Starting with the Virgin Islands east of Puerto Rico, they extend southeast to Guadeloupe and its dependencies.

The more southerly part of this chain, starting with Dominica, is called the Windward Islands.

In sailing terminology, "windward" means towards the source of the wind (upwind), while "leeward" is the opposite direction (downwind).

Therefore, a sailing vessel departing from the British Gold Coast and the Gulf of Guinea, driven by the trade winds, would usually first encounter Dominica and Martinique,[1] islands most to windward, in their west-northwesterly heading to the final destinations in the Caribbean, Central America, and Northern America.

The early Spanish explorers called Puerto Rico and the islands to the west Sotavento, meaning "leeward".

[4] However, even in modern usage in languages other than English, notably Dutch, French, and Spanish, all of the Lesser Antilles from the Virgin Islands to Trinidad and Tobago are known as the Windward Islands (Bovenwindse Eilanden in Dutch, Îles du Vent in French, and Islas de Barlovento in Spanish).

Over the century leading up to Columbus' arrival in the Caribbean archipelago in 1492, the Caribs mostly displaced the Maipurean-speaking Taínos, who settled the island chains earlier in history, by warfare, extermination, and assimilation.

Although comparatively much smaller than the surrounding islands in the Caribbean, the Leeward Islands posed the most significant rebellion to the British Stamp Act, though it was decidedly less severe in comparison to that of the mainland North American colonies.