This Is the Best ‘Cultural Destination’ in the Caribbean

The World Travel Awards named Cuba the Caribbean’s Best Cultural Destination year this year — beating out other historical gems like Bermuda, Puerto Rico, and Martinique. Immediately upon arriving in Havana, the capital, it’s easy to see why the island has earned this distinction for the fourth consecutive year.

Old Havana (“Old Havana”), a UNESCO World Heritage Site is full of architectural gems that tell the city’s story, from Spanish rule to independence and political revolution. Royal Force Castlebuilt in the 1500s to defend against attacks during the colonial period, is one of the oldest forts in the Americas. The Capitol, an imposing neoclassical structure built in 1929 to house the Cuban Congress, offers a peek into the country’s early independence era. At the Plaza de la Revolución, giant murals of Che Guevara and Camila Cienfuegos adorn nearby buildings, standing as lasting reminders of the Cuban Revolution.

While exploring these sights on foot is possible, a better way to get around is in one of the many vintage cars from the 1940s and ’50s, where you will see zipping around Havana’s streets. These colorful cars, known as almendron, have been repeatedly and beautifully restored since the 1962 American embargo made importing new models nearly impossible. Not just for tourists, these vehicles also serve as public transportation for locals and represent an important part of Cuban history and ingenuity.

Make sure to park your vintage Ford Falcon long enough to visit a couple of Havana’s iconic museums. At the Museum of the Revolution, the former presidential palace, you will experience Cuba’s journey to revolution through a series of gory artifacts — like blood-soaked uniforms and bullet holes from an unsuccessful presidential assassination attempt. The National Museum of Fine Artsmeanwhile, tells the country’s history through art. A standout is Víctor Manuel’s Gitana Tropical from 1929, an avant-garde portrait of a mestiza woman often credited with the start of Cuba’s modern art movement.

No cultural exploration of Cuba would be complete without experiencing the island’s vibrant food and music scene. Palate La Guarida — a rooftop restaurant located atop a crumbling yet majestic mansion built in 1913 — offers modern takes on Cuban cuisine and wraparound views of Havana. The restaurant is also prominently featured in the 1994 film Strawberry and Chocolate, acclaimed for its role in shifting public attitudes towards the country’s LGBTQ community. For a classic mojito and live performances of Cuban son, salsa, and bolero music, head to Cafe Tavern. For more modern music, do your best to keep up on the dance floors of Cuban Art Factorya sprawling cultural space with art galleries, live music, DJs, and dancing.

As a reminder, U.S. citizens can’t legally travel to Cuba as tourists but can enter the country in several other ways, such as for educational purposes or cultural explorations. While it is possible to arrange such a trip on your own, Cuba can be a complicated place to navigate for outsiders. For the most culturally rich and hassle-free experience, consider booking a tour with companies like Summer Forever Travel or Exeter Latin America.