The West Indies saw the first landfall of Columbus, and by 1507 the Caribbean had attracted colonists from Spain. By the reign of Elizabeth I, Spanish sea power had become a threat to England, and Elizabeth's 'sea dogs' took the fight across the Atlantic, where the islands of the West Indies became pawns in attacks on the Spanish Main (i.e., mainland). The area soon teemed with pirates and privateers. The first British settlers, emigres rather than colonists, appeared c. 1620 as an offshoot from the North American mainland.

The earliest permanent British settlement was established on St Christopher in 1624. Barbados was founded in 1627. The idea of planting sugar as a staple crop, copied from Dutch settlers on the Guiana coast, led to the importing first of poor indentured servants from the British Isles and, later, to the wholesale shipment of slaves taken in Africa to work the plantations.

Permanent colonization for political as well as economic ends started with Cromwell (Jamaica, 1655). Various commissions and councils for foreign plantations sat from 1625, and the Lords of Trade and Plantations became the Board of Trade in 1696. For two centuries the West Indies figured as a commercial prize in all the wars of rivalry between Britain, France, Holland and Spain, disputed islands changing hands constantly. The indigenous peoples virtually disappeared.

The abolition of the British slave trade in 1807 cut off the plantations' supply of labour and the emancipation of slaves in 1833 made necessary the recruitment of indentured labour from India. Free Trade policies and cheap railway transport on larger islands altered the balance in favour of Cuba until, in the late 19th century, the success of the European sugar beet industry ruined the West Indian monopoly. The sugar industry gave place to bananas, cocoa and cotton. More recently tourism has become increasingly important.

The British islands have gone through the political gamut of unsuccessful federation. Up to 1671 the smaller islands were administered as a group. In 1671 the Leeward Islands, consisting of Antigua, St Kitts, Montserrat, the Virgin Islands and Nevis, were separated from Barbados and the Windward Islands (most of which were to be disputed with other powers until 1763) and given a governor-in-chief. A federal legislature existed until 1816, when the group broke in two; Antigua and Montserrat formed one division and St Kitts, Nevis and the Virgin Islands the other. In 1833 they were reunited and Dominica was added. In 1871 the Leewards became a federal colony, though each separate island retained its own institutions.

In 1763 Grenada, St Vincent, Dominica and Tobago were united under the Government of the Southern Caribee Islands. Dominica was detached in 1771, St Vincent in 1776, and Tobago perforce on its cession in 1783 to France. In 1833 Grenada, St Vincent, Tobago (now restored to Britain) and Barbados were grouped to form the Windward Islands under a governor-in-chief. St Lucia was added in 1838. Barbados was separated in 1885; Tobago was detached to Trinidad in 1889, and Dominica was attached from the Leeward Islands on 31 December 1939.

A Federation of the West Indies, comprising Leewards, Windwards, Jamaica and Trinidad, was established on 3 January 1958. Jamaica seceded by referendum in 1961, Trinidad followed, and the federation was dissolved in February 1962. In 1967 various islands became 'associated states' of Britain, a new status of self-government, rather less than full independence within the Commonwealth.

Postal History
The earliest communications were with the respective mother country: Britain, France, Spain, and to a lesser extent Holland and Denmark. The British government relied even for official despatches on casual ships until, in 1702, Edmund Dummer, an ex-surveyor-general to the Navy, instituted a private packet service under government contract. The packets operated monthly from Falmouth (after 1705 Plymouth), serving Barbados, Antigua, Montserrat, Nevis, St Kitts and Jamaica. The round voyage took three to four months. The service ended in 1711.

The posts in the Spanish Indies were farmed to the Galindez de Carvajal family in 1514. Havana was one of the approved ports-of-call for Spanish merchantmen. Mail went mainly by casual ship until in 1764 Charles III decreed the Correos Maritimos (Maritime mail). A monthly packet was started in 1767 between Corunna and Havana, though the service was interrupted in time of war.

A British government packet service began in 1755, and postmasters in the main colonies were issued with hand-stamps. A monthly service was maintained despite hazards of war, piracy and mutiny. After 1783 packets left Falmouth on the first and third Wednesday of every month, and a system of inter-island schooners acted as mail distributors and collectors. Routes varied with changing conditions and fortunes of war. In 1820 all the postal services of the West Indies were overhauled.

British packet agents were required to collect prepaid postage on all letters despatched by British packet to foreign destinations, and were issued with 'Crowned circle' handstamps and datestamps. British packets also continued to serve islands which had become definitively French by the Congress of Vienna (1815), and British POs, PAs or packet agencies were set up wherever British consulates existed. Jacmel in Haiti, for example, had a British packet agency before 1830.

In 1840 the British packets were contracted out by the Admiralty to the Royal Mail Steam Packet Co. In 1842 the main RMS depot and coaling station was moved from Barbados to St Thomas in the Danish West Indies.

Prepayment of packet correspondence to British destinations was made compulsory in 1858. Accordingly various postmasters in the British West Indies urged the use of adhesives.

The postmaster-general authorized the use of British stamps for this purpose from 8 May 1858 not only in British islands but also at certain agencies on foreign soil. Stamps so used can be identified by cancellations. The practice was stopped on 1 May 1860 when the crowned circle handstamps were again used until colonial stamps were adopted in each colony.

In 1865 the French also set up postal packet agencies in connection with packet-boats of Compagnie General Transatlantique plying between Saint-Nazaire and Mexico or Panama, which served Martinique and Guadeloupe. French stamps are known used either alone or in combination from Caribbean agencies between 1862 and 1881. The stamps can only rarely be identified off cover by named octagonal datestamps: more usually they were cancelled by an anchor in a lozenge of dots (proclaiming usage but not location) and the datestamps placed alongside on the envelope.

The greater part of the Caribbean area joined the UPU between 1877 and 1881.