To travel to Cuba—a journey that's becoming slowly, surely more possible thanks to the recent easing of travel restrictions—is, famously, to go back in time. Havana is imagined as a town caught in the 1950s. Trinidad, however, is to step even further back, into Spanish colonial days.

side street in Cuba
Credit: Jens Benninghofen / Alamy

The approach to Trinidad, midway down Cuba's southern coast, is flanked by the foothills of the Escambray mountain range and a glittering Caribbean sea. Except for a few hand-painted billboards bearing slogans like "Patria o Muerte" and "Viva La Revolución," there are few indications along this country road of human presence. Suddenly the street is paved with cobblestones and lined by humble single-story houses, their stucco exteriors painted in island pastels. These simple dwellings have been less meticulously restored than the sumptuous structures in the center, but throughout, there are few glimpses of the modern.

Trinidad was founded in 1514 by the Spanish conquistador Diego Velázquez de Cuéller; its fortunes rose with sugar. In the mid-19th century, Trinidad’s heyday, the town and its environs produced a full third of all of Cuba’s sugar exports; it was then that Trinidad acquired its elegant appearance. The political and economic upheavals of the last 150 years conspired to preserve it, and UNESCO designated the town and the surrounding valley a world heritage monument in 1988.

Today, Trinidad is one of Cuba’s major tourist destinations. But a major tourist destination in Cuba does not look like one elsewhere in the world; there are a few people with cameras wandering around, but mostly it feels like a serene country town that happens to be uncommonly lovely.

Here, a guide to the unique charms of Trinidad and its surrounding countryside.

The Grand Hotel Iberostar Trinidad: the place to stay
Trinidad’s sole luxury hotel boasts an elegant and airy atrium with marble floors and Spanish ochre walls; some rooms have large doors opening onto balconies that overlook the peaceful Parque Cespedes. More info, this way.

Sol y Son: atmospheric dining

One doesn’t go to Cuba for the food. For vegetarians, matters are all the more difficult; strangely, given Cuba’s tropical location, fruits and vegetables are scarce. Trinidad crawls with paladars, restaurants in private homes that sprouted up after self-employment was legally permitted in 1993. The considerable pleasure of passing the evening in the courtyard of this beautiful colonial home makes up for what it lacks in culinary distinction.

Simón Bolivar/Calle Desengaño 283; +53 41-992926

Palacio Cantero: a room with a view
Near the top of the town is the Plaza Mayor, shaded by majestic palm trees and surrounded by elaborate town houses that once belonged to the owners of nearby sugar plantations. Among the loveliest of these residences is the beautifully restored Palacio Cantero, the municipal history museum. A series of grand rooms with Italian marble checkerboard floors, high ceilings and muralled walls cluster around a central courtyard. The climb up its bell tower leads to a spectacular view of the Plaza Mayor. Off to the south, green flatlands lead to the sea; in all other directions, sun-baked hills rise to meet the sky.

Simón Bolivar/Calle Desengaño 423

Ingenio Manacas: Living history
A twenty-minute taxi ride from town leads to an unshaded circle of red earth in which women hawk colorfully embroidered white tablecloths. This is the central plaza of the Ingenio Manacas, a 19th-century sugar plantation and mill. The plantation owner’s family house, now a tourist restaurant, sits near a dense scattering of one-room shanties, some so primitive they might have been the original slave quarters. (The slave trade in Cuba flourished until the late 1860s; almost a million Africans were brought as slaves to Cuba in the course of its history, the large majority of these to work on sugar plantations.) In the midday heat, residents sit beneath scraggly trees next to pigs sprawled in the dirt. Once a place of brutal toil, the Ingenio Manacas now seems a place of brutal torpor.

Playa Ancón: A day at the beach
An excursion in the opposite direction from Trinidad to the nearby Playa Ancón makes for a delightfully indolent day. The beach is long, wide and remarkably deserted, the sea pristine and warm. Settle into a deck chair beneath one of the palm-frond umbrellas set out in front of the Soviet-era Hotel Ancón. With your back to this cruise-ship-sized monstrosity, you might forget it's there and even find yourself grateful for its presence come lunchtime, when it serves surprisingly good pizza and ice cream. More info, this way.

Biblioteca Municipal: Books and architecture
The Revolutionary government made education and literacy a priority. Its famous 1961 campaign to eradicate illiteracy — during which 100,000 people, mostly Cuban teenagers, were trained as teachers and sent into the countryside — is said to have been successful within the year. This national concern is evident in the appearance of Trinidad’s public library, a magnificent colonial hall with checkerboard floors and coffered ceilings painted in pink, blue, and gold. It has been as beautifully restored as some of the town’s major tourist attractions. More info, this way.

Casa de la Música: Dancing in the streets
After dark, Trinidad is quiet except for strains of traditional Cuban music issuing from just above the Plaza Mayor and beckoning Trinidad’s tourist population to the steps of the Casa de la Música. Cubans — lithe young women and elderly men, spectacular dancers and the merely superior — coax initially reluctant Europeans off the stairs and onto an empty portion of the plaza. By midnight, this little dance floor seethes. Buffered from deserted countryside by only a few silent blocks, this joyous party under the stars seems an isolated island, like Cuba itself.

Calle Cristo off Plaza Mayor, open nightly