Every Casa del Habano cigar shop in Havana – there are nine in the capital – is its own meticulously stocked humidor. When the Caribbean heat sits heavily on the city, the climate-controlled rooms and their adjoining bars, insulated by sweet-smelling cedar, stay cool. Men loiter at the counters, discussing the innumerable permutations of length, age, and gauge that differentiate the valuable stock. For American visitors to Cuba on one of the cultural immersion programs facilitating tourism (the only way into the country for non-missionaries and non-medical personnel), buying and smoking one of these quality stogies is a matter of course. The question is how to wring the most pleasure from an embargoed experience.
There is not, for the record, such a thing as a "deal" on a Cuban cigar, no matter what vendors might claim. Every cigar – many varieties retail for north of $50 off the island – is a great deal. Still, the best selection is probably a Cohiba Siglo VI, the gem of the Cohiba Siglo line and the smartest $20 a body can spend in Havana. At six inches in length with a 52-ring gauge (meaning 52/64ths of an inch in diameter), this cigar has enough heft to let you know it's not screwing around. Few veins run through the caramel-colored wrapper on a Siglo VI (hilarious, we know) because the workers who hand-roll this tobacco are artists. This cigar packs complex flavors of earth, spice, and creaminess into the smoothest delivery possible. The draw remains even, and, as the Siglo VI burns, the taste increases in complexity.
Every Siglo VI even comes packaged individually in a cedar-lined, yellow-and-black aluminum tube. Every Siglo VI deserves that sort of protection.
Novice cigar smokers might not want to start with a Siglo VI for the same reason that no one with a learner's permit should be driving an Aston Martin. In order to get a frame of reference, toking tourists would be wise to try a few mid-tier cigars on the way up. But even an amateur can taste, feel, and smell that something brilliant goes into every Siglo VI. This is the tobacco equivalent of stepping up from V.S. cognac to X.O.
For an intimate smoking experience, the Hotel Conde de Villanueva offers the perfect atmosphere for a pleasurable smoke. Tucked away on the second floor, the hotel's smoke shop serves strong coffee. Don't order any. Instead, sidle into the tiny bar, where the walls are draped with sporting clubs' flags and the clientele is knowledgeable about booze and tobacco. Paired with an aged rum, such as Havana Club Añejo 15 Años (or even the 7 Años), the Cohiba Siglo VI delivers a glimpse of how Hemingway spent the 1940s and '50s: Filling up on smoke, liquor, and stories.
More information: The only way to travel legally to Cuba is with a so-called "people-to-people" educational-trips operator licensed by the Treasury Department's Office of Foreign Assets Control. There are an increasing number of these groups, but we recommend Insight Cuba, a nonprofit organization with a well-organized staff and deep local knowledge. On the ground, finding a cigar is as easy as waving at a friendly local and miming a puffing motion. Someone will point you in the right direction.