Jamaica lies to the south of Cuba, while the Cayman Islands are located to the west.

Europeans used the term Antillia as one of the mysterious lands featured on medieval charts, sometimes as an archipelago, sometimes as continuous land of greater or lesser extent, its location fluctuating mid-ocean between the Canary Islands and Eurasia.

At the beginning of the 16th century, the Spanish began to colonize the island of Puerto Rico.

The Haitian Revolution was the first and only successful anti-slavery and anti-colonial insurrection by self-liberated slaves; it established the independent nation of Haiti, the first in the Greater Antilles, the Caribbean, and Latin America as a whole.

U.S. military rule over the island lasted until 1902, when Cuba was granted formal independence.

With an area of 207,411 square kilometres (80,082 sq mi), not counting the Virgin Islands, the Greater Antilles constitute nearly 90% of the land mass of the entire West Indies,[4] as well as over 90% of its population.

The remainder of the land belongs to the archipelago of the Lesser Antilles, which is a chain of islands to the east, running north–south and encompassing the eastern edge of the Caribbean Sea where it meets the Atlantic Ocean, as well as to the south, running east–west off the northern coast of South America.

Obduction has scraped accumulated rock onto the North American plate, islands and intrusions have been formed by volcanism, and the local crust has become deformed in other ways.

The capital of the Dominican Republic, Santo Domingo, with a population of over 2 million, is the largest city in the Greater Antilles.

Cuba, the independent nation with the highest HDI, nevertheless ranks below Puerto Rico and the Cayman Islands, both of which are categorized as "very high".