A trip to Havana is the kind of vacation that can drive you to drink. After a few lazy days on the beach in Mexico's Playa Del Carmen, where the action slows down considerably after the last mahimahi dinner is served, I boarded a Cubana Airlines flight to Havana in search of some nightlife. As we climbed over the Gulf of Mexico, clouds of white smoke began billowing into the cabin of the Soviet-era clunker. In a panic I turned to the Cuban next to me. I thought we were done for. "Don't worry," he smirked. "It's just air-conditioning." I ordered a beer to settle my nerves, but I wasn't the only one on edge. The passengers applauded as we safely touched down.
As my taxi made its way to my hotel in Old Havana, we seemed to be moving backward in time, from the more contemporary, 1950s-style exterior of the city to its crumbling colonial core. Like the French Quarter in New Orleans, or the ancient neighborhoods of Rome, Old Havana entices you with its worn facades and narrow, lively streets. Amid the faded American cars that somehow keep running after a half century, enterprising Cubans hawked cheap cigars and chased tourists with offers to eat and sleep in their homes. Staying with locals is a great introduction to a different culture, but I had my sights set on the Sevilla Hotel, a monument to Cuba's decadent gangster past.
The restored colonial luxury hotel was a favorite for the likes of mafia boss Santo Trafficante Jr. and novelist Graham Greene, who supposedly wrote Our Man in Havana while staying in one of its cozy rooms. The main attraction must have been the Sevilla's seductively curved outdoor pool, with a well stocked bar nearby. I could easily have killed an entire weekend poolside drinking mojitos rather than, say, going out to eat. To put it mildly, Cuban restaurants are awful. Blame the embargo, blame Castro -- just don't order the fish. What pulled me away from the pool was a desire to hear some hot Cuban jazz.
I had seen one of Cuba's biggest names in jazz, Chucho Valdes, perform two electrifying sets on piano at New York City's Village Vanguard. His powerful, surging McCoy TynerÐesque sound hits you like a 12-piece orchestra. What's so unusual about ValdEs is how he seamlessly moves between traditional Cuban melodies and hard bebop riffs -- a merging of styles for which these musicians are justly famous. While in Cuba I had to hear more, but the problem was where. In Havana you won't stumble upon anything like Bourbon Street -- a strip of raucous music clubs filled with drunken revelers. The government's hysterically anti-imperialist newspaper didn't leave room for music listings, and my guidebook was similarly useless. I did see posters for blaring brass bands playing the big hotels, and combos doing Buena Vista Social Club crowd pleasers were hard to miss in the busy historic plazas. But to find a real music club, I had to ask around. It was one of the city's highly educated cabbies who led the way.
The driver said he had a master's in engineering yet made his living ferrying tourists around town. He brought me to a faceless building with all the charm of a DMV office. I paid a $10 cover in U.S. dollars, which are eagerly accepted virtually everywhere in Cuba. Inside, in a room stuffed with plastic chairs, folding tables, and sweaty bodies, I found at last what I had been looking for: On a small stage, a pack of drummers backed up a horn section playing Afro-Cuban tunes -- until a rapper stepped up. The result was an odd yet incredibly fresh Cuban hip-hop sound. Into the early morning I sipped tasty $2 rum drinks and cheered as the horn players and rappers traded improvisations, each coaxing the other to new heights. It was the kind of night that made getting onto a Cuban airplane worth the risk.
BREAKING THE BAN Officially the United States bans American tourists from spending money in Cuba, but countless U.S. citizens traveling through a third country like Mexico have not encountered problems. And Cuban officials don't stamp your passport, so as not to leave any evidence of your trip.
SMOKIN' TOUR The one site not to miss is Havana's Cigar Museum, featuring a dark, wood-paneled humidor, cool old photos of famous Americans who lit up here, and a live stogie-rolling demonstration. You can also buy Cuba's best cigars, which is preferable to purchasing cheap imitations disguised as expensive Cohibas on the street.
