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334km (208 miles) SE of Havana; 261km (162 miles) S of Varadero; 649km (403 miles) W of Santiago de Cuba

Tiny Trinidad is, quite simply, one of the finest colonial towns in all the Americas. Wholly disproportionate to its diminutive size, Trinidad ranks as one of Cuba's greatest attractions. A few square blocks of cobblestone streets, pretty pastel-colored 18th- and 19th-century houses, palaces, and plazas, Trinidad's colonial-era core can be toured in just a few hours. However, its serenity is so soothing that many visitors are easily coaxed into much longer stays. Magically frozen in time and tastefully scruffy where it needs to be, the city has streets that are more populated by horse-drawn carts than automobile traffic, and old folks still crouch by windows, behind fancy wrought-iron grilles, to peer out at passersby.

Founded in 1514 on the site of a native Taíno settlement, Villa de la Santísima Trinidad was the fourth of Diego Velázquez's original seven villas (towns). Trinidad quickly grew and later prospered in princely fashion from the sugar-cane industry concentrated in the outlying Valle de los Ingenios. The sugar boom that took root by the mid-1700s created a coterie of wealthy local sugar barons, who built magnificent estates in the valley and manor houses in town and imported thousands of African slaves to work the fields. Trinidad's golden age, though, proved to be short-lived. Slave uprisings on plantations, intense European competition, and, finally, independence struggles throughout the Caribbean all took their toll on the Cuban sugar industry.

When the bottom dropped out of sugar by the 1860s, Trinidad's economy collapsed and the town drifted into obscurity. Its economic failure in the late-19th century is a true blessing in the 21st: Trinidad escaped further economic development and modernization that surely would have obscured the colonial nucleus that UNESCO honored as a World Heritage Site in 1988. Even in the 1950s, in prerevolutionary, capitalist Cuba, the beauty and historical value of Trinidad prompted the government to declare it off-limits to further development.