6 Colorful Caribbean Towns You Need to Explore

Who doesn’t love a trip to the Caribbean? Those beautiful azure waters, sandy beaches, and near-constant perfect weather are all attractions that make the various islands a popular vacation destination. Even though the beaches get all the shine, there’s something to be said for setting aside at least one day during your Caribbean beach trip to explore a town or city. If your vacation is taking you to one of these popular islands, be sure to immerse yourself in their colorful towns.

Willemstad, Curaçao

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To call Willemstad, Curaçao, colorful is an understatement. The island’s capital city will have you wondering if you somehow teleported to Amsterdam instead of the Caribbean. This is because Curaçao is a Dutch Caribbean island where the locals will speak one of three languages: Dutch, English, or Papiamentu. Due to its history and vibrance, Willemstad is a UNESCO World Heritage Site. When you visit, you’ll enjoy the vibrant, painted buildings and the waterway that splits the town. Shop from the floating markets or book a stay in a 19th-century boutique hotel.

Old San Juan, Puerto Rico

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Puerto Rico is one of the few islands in the Caribbean that offers a unique draw specifically for travelers from the United States. If you’re a U.S. citizen, you don’t need a passport to visit. Home to some of the top-rated beaches in the world and the Bacardi factory, Puerto Rico is also rich with history. And if you’re a history buff who also loves architecture, then Old San Juan—a UNESCO World Heritage Site—should be on your list. The district is part of the original town that was built when the island was first colonized by the Spaniards. The colorful houses are built in a colonial style and butt up close behind the old Spanish fort, El Morro. Enjoy the cobblestone streets and drink in the vibrant shopping and nightlife throughout the district.

Old Havana, Cuba

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Now that Americans can legally travel to Cuba, there’s no reason not to visit the island nation that’s only 90 miles south of Miami, Florida. Most people know that Havana has a vintage quality to it, often because of the embargo placed by John F. Kennedy and upheld by countless presidents until recently. But even within Havana, there’s a colorful, older district that you’re going to want to visit. Old Havana, or “Havana Vieja," is really what people imagine when they think of the Cuban town. Vintage 1950s cars from the U.S. and the former Soviet Union, set against a backdrop of aging yet colorful architecture in the baroque and neoclassical styles, will have you snapping pictures all day long.

Cockburn Town, Grand Turk, Turks and Caicos

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Did you know that there are more than 40 islands within Turks and Caicos? Of those, only eight are inhabited, and the one you need to visit is Grand Turk Island. If you book a trip to this British Overseas Territory, be sure to stop into Cockburn Town. While only 3,700 people call Grand Turk home, the capital city is a popular stop for cruise ships. Not only is Cockburn Town the capital of Turks and Caicos, but it’s also a historic colonial site, complete with colorful homes and a beautiful museum. According to locals, this is where Christopher Columbus first arrived in the New World in 1492, not Hispaniola.

Santo Domingo, Dominican Republic

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A colorful tour of the Caribbean isn’t complete without a trip to Santo Domingo in the Dominican Republic. This nation that shares an island with Haiti is a popular tourist destination because of its sandy beaches, all-inclusive resorts, and friendly residents. But Santo Domingo holds a special place as the largest city in the Caribbean with over 3.6 million residents. In addition to colorful architecture and their own UNESCO World Heritage Site in the Colonial City district, this town is also a leader in “firsts” for the Western Hemisphere. Santo Domingo was the first to have a hospital, monastery, and a cathedral.

Roseau, Dominica

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If you’re not familiar with the Caribbean, it’s easy to assume someone made a mistake and meant to say the Dominican Republic instead of Dominica. But Dominica is a small island nation that passed through a number of hands during the European colonial period. First settled by Christopher Columbus in 1493, the indigenous people eventually pushed out the Spanish. However, they were also occupied by the French and British before gaining independence in 1967.

If you visit the capital city of Roseau, you’ll enjoy the colorful colonial buildings, old market, and the vintage spirit as you stroll through the streets. Another bonus is that Roseau is strategically located on the small island for easy day-trip access to popular nature excursions. Or stay in town and visit the Dominica Botanical Gardens, St. Patrick’s Catholic Cathedral, and the Dominica Museum.

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