5 Cities That Bring Colonial Cuba to Life

06/11/2015 12:25 pm ET | Updated Jun 11, 2016

By: Fiona Moriarty, Hipmunk

We're used to seeing images that portray Cuba as a time capsule, where colorful, 1950s-era American cars still rule the streets. But our long-isolated Caribbean neighbor's knack for preserving the past doesn't stop there. So we've rounded up five cities whose historic districts date as far back as the arrival of Spanish settlements in the early 16th century. Intrepid travelers determined to visit the island before the floodgates open will want to add these places to their itineraries, because there's just something so swashbucklingly romantic about cannons in the tropics.

1. Have a look at history in Havana

Colonial flair abounds in Habana Vieja, the historic district of Havana. Soak in the ambiance at any of five stunning plazas that showcase majestic neoclassical and baroque architecture, and marvel at the 16th- and 17th-century castillos that protected the city from pirate incursions of yore.

2. Stroll through tranquil Trinidad

Plaza Mayor is the pastel heart of this tranquil town in central Cuba, which boasts "one of the best collections of colonial architecture in the Americas," in the words of Smithsonian magazine. A UNESCO world heritage site, Trinidad is practically a living museum, but it's also home to an actual Museum of Colonial Architecture complete with a recreated 19th-century bathroom.

3. Visit the home of a conquistador in Santiago de Cuba

While known for being the scene of pivotal events of the modern Cuban Revolution, Santiago de Cuba's history stretches back to the beginnings of the colonial era. Highlights include the spectacular Castillo de San Pedro de la Roca, a 17th-century cliffside fort that towers over the Bay of Santiago, and Casa de Diego Velázquez, the oldest residence in Cuba and once home to the eponymous conquistador and colonial governor.

4. Explore the history of the Taíno people in Baracoa

Baracoa was the first Spanish settlement in Cuba, and its seclusion between lush mountain rainforests and waters of the Atlantic Ocean has helped preserve the remote, exotic atmosphere of its earliest days as a colonial village. Visit the Museo Municipal in Fuerte Matachín to learn the story of the Taíno Indians, who settled here long before the Spanish did.

5. Enjoy the 19th-century elegance of Cienfuegos
Founded during the late colonial period in 1819, Cienfuegos' luminous neoclassical architecture and modern layout have earned it the nickname "Pearl of the South." The gilded façade of the Tomás Terry Theater testifies to the town's former prosperity as trading center for sugar, coffee and tobacco. Thanks to the influence of its first settlers, who were of French origin, visitors to Cienfuegos enjoy a certain je ne sais quoi in the air that has endured through the years.