The last five centuries have been an era of colonial occupation, followed by independence in the late 20th century for some islands. Large-scale sugar cane plantations on the more fertile islands led to the importation of thousands of slaves from Africa, and indentured labor from Europe and Asia after the abolition of slavery in the early part of the 19th century.

The islands were occupied by a variety of colonial powers. Anguilla was settled by Britain in 1650 and remains under British rule. There was a very brief era of French occupation in 1666, and a short period of self-proclaimed independence in the 1960s.

St Martin’s history is more turbulent. Christopher Columbus is believed to have landed there on St Martin’s day in 1493. He named it ‘Isla de St Martin’ and claimed it for Spain, but the Spanish never occupied it. The island was divided between the Netherlands and France in the 1648 Treaty of Concordia, but for the following 150 years ownership was disputed by the French, the Dutch and the British. The Treaty of Concordia resumed in 1816, and the island remains divided into the Dutch area of Saint Maarten and the French area of Saint Martin. In the 40-year period from 1960 to 2000 the island was devastated by three hurricanes, Donna, Luis and Lenny.

Antigua and Barbuda were established as British colonies from 1632 and shared in the sugar cane and slavery history common to most of the Leeward Islands. Construction of a British naval dockyard began in 1725, and the most famous officer to serve there was Captain (later Admiral) Horatio Nelson. The restored dockyard remains, as part of Antigua’s national park. The nation of Antigua and Barbuda gained independence from Britain in 1981.

St Kitts & Nevis were claimed for Spain by Christopher Columbus in 1493, but settled by the French from 1538. The British and French together wiped out the indigenous inhabitants and divided the island between them in the 1620s. Tobacco farming was introduced, followed by sugar cane and the inevitable African slaves. British and French rule alternated until 1783, when it became British. Independence from Britain was gained in 1983.

Montserrat is a British overseas territory first colonized in 1632. Its sugar cane, rum and slavery based economy largely failed in the 19th century, and agriculture mostly returned to subsistence smallholdings. In 1989 Hurricane Hugo damaged 90% of the island's buildings and crippled tourism. Further blows were dealt by the 1995 and 1997 eruptions of the Soufriere Hills volcano, which buried Plymouth, the capital, and killed nineteen people. Half the population left the island, and there was a further eruption in 2003. However, tourism is gradually recovering, following the construction of a new capital and airport.