Americans Can Fly Nonstop To These 4 Gorgeous Colonial Cities In The Caribbean

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We all love the Caribbean for its paradisaical white-sand beaches, seas of the most impossible turquoise color, and of course, the luxurious all-inclusives where even commoners like us get treated like royalty.

That said, sometimes you want a little more than bottomless brunch and margaritas by the pool. Every now and then, the culture buff in you comes out, and glitzy Hotel Zones just don’t cut it.

But hey, we’re not exactly itching to fly across the pond to freeze our bottoms in Europe this season, either. Turns out, you don’t need to go to the Old Continent to get a taste of that historical flair.

These 5 stunning colonial cities in the Caribbean feel like an extension of Europe in the New World, minus the gray skies and rainy Fridays:

Cartagena, Colombia

Colombia’s colonial centerpiece, Cartagena is a culture-loaded city that’s been almost entirely preserved from colonial times.

Yes, it has skyscrapers and a chaotic commercial zone that doesn’t exactly set it apart from the rest of South America, but at its core, it houses a UNESCO-protected walled center, complete with cobble-paved lanes, horse-drawn carriages, and ornate Baroque churches.

On the edge of the Historic Center, Castillo de San Felipe de Barajas is a Spanish-built fortress on the shores of the Caribbean, with tunnels and hidden passageways galore for the history lovers.

If beaches are your main draw, you’re spoiled for choice: from the white sands of Playa Blanca to the palm-lined shores of the Islas del Rosario, postcard-perfect turquoise waters are always within easy reach.

Fly Nonstop From The U.S. To Cartagena, Colombia (CTG)

Willemstad, Curaçao

The capital of Curaçao, an island in the Dutch Caribbean that’s rapidly rising in popularity, Willemstad is a colonial gem yet to be (truly) discovered by the masses.

With Northern Mannerist houses à la Amsterdam, except they’re candy-colored, and vibrant street markets, where they sell not stroopwafels and salted hering, but fresh fruit and spicy curry takeouts, Willemstad is the perfect marriage between Dutch and creole cultures.

Nothing short of Amsterdam’s Caribbean spiritual sister, it is even traversed by canals, with a floating Queen Emma Bridge connecting the vibrant Punda and Otrobanda districts, where you’ll find traditional restaurants dishing out cornmeal dumpling soup, beef stew, and other Curaçao delicacies.

This is still the Caribbean, after all, and a short walk from the Historic Center, Mambo Beach has the white sands and calm waters you’re seeking, whereas Sea Aquarium Beach is dotted with lively bars and eateries, making it ideal for an easy, lively beach day.

Fly Nonstop From The U.S. To Willemstad, Curaçao (CTG)

Santo Domingo, Dominican Republic

The first city ever built by European settlers in the New World, Santo Domingo is an open-air museum typically overlooked by Punta Cana-bound travelers.

With a heavily-fortified bay, a landmark stone-built cathedral that dominates a cafe-lined central plaza, and a colorful colonial core peppered with family-owned cantinas, it is all the cultural Caribbean getaway you need to cleanse your palette.

Not to miss while exploring Santo Domingo’s UNESCO World Heritage Site of a Historic Center: the Catedral Primada, the oldest cathedral in the Americas, Alcázar de Colón, Columbus’ former palace, and Fortaleza Ozama, a 16th century fortress on the banks of Ozama River.

Santo Domingo may not be as resort-oriented as Punta Cana, but the neighboring Boca Chica also has bright-blue seas and white sands, and even better, it’s only a 30 min drive from the city.

Fly Nonstop From The U.S. To Santo Domingo, Dominican Republic (SDQ)

Santiago, Cuba

Forget Havana: Cuba’s hottest destination for 2025 is the offbeat, yet-to-be-ruined-by-the-masses Santiago.

It’s not the oldest European-settled city in the Americas, as Santiago takes precedence, but it’s among the first to have been founded, with its starting date being traced back to 1515. Oh, and trust us when we say, it has the architectural grandeur to back it up:

A UNESCO World Heritage fort, Castillo del Morro has guarded Santiago Bay for centuries, and it is one of the best-preserved Spanish military sites in Cuba.

Over at Céspedes, the historic heart of the city, there’s a cathedral-backed main square, a landmark City Hall, and a plethora of museums and cafes to discover. It’s the perfect spot for soaking up the culture and experiencing Cuban life without the Havana crowds.

Other noteworthy attractions include Casa de Diego Velazquez, the oldest surviving house in Cuba, and the Santa Ifigenia Cemetery, where Cuban revolutionary heroes like José Martí and Fidel Castro rest.

Fly Nonstop From The U.S. To Santiago, Cuba (SCU)