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.