Anguila

Anguilla has probably been inhabited by the Caribbean since 1300 BC. The oldest remnants of a settlement dates from 600. According to some, the island was discovered by Christopher Columbus in 1493. It is certain that the Frenchman Pierre Laudonnaire visited the island in 1565.

The first colonial power that claimed the island was the Dutch West India Company in 1631. In that year they started building a small fort. The Spaniards conquered the island in 1633, and destroyed the fort. The stones were used by the Dutch to repair another fort on Sint Maarten. However, no traces of the former Dutch fort have been found, and its location is unknown.

In 1650 the island was colonized by British settlers, from Saint Kitts. They started growing maize and tobacco. In 1656, however, they were expelled by the Caribbean and in 1666 France occupied the island. A year later in 1667 the island became British again at the Peace of Breda. However, there remained disagreement between the British and French, as evidenced by the fact that from Anguilla the French part of Sint Maarten was occupied between 1744 and 1748.

When it is also on your bucket list:
picture source: http://www.elegantresorts.co.uk