Trinidad and the nearby Valle de los Ingenios

Located in central Cuba, the town of Trinidad and the nearby Valle de los Ingenios (“Sugar Mill Valley”) gained recognition and flourished from the late 18th century through the late 19th century thanks to the prosperity of the sugar industry. The former bell tower (pictured), which was converted into the Museo Nacional de la Lucha Contra Bandidos in 1986, is arguably the most recognizable building in all of Trinidad. The Valle de los Ingenios is now a “living museum,” featuring 75 former sugar mills and plantations.

Habana Vieja (Old Havana)

Full of narrow streets lined with beautiful baroque architecture and neoclassical monuments, Old Havana — or, at the time, Havana — was founded in 1519 along Cuba’s northwestern shore. Encircled by former city walls and dotted with large plazas and fortresses, Old Havana, aka Habana Vieja, made the UNESCO World Heritage List in the early 1980s because of the vast number of ancient structures preserved over the course of several centuries.

San Pedro de la Roca Castle

Sitting atop a 200-foot-high peninsula at the entrance of the Santiago de Cuba Bay, San Pedro de la Roca Castle was built in 1638 to protect the port of Santiago from piracy because of conflicts between Spain and England. Converted to a prison in the 1800s, the former fortress now acts as a pirate museum and is considered one of many fortresses that helped define Cuba during the 17th century.

First Coffee Plantations in the Southeast of Cuba

After the Haitian slave revolt in the late 1700s, French immigrants began defecting to Cuba, and Santiago de Cuba in particular. Once there, they set up coffee plantations and built beautiful stone mansions on the land. La Isabelica (pictured), which was named after the owner’s slave mistress-turned-wife, now acts as a museum, housing several pieces of original furniture and various instruments used to cultivate the crop during the 1800s.

The Urban Historic Center of Cienfuegos

Most of the neoclassical buildings in the historic city center of Cienfuegos remain unharmed by human touch, but because of the city’s location on the bay, several of the structures have been damaged by hurricanes. While renovations occur after a natural disaster, the city center is still considered to be the best example of 19th-century urban-planning principles used by the Spanish. The streets are designed to be straight and symmetric, with monumental buildings lining them on each side, including the iconic former City Hall (pictured).

Valle de Vinales

Located in the Pinar del Rio province in the Sierra de los Organos (“Organs Mountain Range”), Valle de Vinales has become a popular tourist destination, thanks to its stunning scenery, vast limestone rock faces for climbing and many hiking trails. Considered to be one of the lushest parts of the island, Valle de Vinales houses some of Cuba’s — and the world’s — best tobacco plantations.

Parque Nacional Alejandro de Humboldt

Regarded by UNESCO as “one of the most biologically diverse tropical island sites on Earth,” Alejandro de Humboldt National Park is home to several plants and species endemic to the Guantanamo region of Cuba. Because it has such a large number of native inhabitants and a wide range of ecosystems, the park has gained global recognition and is one of the most well-preserved parks in the world.

The Historic Center of Camaguey

From art deco and art nouveau to neoclassical and neocolonial, the historic center of Camaguey is filled with architecture influenced by several different styles from past centuries. The third-largest city in the country is known for its numerous churches, which fill Camaguey with history and Cuban heritage.