For the first time in 50 years, Americans can legally get their hands on Cuban cigars. Here, a beginner's guide to finding the best stogie.

Story by Richard Morgan |Rhapsody, December 2016

La Casa del Habano in Havana's Miramar neighborhood is nicknamed Quinta Avenida—Fifth Avenue—for good reason. It's essentially the Tiffany's of tobacco: a marble-tiled smoking room with plush armchairs, an immense walk-in humidor, and a roaming peacock.

Carlos Robaina has been tending the store for nearly a decade. He is as close to tobacco royalty as it gets. His father, Alejandro Robaina, the most prominent tobacco titan in the world, received a medal in the 1990s from Fidel Castro that acknowledged him to be the country's best grower; his son, Hirochi Robaina, now runs the plantation that has been in their family since 1845.

But here at the Miramar shop's restaurant—the only cigar-shop restaurant in Havana—over cortaditos (Cuban espressos) that taste as rich and earthy as the smoke in the air, Robaina laughs when a visitor asks which cigar is best. “Which wine is best?" he asks. “Do not choose it. Let it choose you."

Choices now abound for American tobacco lovers. Cuban cigars have always been freely available in London, Rome, Shanghai, and anywhere that didn't have an embargo against Cuban goods, but they have attained legendary status for Americans—not only for their greatness, but for their forbidden greatness.

Now, with commercial flights from America landing in Havana for the first time in half a century, Cuban cigars are, well, catching fire. In October, the Obama administration lifted the five-decade-long trade ban on cigars, allowing Americans to purchase as many as they want as long as they are for personal consumption. This will no doubt spur even more travel to the country. Next year's annual Habano Cigar Festival, from February 25 to March 4, is expected to be record-setting.

“Like your vacation, a cigar is an experience that begins to end the moment you start it. Until you try it again."

As for picking the cigars themselves, there are two main approaches, one for shop purchases and one for factory purchases. According to Richard Carleton Hacker, author of The Ultimate Cigar Book, when buying a box in a shop, it's always best to check the cigars' shade and the degree to which the tobacco is all the same color. The idea is not to favor dark over light—that's a matter of personal taste—but rather that the tobacco in the box is consistent; a mixed box is a poorly made box. And on individual cigars, it's important to check the wrapper for tears, holes, or dark spots; damaged wrappers will hinder the smoking experience.

In factories, on the other hand, Hacker says, “you can have the experience of driving your Mercedes right off the assembly line in Stuttgart." Cuban cigars are hand-rolled, and the rollers are rated on their skill level; grade-seven rollers are the best, able to roll figurados—cigars in complicated shapes. While it's rude to ask a roller directly what his or her grade is, Hacker advises asking the factory manager to point out who the sevens are.

Back in the Miramar shop, Carlos Robaina isn't discussing color, shape, grade, or even price. Strolling through the humidor, he waves at his cache of tobacco. “You can buy it, but you cannot have it," he says. “These are not cigars. This is Cuba. Like your vacation, a cigar is an experience that begins to end the moment you start it." He smiles. “Until you try it again."