7 Most Populous Caribbean Cities

The Caribbean Sea is home to about 700 islands, and while many of them were historically European colonies, today just a few remain as colonies or U.S. territories. The rest have become their own island nations. The islands are famous for their beautiful tropical weather, turquoise waters, and hotspots of biodiversity. This tranquil reputation was built alongside major cities full of friendly people and fascinating culture. Below, find a list of the seven biggest urban centers on these gorgeous islands.

1. Santo Domingo, Dominican Republic

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The biggest city in the Caribbean is Santo Domingo, the capital of the Dominican Republic, with a population of 3,658,648. It is on the nation’s busiest port on the banks of the Ozama River with a climate that is less sticky and hot than other tropical locations. It is the oldest city in the Western Hemisphere, at least in terms of those established by Europeans during colonization; in 1990, the historic district of Santo Domingo was designated a UNESCO World Heritage site. The city also has two prominent colonial monuments: the Renaissance-style cathedral finished in 1542 and the Columbus Lighthouse, which is said to house the remains of Christopher Columbus.

2. Port-au-Prince, Haiti

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The second most populous city in the Caribbean islands is Port-au-Prince, Haiti, with a population of 2,618,894. Most people living here are of African descent, though communities of Hispanics, Asians, and Europeans also exist. Expect the standard wet and dry seasons of a tropical location, the wettest being the summer months. The region is known for its production and exportation of coffee and sugar.

3. San Juan, Puerto Rico

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San Juan, the capital of Puerto Rico, has 2,196,538 residents, and they are all U.S. citizens, as Puerto Rico is a U.S. territory. Most people are of Hispanic descent, and the region is known for rum and medicines. It is a popular tourist destination for those looking to experience a relaxed beach lifestyle as well as the history, culture, and excitement of Old Town San Juan. San Juan is also the busiest cruise port in the entire Caribbean.

4. Havana, Cuba

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Havana is Cuba’s capital city, and boasts a population of 2,117,625 people. Every year, they get about a million tourists to add to that. Havana is on the coast of Cuba, and visitors love its neoclassical, Art Deco, and colonial architecture alongside beautiful beaches. Because it was isolated from the United States for so long in terms of trade, the culture and lifestyle have also remained quite different from that of the rest of the Caribbean islands.

5. Kingston, Jamaica

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The population of Kingston is 1,190,763. Kingston is the capital of Jamaica, located in the southeast corner of the island right on the shore. Behind the city, you can see the island’s Blue Mountains. Aside from being a beach paradise because of its natural peninsula, the Palisadoes, the city itself contains modern buildings alongside crumbling architecture left over from the past, a striking sight to see.

6. Santiago de Cuba, Cuba

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The sixth-most populous Caribbean city is also in Cuba. Santiago de Cuba's population sits at 1,049,084, and it hosts a UNESCO World Heritage Biosphere Reserve, Baconao Park. It is a hot and humid city located in a bay and just below Cuba’s Maestra Mountains. Morro Castle, a fortress left over from colonial times, sits above the city on a bluff 200 feet high.

7. Santiago de los Caballeros, Dominican Republic

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More traditional than the Dominican Republic’s most populous city and capital is Santiago de los Caballeros (less formally known as just Santiago). It has a population of 891,674 and is on the north side of the island nation, residing on the Yaque del Norte River. The city was annihilated in 1662 by a massive earthquake but was rebuilt just a few miles away. You can still see the ruins of the old city in the San Francisco de Jacagua district.

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