8 Most Charming Historic Cities in the Caribbean

Visit these historic cities in the Caribbean for a rewarding, educative experience you’ll never forget!

Nothing is more romantic than a stroll down cobblestone streets, as you watch the blazing sun set over the harbor. And there’s no better place to do that than in the Caribbean.

Thanks to the era of colonization, European countries have left an indelible mark on the beachy landscape of the Caribbean islands. Walking down the road in Willemstad is akin to strolling the streets of a town in the Netherlands. Unmistakably Spanish architecture can be seen in the grand fort of San Felipe del Morro in San Juan.

Indeed, the Caribbean plays host to an incredible variety of historic landmarks– from ancient Mayan pyramids in Mexico to Hindu temples in Suriname.

There are so many historical cities to choose from in this region, it could take years to see them all. In addition, there are there are 23 UNESCO World Heritage sites, dispersed among 14 Caribbean islands.

So take your pick! Add some of these incredible historic cities in the Caribbean to your bucket list, and immerse yourself in the region’s amazing history.

1. Old Havana, Cuba

Old Havana showcases Spanish architecture and monuments in a tropical setting. (Via Casa Flamboyan)

Founded by the Spanish in 1519, architecture in this historic city reflects baroque and neoclassical styles. It was an important port and shipbuilding center during the 17th century. When French pirate Jacques de Sores plundered and burned Havana in 1555, the Spanish decided to add more fortresses and walls to protect the city.

Today, Havana is a UNESCO World Heritage Site and a popular destination for international travel. Famous must-visit sites are the Great Theatre of Havana, the Capitol building, the Museum of Fine Arts, Cathedral of Havana, and Castillo de la Real Fuerza.

2. Old San Juan, Puerto Rico

Castillo de San Felipe del Morro is sometimes called “El Morro” by locals . (Source: puertorico.com)

Blue cobblestone streets from colonial times are the star of the show in Puerto Rico’s charming capital city, San Juan. Stroll the historic district and visit various Spanish forts built to protect the town from invaders. You’ll find several of these at the top of a rocky cliff, overlooking the Caribbean Sea.

High stone walls still stand around the oldest part of the town, and the famous Castillo San Felipe del Morro, a large Spanish citadel, now features a museum that is open to the public.

3. Willemstad, Curacao

Traditional multi-colored townhouses line the waterfront in Willemstad, Curacao.

Also an UNESCO World Heritage Site since 1997, Willemstad blends European charm with Caribbean beauty. One of its main attractions is a unique wooden pontoon bridge that opens and closes to allow boats to pass through.

In addition, colorful 17th-century Dutch houses line the harbor, and there’s a floating market where local and foreign merchants sell fresh fish, spices, produce, and other goods.

There’s plenty to do in Willemstad, whether you’re interested in history museums or swimming with dolphins. In addition, luxury accommodations are numerous in the area, and so are eclectic shops where you can find an interesting assortment of souvenirs to take home.

4. Bridgetown, Barbados

At one time, Bridgetown, Barbados was a bustling British port. Mercantile boats often stopped there during their long trips across the Atlantic.

Today, the city’s 17th, 18th, and 19th century buildings are still well-preserved. Its importance as a major trade port led to its inclusion in the UNESCO World Heritage list of historic cities in the Caribbean in 2012.

While there, be sure to try typical Bajan cuisine, such as cou cou and flying fish, the national dish of Barbados.

5. Santo Domingo, Dominican Republic

The Alcazar de Colón is the oldest viceregal edifice in America, and the former home of Diego Columbus, the son of Christopher Columbus.

Santo Domingo was founded in 1498 by Bartholomew Columbus, the younger brother of Christopher Columbus. It is the oldest continually inhabited European settlement in the Americas.

While visiting the historic district of Santo Domingo, known as the Colonial Zone, be sure to pass through Plaza España. From this eclectic public square, you can see the Alcazar de Colón, The Royal Dockyards Museum (next to Trujillo fortress and Puerta de la Atarazana), the Palace of Communications, and the Reserve Bank.

6. Paramaribo, Suriname

The Saint Peter and Paul Cathedral, the largest wooden building in the Western Hemisphere.

You might hear of Paramaribo, Suriname described as a city for history lovers– that’s because it’s one of the most unique towns in the Caribbean, and has quite an interesting backstory. Blending Dutch, Indian, Spanish, South American, and indigenous cultures in its architectural styles.

Famous museums and landmarks include Saint Peter and Paul Cathedral, the largest wooden building in the Western Hemisphere, Fort Zeelandia, and the Presidential Palace of Suriname.

7. Oranjestad, Aruba

Built in 1798, Fort Zoutman is Aruba’s oldest building.

In Oranjestad, you’ll find a unique blend of new and old. Luxury stores and boutiques line the streets, scattered among historical buildings and quaint Dutch architecture.

Oranjestad is the capital of Aruba, a Dutch Caribbean island located near Bonaire and Curacao in the southern Caribbean Sea. Popular landmarks to visit are Fort Zoutman, Aruba’s oldest building, The Willem III Tower, and the Historical Museum.

8. Oranjestad, Sint Eustatius

Historic cities in the Caribbean. — Ruins by the sea in Oranjestad, Sint Eustatius.

Sint Eustatius may be well off the beaten path as far as Caribbean travel goes, but it’s just the ticket for those who want to visit historic cities in the Caribbean without the crowds.

This sleepy town was once a bustling hub on colonial trade routes. Today, it is home to the oldest synagogue in the Western Hemisphere, as well as many other 17th-century forts and buildings.

While most of these are well-preserved, one part of the old city is now submerged beneath the sea. Divers can explore these underwater ruins, and hiking enthusiasts can trek up The Quill, the island’s trademark stratovolcano.

Main image source: Getty Images

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