This article is about the Caribbean island group. For the western Society Islands in French Polynesia, see Leeward Islands (Society Islands); The Northwestern Hawaiian Islands are also sometimes called the Leeward Islands.

The Leeward Islands are the northern islands of the Lesser Antilles. They are called "leeward" because the prevailing winds in the area blow from south to north. Thus, the Leeward Islands are downwind, on the backside, or leeward from the Windward Islands, the group of islands that first meet the Trade Winds coming from the south.

The Leeward Islands also refers to a British colony in these islands, consisting of Antigua, Barbuda, the British Virgin Islands, Montserrat, Saint Kitts, Nevis, Anguilla and (to 1940) Dominica, from 1671 to 1816 and again from 1833 to 1960. The colony was known as the Federal Colony of the Leeward Islands from 1871 to 1956 and the Territory of the Leeward Islands from 1956 to 1960.

The Leeward Islands:

• The Virgin Islands
• Anguilla
• Saint Martin (Guadeloupe (north part) and Netherlands Antilles (south part))
• Saba (Netherlands Antilles)
• Sint Eustatius (Netherlands Antilles)
• Saint Barthélemy
• Antigua
• Barbuda
• Saint Kitts
• Nevis
• Montserrat
• Guadeloupe
• Dominica

The tiny and remote Isla Aves may perhaps be included with this group for convenience.

However, the Netherlands Antilles are divided into the groups in the northeast and the southwest, with different naming conventions, see Netherlands Antilles.

Postage stamps

The British Leeward Islands - Antigua, Dominica, Montserrat, Nevis, St. Christopher (St. Kitts), and the Virgin Islands all used postage stamps inscribed "LEEWARD ISLANDS" between 1890 and 1 July 1956, often concurrently with stamps inscribed with the colony's name.

The issue of 1890 was a key plate design with the usual profile of Queen Victoria, eight values ranging from 1/2d to 5 shillings. In 1897 they were overprinted with a logo commemorating Victoria's Diamond Jubilee, and in 1902 the 4, 6, and 7d were surcharged with a value of 1d.

The 1890 issue design was also used for stamps of King Edward VII, as well as for King George V and George VI, with several changes of watermark and colors. In 1928 a large one-pound stamp was introduced, and updated for the new monarch when George VI took the throne.

The common design commemorative stamps of the Commonwealth between 1946 and 1949 included stamps inscribed "LEEWARD ISLANDS". In 1951 the West Indies University issue reflected the changeover to cents and dollars, as did the Queen Elizabeth II definitive series of 1954.