1490s establishments in the Spanish West Indies

Haiti, officially the Republic of Haiti, is a country in the Caribbean on the island of Hispaniola in the Caribbean Sea, east of Cuba and Jamaica and south of the Bahamas. It occupies the western side of the island, which it shares with the Dominican Republic. Haiti is the third largest country in the Caribbean by area, and with an estimated population of 11.4 million, it is the most populous Caribbean country. The capital and largest city is Port-au-Prince.

Dominican Republic is a country on the Caribbean island of Hispaniola in the Greater Antilles of the Caribbean Sea in the North Atlantic Ocean. It shares a maritime border with Puerto Rico to the east and a land border with Haiti to the west, occupying the eastern five-eighths of Hispaniola which, along with Saint Martin, is one of only two islands in the Caribbean shared by two sovereign states. In the Antilles, the country is the second-largest nation by area after Cuba at 48,671 square kilometers (18,792 sq mi) and second-largest by population after Haiti with approximately 11.4 million people in 2024, of whom 3.6 million reside in the metropolitan area of Santo Domingo, the capital city.

Puerto Rico, officially the Commonwealth of Puerto Rico, is a self-governing Caribbean archipelago and island organized as an unincorporated territory of the United States under the designation of commonwealth. It is located between the Dominican Republic in the Greater Antilles and the U.S. Virgin Islands in the Lesser Antilles. Located about 1,000 miles (1,600 km) southeast of Miami, Florida, it consists of the eponymous main island and numerous smaller islands, including Vieques, Culebra, and Mona. With approximately 3.2 million people, it is divided into 78 municipalities, of which the most populous is the capital municipality of San Juan, followed by those within the San Juan metropolitan area. Spanish and English are the official languages of the government, though Spanish predominates.

city in the Dominican Republic

Spanish possession in the Caribbean between 1492-1898

Spanish 1493-1821 possession in the Caribbean