On the Cigar Trail in Cuba – Part I

Havana, Cuba -Prompted by thawing relations, an American cigar lover goes to Cuba to find one of the best.

Walking along the gritty, darkening streets of Havana, I felt a sense of foreboding wash over me. A few paces ahead was a stranger. Jorge, he called himself, a young street hustler I had just met at a taxi stand outside the Hotel Capri. Jorge was dressed decidedly urban: an oversize San Diego Padres jersey, baggy denim shorts and Adidas shell-toe sneakers. Jorge was also charming, and through broken English he had enticed me from the touristy environs of downtown into what was eerily morphing into a barren, crumbling neighborhood of sagging rowhouses. The object of seduction: a box of Habanos, or hand-rolled cigars.

It was my first night in Havana, a trip prompted by thawing relations between the United States and Cuba. A few months before, in late December, President Obama had ordered the restoration of full diplomatic relations, setting in motion plans to open an embassy in Havana for the first time in more than a half-century.

As nightfall quickened, my sense of vulnerability was heightened by the clop-clop of my sandals on the cobblestone streets. It seemed too late to start chastising myself for being a naïve American tourist dumb enough to be coaxed into the night for a few stogies. Ahead of me, Jorge, looking more sinister by the second, waved me on. Moving deeper into the Havana ’hood, I was, it seemed, at God’s mercy now — in a country noted, incidentally, for its dearth of churches and religion (despite the island’s warm reception of Pope Francis recently).


Mamino Gonzalez Gomez, 79, demonstrates his cigar-rolling technique. Credit: Todd Heisler/The New York Times

Soon we reached a dilapidated brick building in the central neighborhood of Vedado. “Here, my friend!” Jorge said. “Good price here on Montecristo, and Cohiba, too!”

Jorge rang a doorbell. A window two flights up opened, and keys dropped to the ground. He led me up a dim stairwell to an open apartment door, where we were greeted by a shirtless guy and an elderly woman who spirited me into a back room. And there it was on a wooden table, its lid majestically open: a box of Cuban Montecristo No. 2s.

For the uninitiated, let me shed light on this treasure trove. Celebrated for its complex blend of creamy and spicy aromas, the Montecristo No. 2 is arguably the Cadillac of Cuban cigars; highly prized among aficionados and a rare find for the likes of me or any other occasional cigar-smoking American.

I stepped over to admire the 25 torpedo-shaped beauties, light brown in hue and just over six inches long, each adorned with a chocolate-brown band emblazoned with a white sword insignia. Montecristo No. 2, the name inspired by the Alexandre Dumas novel, had long been among my favorites, rare enough that I couldn’t remember the last time I smoked one.

“Gracias,” I told the woman, who shot me a weary smile as she wrapped my bounty in newspaper. I knew the price, 80 CUC (convertible Cuban pesos, priced to the American dollar), would spark envy in buddies back home accustomed to paying upward of $350 on the black market for a box of these gems. “You happy, my friend?” Jorge asked. I shook his hand, then hugged him as if he were family.

Fifty-three years have passed since President John F. Kennedy enacted the Cuban trade embargo, ushering in a Dark Ages for American cigar enthusiasts. What’s less known, though, is that before imposing these historic sanctions on all Cuban products, the president called his press secretary at the time, Pierre Salinger, and asked him to secure “a lot of cigars,” Mr. Salinger recounted in 1992 in Cigar Aficionado magazine. As it happened, it wasn’t until the following morning, when Mr. Salinger informed the president that he had, in fact, scored 1,200 petite H. Upmanns (named after Herman Upmann, a German banker who opened a branch in Havana in the mid-1800s to send cigars home to Europe), that Kennedy signed the decree.

For the average American cigar lover, Cuban smokes have remained mostly the rare indulgence; a celebratory spoil procured through mysterious back channels and offered when babies or businesses are born. Yet suddenly, the restoration of diplomatic relations with Cuba last July brought with it the prospect of a cigar renaissance; opening a path for ordinary Americans to visit and bring back, for now at least, $100 worth of Cuban cigars from tobacco’s Holy Grail.

Continue (On the Cigar Trail in Cuba Part II)

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