We head toward the old sugar towns of Cienfuegos and Trinidad, on the south coast. The autopista is in varying degrees of decay and use, and Oscar dodges giant potholes, horse-drawn carts, huge tourist buses, and wheezing old Ladas, sometimes all at once. Never mind: The two towns are a revelation.

Cienfuegos is a symphony of classical Spanish architecture, with an 1870 cathedral and the 1889 Teatro Tomás Terry, which is, rather amazingly, still named after a local slave-owning sugar baron. The Cuban Croesus, as he has been called, made his fortune, in part, by acquiring ailing slaves, treating them, and reselling them. As with so many of Cuba's grand buildings, the interior is slightly worn, but it is a beautiful creation constructed almost entirely of Cuban hardwoods. We walk in on a rehearsal of a local production that could have been taking place a century ago.

Trinidad, where we spend the night, is another stunning, slightly disheveled place of pleasure. Once the island's sugar capital—it is called the Valle de los Ingenios ("Valley of the Sugar Mills")—it's now all sleepy pastel-colored buildings and cobblestoned streets. But it explodes into life at night, when the Casa de la Música lights up—a swirl of music and dance in the small outdoor amphitheater. Tonight there is an audience of some 250, including 50 or 60 tourists, nearly everyone dancing as the twelve-piece band plays salsa, reggae, and Cuban hip-hop. All the joie de vivre of Cuba seems to be concentrated in this one moonlit spot—the heady exuberance of the music, the heat, the sensuality of the dancers, the uncomplicated friendliness of the people. Unlike Havana, which like all capitals has an undercurrent of hustle and sleaze, Trinidad seems the epitome of innocent pleasure—provincial people having a good time, and welcoming visitors.

This is what Cuba did to me on several occasions: It disarmed me. When three men sat right beside us at the Trinidad Casa, my first thought was that they might mug us. When they smiled, we smiled back nervously and mentally secured our wallets. But then all three stood, walked to the stage and took up their instruments—trombone, guitar, and drumsticks. They were being friendly, and we were paranoid tourists. (My naturally suspicious nature is vindicated later, when I fall victim to a credit card scam—but more on that later.)

In the morning, we head back to Havana, wending our way north into the verdant hills called the Alturas de Santa Clara, through small villages, past ox wagons pulling agricultural goods from one small settlement to another, past real cowboys on horseback.

Oscar, our guide, opens up a bit and talks about life in Cuba. He describes himself as a humanist and says that he is not a member of the Communist party. His sister, an economist, earns about fourteen dollars a month, plus an annual bonus of thirty-three dollars. Oscar admits that it's a struggle, although I do not once hear him criticize the government directly in the eight days we are together.