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Trinidad has weathered five centuries with barely a wrinkle. Its enchanting cobblestone streets are lined with houses that have brightly painted adobe walls and wooden shutters. Its historic center, which covers more than 50 blocks, is like a vast, meticulously maintained museum full of restored mansions and manicured plazas. Yet it's also a lively town of 75,000, where the Trinitarios are not content merely to reside in a museum exhibit. They live here; they work here; they shop here. Come evening, they pull their chairs out onto the street to gossip, and the air rings with the songs of birds perched in wicker cages and of bands performing in bars or restaurants. Trinidad is one of Cuba's magical places, and it's much more manageable than Havana, to boot.

The city was founded in 1514 by the conquistador Diego Velázquez, who named the settlement for the Holy Trinity. It grew little until the 17th century, when its inhabitants began trading with pirates. Between 1750 and 1825, the population rose from 6,000 to 12,000, as thousands of slaves were brought in to work on sugar plantations in the nearby Valle de los Ingenios. Wealthy families built mansions, filled them with imported treasures, and sent their children to European schools. By the second half of the 19th century, however, Trinidad's star began to fade as sugar prices fell, the struggles for independence began, and slavery ended. By the early 1900s, Trinidad was impoverished and isolated. But the neglect that prevailed during the first half of the 20th century froze the city in a time warp that allowed it to retain its colonial ambience. In 1988, UNESCO declared the historic center a World Heritage Site, and during the past decade the government has worked hard to restore the colonial architecture.

Some people who visit Trinidad stay on the nearby Península de Ancón, but the advantages of staying in the city include many cultural sights and vibrant nightlife. Day-trip options—through such tour operators as Cubánacan—include treks to the beaches of Ancón, hikes in the Sierra de Escambray, train rides through sugar plantations, and sailing or diving excursions to Cayo Blanco. (Note that like many Cuban cities, Trinidad's streets go by pre- and postrevolutionary names. ) Since few Cuban cities wear their history on their sleeves the way Trinidad does, folks here are likely to use the traditional names.

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