The extensive established relationship between Canada and the many nation states of the Caribbean/West Indies have been continuing throughout the history of both regions. Primarily these policies were based on the policies of European countries in the Americas. Now, after many of these nations of the Caribbean/West Indies and the Provinces of Canada have successfully managed their own self-government the relations between the two regions has grown and strengthened over the last three centuries New France and the French colonies in the Caribbean enjoyed a flourishing trade in the first part of the eighteenth century, with the fort of Louisburg acting as an important trading centre linking New France, the Caribbean and France. When Britain gained control over the northern half of the continent, these relations were largely severed as trade between North America and the British Caribbean holdings went almost completely through U.S. ports, especially Boston.

With the American Revolution, the Americans were, in theory, to be shut out of the British colonies by the Navigation Acts and other British laws. Canadian merchants, particularly those based in Halifax, strove to become the new leading trading partners. The trade with the Caribbean did become an important one for Halifax, but the British laws could do little to prevent American traders from continuing to play a central role. The merchants of the West Indies preferred dealing with the United States, which produced a greater variety of goods at lower prices than the Canadians. The weak Spanish Empire could do even less than the British to keep out foreign traders, and Canadian trade with Cuba and other Spanish holdings also rose in prominence. This trade peaked in the years immediately before Canadian Confederation. Canada shipped flour, corn, timber, and fish to the Caribbean, while sugar and rum moved north. In the Maritimes a prosperous sugar refining and rum industry arose based on these imports.