Traveling to Cuba is still a cold war pain in the ass – despite Fidel Castro's retirement. Yet nowhere in the world are Americans more welcome than in the arms of this island's sun-happy, rum-buzzed inhabitants. But getting your hands on a legal visa is tough at the last minute. Insight Cuba, a nonprofit travel outfit, specializes in this sort of thing. It has put together a five-day, "Jazz in Havana" tour that culminates in an raucous outdoor New Year's Eve party. One highlight: the government-run La Zorra y el Cuervo (The Fox and Crow) club. It's through an old English phone booth, down the stairs, and into an intimate 20-table room, where the country's best sax and trumpet players sweat it out with a traditional bata and maraca rhythm section.

These trips are about learning, so the next day will find you at the home of a local jazz cat who has played at Lincoln Center in New York. There, you'll learn about his life and his craft. But it gets really interesting when he starts playing. "The neighbors will come out, and things will erupt in a dance party right on the street," says Insight Cuba's CEO Tom Popper. On New Year's Eve, a local guide will take you to Cathedral Square, dominated by colonial-era buildings, for an all-night dinner party soaked in Creole mojitos, 12-year-old rum, and as much salsa dancing as you can handle. At midnight, stay back from the walls because that's when the locals indulge in their tradition of throwing old water out the window to wash away the old year.