1510s establishments in the Spanish West Indies

Jamaica is an island country in the Caribbean, covering . It is the third-largest island in the Greater Antilles and the Caribbean, after Cuba and the island of Hispaniola. Jamaica lies about south of Cuba, west of Hispaniola (the island containing Haiti and the Dominican Republic), and southeast of the Cayman Islands (a British Overseas Territory). With million people, Jamaica is the third most populous Anglophone country in the Americas and the fourth most populous country in the Caribbean. Kingston is the country's capital and largest city.

Havana (, ; ) is the capital and largest city of Cuba. The heart of La Habana Province, Havana is the country's main port and commercial center. It is the most populous city, the largest by area, and the second-largest metropolitan area in the Caribbean region. The population in 2021 was inhabitants, and its area is for the capital city and 8,475.57 km2 for the metropolitan zone. Its official population was 1,749,964 inhabitants in 2024.

city and capital of the province of Santiago de Cuba, Cuba

Camagüey () is a city and municipality in central Cuba and is the nation's third-largest city with more than 333,000 inhabitants. It is the capital of the Camagüey Province.

town in the province of Sancti Spíritus, Cuba

city and municipality in Cuba

thumb|Urban agriculture in Bayamo

Baracoa, whose full original name is '''''' ('Our Lady of the Assumption of Baracoa'), is a municipality and city in Guantánamo Province near the eastern tip of Cuba. The area was visited by Admiral Christopher Columbus on November 27, 1492, and a settlement founded by the first governor of Cuba, the Spanish conquistador Diego Velázquez de Cuéllar on August 15, 1511. It is the oldest Spanish settlement in Cuba and was its first capital (the basis for its nickname '''''', 'First City').