of the Caribbean.
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| 1496 | Mar 5 | Henry VII and John Cabot |
| | | Henry VII granted John Cabot, his sons and heirs the power to explore unknown areas under the English flag. They were allowed to conquer these new lands. Although the Cabots had to fund the explorations themselves they only had to pay the Crown only one fifth of the money they made by selling the goods they found. |
| 1497 | May 2 | John Cabot sets sail for Asia |
| | | Under the English flag, John Cabot left Bristol on his voyage of exploration across the Atlantic to find a route to Asia and to open new trade routes. |
| Jun | Cabot discovers Newfoundland |
| | | Expecting to find the east coast of Asia Cabot and his fleet of explorers landed on what we now know as Newfoundland or Nova Scotia. |
| Aug 6 | Cabot returns from voyage |
| | | John Cabot returned to Bristol after his voyage of discovery. |
| Dec | Vasco de Gama rounds Cape of Good Hope |
| | | Vasco de Gama rounded the Cape of Good Hope to reach East Asia.
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| 1498 | May | Cabot disappears on voyage |
| | | Cabot and a fleet of five ships sailed for America but were not heard from again. |
| 1519 | Aug 10 | Magellan leaves Seville |
| | | Ferdinand Magellan set sail from Seville with five ships in search of a passageway to the south of South America in order to reach the Pacific Ocean and the Far East. |