Pinar del Río
Named for the stands of pine trees that once shaded the banks of the Río Guamá, this has been Cuba's tobacco city since its first land grants were allocated in 1544. Viñales and Vuelta Abajo were the island's great tobacco plantations, and Pinar del Río prospered as the tobacco market town and manufacturing center, even after the rest of the island turned almost exclusively to the cultivation and export of sugarcane.
Today the city (population 125,000) is distinguished by little more than its cigar factory, a distillery that produces guayabita (a brandylike liqueur made from sugarcane and guava), and its many fluted-columned and pillared porches in pastels that seem to reflect the red soil of the surrounding vegas. Pinar del Río doesn't have the atmosphere of Viñales, but a short layover here would provide a sampling of life in what is probably the most provincial of Cuba's provincial cities, an opportunity to drop in on Cuba au naturel.