Prehistoric Indians, probably from Central America, migrated to the West Indies as early as 5000 B.C. They were followed by Arawak and Carib Indians, who began migrating from South America about the time of Christ. They had spread throughout the islands by the time Europeans arrived at the end of the 15th century.

The first explorer to reach the West Indies was Christopher Columbus in 1492. His first landfall was probably at either San Salvador (also called Watling Island) or Samana Cay, both in the Bahamas. Santo Domingo, the first permanent European colony in the New World, was founded on Hispaniola in 1496.

Spain began extensive colonization of the West Indies in the 1500's. Sugarcane plantations were set up, and the Indian population was enslaved to provide labor. But the Indians soon died out, and the Spanish began to import slaves from Africa.

During the 1600's British, Dutch, and French colonies were established, and bitter rivalry developed between the four nations. Piracy became common as trade increased between the Old World and the West Indian colonies. Many pirates had island bases from which they preyed on treasure ships carrying gold and silver from the New World to Spain.

By the 19th century, Great Britain had become the dominant power in the West Indies. A slave revolt in Hispaniola, 1791–1804, led to the establishment of two independent nations on that island—Haiti (1804) and the Dominican Republic (1844). Cuba and Puerto Rico, the last Spanish colonies in America, were ceded to the United States in 1898 after the Spanish-American War. Cuba was granted independence in 1902. Several British colonies were given their independence in the 20th century.

The United States intervened in the affairs of West Indian nations several times to maintain peace in the Caribbean. American forces occupied Haiti, 1915–34, and the Dominican Republic, 1916–24. When civil war broke out in the Dominican Republic in 1965, U.S. Marines were sent to help restore order. In 1983, the United States sent troops to Grenada to restore order after a radical Marxist group killed that nation's prime minister. In 1994, American troops occupied Haiti to provide for the peaceful return of elected leaders who earlier had been deposed in a military coup.