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).
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.
The eased sanctions put me in the mood to explore Cuba’s cigar culture, including the Alejandro Robaina Tobacco Plantation, arguably the most famous tobacco farm in the world. The home of the late farmer Alejandro Robaina, known as the face of the Cuban cigar, Robaina is tucked away in the town of San Luis in the Pinar del Río province, the most western section of Cuba. Founded in 1845, the farm is known for its robust yields of high-quality wrapper leaves; so impressive, in fact, that in the early 1980s Fidel Castro — a cigar-smoking Cohiba man himself — branded these cigars with the Robaina family name, the only Habanos to boast such a distinction.
While Cuba can’t lay claim as the birthplace of cigars (historians give those bragging rights to farms in Guatemala), the island reigns as the world’s best producer of quality leaves, as celebrated as Napa and Bordeaux are by wine lovers.
Traveling to Cuba is not generally the smoothest affair. I enjoyed the advantage of the Cuban embassy granting me permission to document this adventure as an official journalist. Most American cigar aficionados wanting to visit might find getting there quite difficult, since the law still does not allow Americans to travel to Cuba for tourism, but rather only for a dozen approved categories, which include religious and educational activities, professional research and humanitarian projects.
For lodging in Havana I chose the Hotel Capri, a block from the Hotel Nacional, a favorite haunt of the notorious mobster Meyer Lansky, and near other famous cigar shops and rolling factories, as well as nightclubs flowing with Havana Club rum and Afro-Cuban music. The Capri, operated by the NH Hotel Group of Spain, also has Internet access, although the service was so spotty that I moved for my final night to a quieter, family-owned bed-and-breakfast, which turned out, in fact, to be decidedly lacking Internet access and other luxuries.
Cigar smokers, actually smokers in general, enjoy rare freedom in Cuba, a carte blanche to light up in virtually any restaurant or bar, generally unheard of these days in North America and Europe. On my first evening, after a delicious seafood risotto on the balcony at the Café Laurent, a penthouse paladar (or privately owned restaurant) overlooking the Malecón, my waiter glanced at my newly acquired Montecristo No. 2 resting on the table. I planned to smoke it during a stroll afterward. Yet moments later, my cigar was cut — thanks to my hospitable waiter — and with its tip aglow, I gazed out at the Havana skyline. The view included the city’s tallest building, the state-owned Focsa, a towering commercial-residential structure, which at its base included a gigantic swimming pool with no water on this sweltering night.
I savored the creamy aroma of my cigar, or puros, marveling at the perfection of the moment: the city lights and the rumba music wafting up from the streets. Even the non-cigar smoker must concede that a kind of Habanos romance swirls across this island. Cubans cherish cigars, literally. The works of the late Cuban poet Heberto Padilla have been compared to a great cigar: balanced, full flavored and serene. In the late 1960s, before Fidel Castro’s regime imprisoned and tortured the poet for criticizing Castro’s government, and before such intellectuals as Susan Sontag and Jean-Paul Sartre successfully campaigned for his release, Mr. Padilla had written, rather presciently: “General, I can’t destroy your fleets or your tanks/and I don’t know how long this war will last/but every night one of your orders dies without being followed/and, undefeated, one of my songs survives.”
Such lyricism inspired the Padilla 1968 Golden Bear cigar, an earthy-flavored tribute to the poet. It’s called the 1968 Series because that’s the year Mr. Padilla published the anthology “Fuera del Juego” (“Out of the Game”), which ultimately got him locked up for “having plotted against the powers of the state.” Cigar novices might mistake this hard-to-find cigar band’s red and gold illustration for a crown, but aficionados know it’s actually the nib of the poet’s fountain pen.
Cigar nostalgia abounds in Cuba, and I encountered few more eager to share it than Michael Phillips, a Briton who moved to Havana some 25 years ago to teach English. He is a devoted member of the city’s Cigar Aficionado Club, whose members — foreign diplomats and businessmen — meet monthly for dinner, cigars and conversation. Sitting in the spacious living room of his apartment in the upscale Miramar neighborhood, where most of the city’s top government officials reside, Mr. Phillips poured Cognac and held out a tray of unbanded cigars, from short coronas to lengthier Churchills, tan Habanos to darker Maduros. He grinned at my selection, pyramid-shaped and walnut in color.
“Don’t ask me where it came from,” he said mischievously, “because I cannot tell you.”
After some prodding, Mr. Phillips explained his suspiciously bandless cigar menu: “The rollers in the factory have a quota, but many of the women find a way to sneak a few extras out. So they roll for eight hours in the factory, and then come home and roll for another two hours.”
He lit up, drew from his cigar, and watched the plume rise. “There was one girl who worked at the Romeo y Julieta factory; she was pregnant for three years!” He chuckled at such clever smuggling. “But yes, these are as good as the ones from the factory.”
Cigar enthusiasts are a discriminating bunch, yet most agree that Cuba is blessed with a unique combination of sun, soil and moisture — coupled with a rich history of hand-rolling — that makes for the world’s most flavorful cigars, Mr. Phillips said. If there was a dark period, it occurred during the Communist revolution as some of Cuba’s most talented growers fled and set up operations in countries such as the Dominican Republic, Ecuador, Honduras and Nicaragua. While an infusion of Soviet cash helped to prop up Cuba’s cigar industry, competition over the next several decades from its new foreign rivals — along with some bad crop years and a dismal foray into tobacco hybridization — diminished its product. The complaints, ranging from poor flavor to shoddy construction, dragged Cuban cigars down in Cigar Aficionado magazine’s vaunted annual rankings. From 1998 to 2005, Cuban cigars never scored above an average 88 on a 100-point scale, compared with its typical 90-plus average in years beforehand.
Such history is always surfacing here, a collision of old glory and modern reality that infuses even its architecture. On Tenerife Street in central Havana, for instance, is a former factory that was once a major production house and storage facility for cigars. Decades ago, the owners fled and passed the building down to remaining family members. A few years ago, though, city officials took note that there was, once again, a family living in the factory, and have since taken over the rest of it and renovated it with apartments. Former factory workers, who once lived in poor conditions, now reside free of charge in modern living quarters.
In Cuba, those smoking the finest cigars tend to be visitors like me, expats like Mr. Phillips, senior government officials and international business people. Most Cubans living on a state salary of less than $20 a month can’t afford hand-rolled cigars of export quality. Cubans do smoke local cigars, but they are not good quality and cost about a nickel in American currency and can be fodder for swindling undiscerning tourists.
The country’s economic hardship became clearer on a sunny morning during a drive to the Robaina plantation. I was traveling with a translator and two of her friends, erstwhile guides. For the two-hour trip, my guides had wisely traded in the hulking 1950s Chevrolet taxi we’d used in the city for a late-model Pontiac rental. As dense, boisterous Havana receded and the urban landscape turned into rolling green countryside, I saw another side of Cuba: rural and scattered with clapboard shanties and mules, donkeys and chickens, especially as we headed deeper into the region of Pinar del Río. There, one is reminded of the island’s poverty, even if it’s offset by a tight-knit culture where the sound of laughter and chatter envelops fruit stands displaying bananas and papaya. At one roadside stop, I treated myself to a 10-cent cigar and a cookie stuffed with guava jam.
Tucked away on a narrow dirt road, the farm is easy for tourists to miss but for a modest hand-painted sign “Finca El Pinar Robaina” posted off the main one-lane drag. A mile or so along the road, the landscape turns into a bright green panorama of tobacco plants rustling in the breeze and stretching out infinitely in well-manicured rows. During growing season, from October through February, the plants can grow as high as 50 inches.
Yanelis Delgado, a longtime neighbor and family friend in her early 40s, greeted me and began spinning yarns about Alejandro Robaina, the plantation’s founder, who died at 91 in 2010. For the next couple of hours, we walked around the 170-year-old property and Ms. Delgado shared stories, including how Mr. Robaina, who smoked his first cigar at age 10, took the reins of the operation after his father died in 1950. On a terrace adorned with flags representing the countries of visitors to the farm over the years is a life-size carving of Mr. Robaina sitting in a rocker gazing across the field. The memorabilia on display includes photos of world leaders and celebrity guests at the farm, and a handwritten note of encouragement (translated: “Hirochi, you are my future. Don’t disappoint me”) from Alejandro to his grandson, Hirochi Robaina, who now owns the farm.
As one of Cuba’s few independent growers — most farms belong to cooperatives — the Robaina plantation became known for his growing techniques, which became synonymous with such premium brands as Cohiba and Hoyo de Monterrey. His tight relations with senior government officials — including both Cuban presidents Fidel Castro and his brother Raúl — led to the government creating one of the island’s 27 brands in his honor. To be sure, the brand is not as renowned as, say, Partagás and Romeo y Julieta, and cigar smokers have in recent years criticized the company for inconsistent quality as it struggled to meet rising demand that came from Castro’s homage to the farm.
Cigarmaking is intricate, and success is governed mostly by timing, temperature and the artistry of human hands. It takes nearly two years for a cigar to move from nursery to rolling factory, Ms. Delgado explained. In the nursery, seeds are planted for germination and then a month later replanted as seedlings. In the roughly 45 days after the replanting, growers irrigate and treat the plants for pests. Once the leaves are brought into the drying or curing barn, they are strung with thread and hung from high ceilings. “It’s like a cathedral for tobacco,” Ms. Delgado said of the wooden barn, sun-bleached white with red shutters.
The drying process lasts 50 days, during which the leaves change from green to yellow to brown. The thread is cut and the leaves are bundled, placed in piles and covered with a net for some 40 days at 100 degrees or more to spur fermentation, which determines the concentration of nicotine in leaves, flavor, aroma and texture. In the curing barn I watched a farm veteran lay out leaves and, within minutes, construct a flawless cigar, which he handed to me. The farm sells 90 percent of its product to the Cuban state-run cigar company, S.A. Habanos.
Serious cigar smokers wax poetic with the language of wine aficionados, referring to a cigar’s flavor as “spicy” or “creamy” with hints of “honey,” “cocoa” and “cinnamon.” Cuba’s tobacco farmers take fierce pride in producing the most flavorful cigars in the world. Their nemesis is the expanding market not only for Cuban knockoffs but also for iconic Cuban brands whose leaves and labor are actually from other parts of the world, partly as a result of fleeing growers restarting their businesses elsewhere.
For instance, the premium brand Cohiba, created exclusively in the mid-1960s for Castro and other senior government officials, has been embroiled in litigation for years as Habanos S.A. has contested the right of an American firm, the General Cigar Company, which manufactures Cohibas in the Dominican Republic, to sell under the Cohiba brand. As one senior manager at TabaCuba, the state agency that runs Cuba’s tobacco production and research, told me: “A Cuban cigar must be made with Cuban sun, Cuban soil, with Cuban hands. If not, there are no properties that make it what it claims to be.”
It’s estimated that some five to eight million Cuban cigars reach Americans each year by way of countries like Canada, Switzerland, Australia and Mexico. Most experts agree that eased trade sanctions are far from opening a retail gateway between the United States and Cuba. It will take years, they say, for sellers to clear the byzantine network of international politics, trademark restrictions and F.D.A. regulations. When Cuban cigars finally do arrive abundantly — and legally — on American soil, most experts figure it will be through the Casa del Habano, Cuba’s state-owned chain of cigar boutiques, which already has some 130 stores worldwide.
Cuban cigar culture, of course, can’t be exported. On my final day in Havana I came across the Hotel Conde de Villanueva, billed as the world’s only hostel dedicated to cigars. In the atrium, peacocks strutted as a “torcedor” rolled cigars for guests. Each of the nine guest rooms is named after a tobacco farm. A gorgeously restored 18th-century mansion adorned with stained-glass windows, the hotel also has an excellent cigar shop, plus an intimate smokers lounge. Gracing one wall are photographs of celebrities smoking cigars (among them, Demi Moore, Denzel Washington, Groucho Marx, Ernest Hemingway, Winston Churchill and Sigmund Freud). The hotel is surrounded by shops selling everything from chocolate to perfume.
The atmosphere didn’t feel exactly authentic, so I walked a couple blocks away, deeper into Old Havana, and found a quiet seat beneath a canopied outdoor bar. It was a perfect spot to relax, to enjoy the distant sound of rumba and the view of vintage cars moving along the streets. I ordered a mojito. And then I lit my last cigar in Cuba.
IF YOU GO TO CUBA
Where to Eat
Café Laurent (Calle M No. 257, between 19 and 21, Vedado, Havana, cafelaurent.ueuo.com) is a stylish family-run paladar popular for its penthouse views and Spanish-themed menu. Expect to pay about 20 American dollars per person for dinner.
Siá Kará Café (Calle Industria No. 502, www.siakaracafe.com) offers reasonably priced Cuban cuisine in the heart of Old Havana. It is also known for live music.
Nazdarovie (No. 25 Malecón, nazdarovie-havana.com) is a retro-styled Soviet restaurant and bar with live music; overlooks the sea.
Mamaine (Calle L No. 206, between 15 and 17, Havana) is an artsy, intimate cafe known for a breakfast menu that includes tortillas and fresh mango juice.
Where to Go
Alejandro Robaina Tobacco Plantation in the Vuelta Abajo region, southwest of the city of Pinar del Río. The farm offers daily tours, but it is best to have your hotel arrange a guide for this all-day trip into a rural area: 53-48-79-74-70.
Old Partagás Factory and Cigar Shop (Calle Industria No. 520, Havana) is 170 years old and perhaps the island’s best-known factory. Its production recently moved to the El Rey del Mundo Factory nearby but the retail store is still open, and sells a variety of brands made at the factory, from Bolivar to La Gloria Cubana.
La Casa del Habano (5ta Avenida y Calle 16, Miramar, Playa, Havana, lacasadelhabano.com) is among the premium cigar stores and lounges in Cuba and several other countries authorized to sell Habanos S.A. brands. The United States is the only country to which Habanos S.A. does not sell cigars.
Where to Stay
Hotel Capri (Calle 21 between calle N and O, Vedado, nh-hotels.com/hotel/nh-capri-la-habana), a modern high-rise in the heart of central Havana, offers easy access to popular restaurants, nightclubs and cultural sights, including the famous Hotel Nacional, a block away. Single rooms run about $130.
A Few Top Brands
Some popular Cuban cigars, $10 to $20 each.
Partagás Serie D No. 4 A full-bodied robusto with a woody and spicy aroma.
H. Upmann Royal Robusto Known for its full coffee bean flavor and oak finish.
Montecristo No. 2 Medium to full with creamy and spicy notes.
Bolivar Royal Corona Richly complex with hints of chocolate and coffee.
Cohiba Siglo III Vanilla, leathery flavored and best paired with sweet desserts.
Vegas Robaina Don Alejandro Medium bodied with sweet and woody undertones.