The West Indies Federation, also known as the West Indies, the Federation of the West Indies or the West Indian Federation, was a short-lived political union that existed from 3 January 1958 to 31 May 1962. Various islands in the Caribbean that were part of the British Empire, including Trinidad and Tobago, Barbados, Jamaica, and those on the Leeward and Windward Islands, came together to form the Federation, with its capital in Port of Spain, Trinidad and Tobago. The expressed intention of the Federation was to create a political unit that would become independent from Britain as a single state — possibly similar to Canada, the Federation of Australia, or the Federation of Rhodesia and Nyasaland. Before that could happen, the Federation collapsed due to internal political conflicts over how it would be governed or function viably. The formation of a West Indian Federation was encouraged by the United Kingdom, but also requested by West Indian nationalists.

The Caribbean is a subregion of the Americas that includes the Caribbean Sea and its islands, some of which are surrounded by the Caribbean Sea and some of which border both the Caribbean Sea and the North Atlantic Ocean; the nearby coastal areas on the mainland are sometimes also included in the region. The region is south-east of the Gulf of Mexico and Northern America, east of Central America, and north of South America.