The term British West Indies refers to the former English and British colonies and the present-day Overseas Territories of the United Kingdom in the Caribbean.
In the history of the British West Indies there have been several attempts at political unions. These attempts have occurred over a period of more than 300 years, from 1627 to 1958, and were carried out, or sometimes imposed, first by the English and then the British government. During this time, some of the attempted unions were true federations of colonies and others involved attaching various colonies to a major, nearby colony for the purposes of cheaper, efficient government or because the attached colonies were too small to justify a governor and administration of their own.
The initial federal attempts never went so far as to try to encompass all of the British West Indies (BWI), but were more regional in scope. The historical regional groupings were the British Leeward Islands, the British Windward Islands, and Jamaica with other nearby English/British colonies such as the Cayman Islands, British Honduras and the Turks and Caicos Islands.
Many of the national government efforts to unify the region were met with opposition from influential groups within the various colonies (usually the planters), and in particular by opposition from the wealthier colonies. The colonies competed with each other in the markets of selling sugar and other commodity crops (such as bananas) to Great Britain; their rivalry contributed to opposition to a regional colonial federation. In addition, the poor development of communication links and travel links among the separated island colonies contributed to the insularity and development of separate identities of each colony, even after emancipation of the slaves and more widespread participation in political life.
All of these factors were partly responsible for the failure of some of the attempts at union. Some factors re-appeared during the short life of the Federation of the West Indies in the late twentieth century. The West Indies Federation of 1958 was the most ambitious effort to create a unified federation. The history of the previous attempts at federations and unions contributed to the failure of the 1958 Federation.