Haiti has the largest Afro-Caribbean population (nearly 11 million) and also has the highest percentage of its population originating from the African diaspora (95%).

The archipelagos and islands of the Caribbean Sea were the first places of settlement of Africans in the western Atlantic in the post-Columbian era. In particular, Pedro Alonso Niño, a black Spanish navigator, piloted one of Columbus’ ships in 1492. He returned in 1499, but did not settle. In the early 16th century more and more Africans became part of the population of the Spanish Caribbean colonies, sometimes as freedmen, but more often as slaves and laborers. The demand for African labor increased in the Caribbean because of the mass deaths of the Taino and other indigenous peoples, mainly as a result of Eurasian infectious diseases to which they had no immunity, as well as conflict with the Spanish and harsh working conditions. By the mid-16th century, the slave trade from Africa to the Caribbean was so lucrative that Englishmen Francis Drake and John Hawkins engaged in piracy and broke Spanish colonial laws to forcibly transport some 1,500 enslaved people from Sierra Leone to Española (Haiti and the Dominican Republic ).

During the 17th and 18th centuries, European colonialism in the Caribbean relied increasingly on plantation slavery, so that by the end of the 18th century Afro-Caribbean enslaved people outnumbered their European masters on many islands. A total of 1,840,000 slaves arrived in other British colonies, mainly in the West Indies of the Caribbean.

Beginning in the late 18th century, harsh conditions, constant inter-imperial wars, and a growing number of people of rights goals led to the Haitian Revolution in the French colony of Saint-Domingue, led by Toussaint L’Ouverture and Jean Jacques Dessalines. In 1804 Haiti, with an overwhelming majority of black slaves and leadership, became the second nation in America to achieve independence from the European state and establish a republic. Continuous waves of rebellions, such as the Baptist War led by Sam Sharpe in Jamaica, set the stage for the gradual abolition of slavery in the region, with Great Britain abolishing it in 1838. Cuba (under the Spanish crown) was the last island to free its slaves.

During the 20th century, Afro-Caribbeans began to assert their cultural, economic, and political rights on the world stage. Jamaican Marcus Garvey formed the UNIA movement in the United States, continuing the Aimé Césaire Negritude movement, which sought to create a pan-Africanist movement along national lines. Beginning in the 1960s, the former slave population of the Caribbean began to gain independence from British colonial rule. They were pioneers in the creation of new cultural forms such as calypso, reggae music and Rastafarianism in the Caribbean.