- Ciboney, Arawak, Taino and Carib cultures (Pre-European era)
- Christopher Columbus reports seeing Antigua and Barbuda (1493)
- British settlement in St. Kitts (1623)
- French settlement in St. Kitts (1625)
- British settlement in Nevis (1628)
- Spain invades St. Kitts (1629)
- British Leeward Islands (1671-1816, 1833-1958)
- French siege of British St. Kitts (1689)
- Earthquake and tsunami (1690)
- Britain annexes French St. Kitts (1713)
- Battle of St. Kitts (1782)
- Slavery is abolished in St. Kitts (1834)
- Cholera epidemic (1853-1854)
- San Ciriaco hurricane (1899)
- West Indies Federation (1958-1962)
- Saint Kitts and Nevis gains independence (1983)
- Hurricane Georges (1998)
(This post includes any nation or civilization that occupied at least a portion of Saint Kitts and Nevis at some point. Unless specified otherwise, the dates correspond to when a nation or civilization existed, but do not necessarily correspond to occupation of Saint Kitts and Nevis.)