H. Upmann Cigars: The Complete Guide to the Banker's Havana

By Michel Besson, Fine Cigars Club

Few cigar brands can claim to be older than H. Upmann, and none has a stranger origin story. It was created not by a tobacco grower or a cigar roller, but by a German banker who loved Havana cigars so much that he began giving them to his clients — and accidentally founded one of the most enduring names in the history of tobacco. From that 1844 beginning to a Cold War intrigue involving President Kennedy and 1,200 cigars, from the medals still printed inside every box to the fact that this very factory gave birth to the Montecristo brand, H. Upmann's story is one of the richest in the cigar world. This guide covers the history, what defines the Upmann taste, the range we stock, how to choose, and the questions smokers most often ask.

The History of H. Upmann

In 1843, a young German named Hermann Dietrich Upmann arrived in Havana. He had been sent to look into business affairs, but — the story goes — a fellow traveller on the voyage over had convinced him that the real opportunity lay in Cuban tobacco. Upmann agreed. Rather than return to Germany, he stayed, learned the cigar trade, bought a local factory, and in 1844 registered the brand that still bears his name.

What makes the founding unusual is that Upmann was, first and foremost, a banker. He and his brother ran the Upmann banking house in Havana, and the cigars began as an elegant piece of client relations: boxes of fine Havanas, stamped with the bank's name, sent to favoured customers and business contacts. The cigars proved more popular than anyone expected. What started as a promotional side project became a business in its own right — and by the turn of the century, H. Upmann was making cigars in more than 200 different sizes and selling many millions a year.

The quality was recognised early and often. Between 1862 and 1893, H. Upmann won seven gold medals at international exhibitions — and those medals, along with Hermann Upmann's own signature, are lithographed inside the lid of every box to this day. It is one of the most distinctive pieces of packaging in the cigar world, and a direct link to the brand's nineteenth-century glory.

The 1922 collapse and the British rescue

The bank and the cigar company ran side by side until 1922, when disaster struck. Speculation — in German currency and Mexican oil, depending on which account you read — brought the Upmann banking house down, and the cigar business fell with it. The brand that had seemed unassailable was suddenly bankrupt.

It was a British firm that saved it. J. Frankau & Co., which had long served as H. Upmann's UK agent, stepped in and acquired the cigar business, and by 1925 the factory was making cigars again. (That British connection runs deep in Upmann's story — and it is the same house, Hunters & Frankau, that remains the sole official distributor of Cuban cigars in the UK today.)

The Montecristo connection — the factory that birthed a legend

In 1935 the brand changed hands again, and this is where H. Upmann's history becomes genuinely remarkable. The company was sold to Menéndez, García y Cía — the very people who, that same era, created Montecristo. For years, Montecristo cigars were rolled inside the H. Upmann factory. In other words, the world's most famous cigar brand was born in the home of one of its oldest. The two have been intertwined ever since.

To mark H. Upmann's centenary, the new owners opened a grand new factory in 1944. Today that factory is officially known as the José Martí factory — and it remains one of the most important addresses in the cigar world: the H. Upmann factory (José Martí) in Havana rolls H. Upmann, Montecristo, and select Cohiba cigars. Three of Cuba's most storied brands, made under one roof, all from Vuelta Abajo tobacco. If you enjoy the Upmann story, our Montecristo guide tells the other half of it — and our Cohiba guide covers the third.

The JFK story — 1,200 cigars and an embargo

No history of H. Upmann is complete without its most famous smoker. President John F. Kennedy was devoted to the machine-made Petit Upmann. In February 1962, with the Cuban trade embargo about to come into force, Kennedy dispatched his press secretary, Pierre Salinger, to buy up every H. Upmann he could find in Washington. Salinger returned the next morning with around 1,200 Petit Upmanns — and only then did the President sign the order that would make importing Cuban cigars illegal for Americans. It is one of the great cigar anecdotes, and it happens to be true.

After the revolution and nationalisation, the Menéndez-García family left Cuba and eventually established a non-Cuban H. Upmann in the Dominican Republic (made today by Altadis). But the original — the Havana H. Upmann, made in Cuba from Vuelta Abajo tobacco — continues, and that is the cigar this guide is about, and the one we stock.

What Defines the H. Upmann Taste

H. Upmann is one of the classic light-to-medium-bodied Havana brands — a cigar of finesse rather than force. Where a Partagás is bold and earthy or a Ramón Allones rich and spicy — and a Romeo y Julieta sits balanced in the middle — the Upmann profile is elegant and refined: cedar, toasted bread, light coffee, a gentle nuttiness and a soft, natural sweetness, often with a delicate spice on the retrohale. It is a wonderfully easy-drinking style — approachable enough for a newer smoker, but with enough nuance and aromatic detail to reward an experienced palate.

That elegance is exactly why it makes such a fine daytime or morning cigar. It doesn't overwhelm, it pairs beautifully with coffee, and it showcases the aromatic, fragrant side of Cuban tobacco rather than its power. For many aficionados, a well-aged H. Upmann is one of the most quietly rewarding cigars in the Havana catalogue.

The H. Upmann Range We Stock

We carry a focused selection of genuine Cuban H. Upmann, chosen to represent the brand's classic elegance across two very different formats.

H. Upmann Connoisseur No. 2

A modern classic and, for many, the definitive contemporary Upmann. The Connoisseur No. 2 is a robusto-style vitola that shows the brand at its best: creamy and refined, with honey, roasted nuts, cedar and a gentle spice. It's a slightly richer, more substantial take on the Upmann style while staying firmly in the elegant camp — an ideal introduction to the brand, and a cigar that has become a favourite among Havana enthusiasts for its balance and quality.

H. Upmann Regalias

For a shorter, more traditional smoke, the Regalias delivers the classic Upmann flavours — cedar, toast, light coffee and a soft sweetness — in a handy petit corona size. It's perfect for a shorter smoking window, a coffee break or a first cigar of the day, offering the brand's signature elegance without a long time commitment. It's also the cigar pictured at the top of this guide — look closely at the inside of the lid and you'll see those seven gold medals.

H. Upmann Magnum 52 Year of the Tiger 2022 (Collector's Edition)

For the collector, the Magnum 52 Year of the Tiger 2022 is a rare and beautiful thing. Released as part of Habanos's celebrated Chinese zodiac series to mark the Year of the Tiger, this limited edition presents the Magnum 52 vitola in a striking red-and-gold lacquered box of 18 — as much a display piece as a smoke. It's a chance to own a genuine piece of modern Havana collecting, and a reminder that beneath its everyday elegance, H. Upmann still commands the prestige of a top-tier Cuban house. Available in our limited release range.

You can browse the full range on our H. Upmann collection page.

Which H. Upmann Should You Choose?

If you're new to the brand — start with the Connoisseur No. 2. It's the fullest expression of the modern Upmann style, beautifully balanced, and the cigar most likely to show you what the brand is about.

If you want a shorter smoke — the Regalias gives you the classic Upmann character in a petit corona, ideal when you have less time or want a lighter morning cigar.

If you're a collector — the Magnum 52 Year of the Tiger 2022 limited edition is a rare, beautifully presented piece from Habanos's zodiac series, and a genuine investment-grade Havana for the display cabinet.

If you love elegant, aromatic Cubans — H. Upmann as a whole is for you. If you already enjoy the refined side of Havana (a Hoyo de Monterrey Epicure, say, or a lighter Romeo y Julieta), Upmann sits naturally alongside them. Compare the Hoyo de Monterrey Epicure No. 2 for another elegant Cuban in a similar register.

If you prefer power — H. Upmann may feel too gentle. A Partagás Serie D No. 4 or a full-bodied Ramón Allones would suit you better — though many smokers keep an Upmann in the humidor precisely for the mornings when they don't want power.

How to Spot a Genuine Cuban H. Upmann

As one of the oldest and most respected Havana brands, H. Upmann is also counterfeited. A few pointers:

• Buy from a reputable source. Genuine Cuban cigars reach the UK through the official distributor, Hunters & Frankau, and carry the English Market Selection (EMS) mark. That's your first assurance of authenticity and proper storage.
• Check the box. Genuine boxes carry the Cuban government warranty seal, the "Habanos s.a." and "Hecho en Cuba / Totalmente a mano" markings, a factory code and date stamp, and — distinctive to Upmann — the lithographed gold medals and Hermann Upmann's signature inside the lid.
• Look at the band and construction. Genuine Havanas are impeccably rolled with a smooth draw and even burn; poor construction, a spongy feel or a crude band are warning signs.

We source all our Cuban H. Upmann through Hunters & Frankau, so every cigar is genuine English Market Selection stock.

Frequently Asked Questions

Who founded H. Upmann, and when? H. Upmann was founded in 1844 by Hermann Dietrich Upmann, a German banker who had settled in Havana. He originally had the cigars made as promotional gifts for clients of his banking house; they proved so popular that the cigar brand became a business in its own right and remains one of the oldest in the world.

Why are there gold medals on the H. Upmann box? Between 1862 and 1893, H. Upmann won seven gold medals at international exhibitions. Those medals — along with Hermann Upmann's signature — are lithographed inside the lid of every box to this day, a direct link to the brand's nineteenth-century reputation for quality.

What is the connection between H. Upmann and Montecristo? In 1935 the H. Upmann brand and factory were bought by Menéndez, García y Cía, the creators of Montecristo. Montecristo cigars were rolled in the H. Upmann factory, so the two brands share a home and a history. The factory — now called the José Martí factory — still produces both today.

Is it true President Kennedy stockpiled H. Upmann cigars? Yes. President John F. Kennedy favoured the Petit Upmann. In February 1962, the night before signing the Cuban trade embargo, he had his press secretary Pierre Salinger buy around 1,200 of them from Washington tobacconists — securing his supply just before importing Cuban cigars became illegal for Americans.

Is H. Upmann a strong cigar? No — H. Upmann is one of the classic light-to-medium-bodied Havana brands. It's elegant and refined, with cedar, toasted bread, light coffee, nuts and a soft sweetness, which makes it a superb daytime cigar and very approachable for newer smokers, while still rewarding experienced palates.

Are there Cuban and non-Cuban versions of H. Upmann? Yes. After nationalisation, the Menéndez-García family established a non-Cuban H. Upmann, made today in the Dominican Republic by Altadis for some markets. The original Cuban H. Upmann is made in Havana from Vuelta Abajo tobacco — that is the version we stock, sourced as genuine English Market Selection through Hunters & Frankau.

Explore our full range of genuine Cuban H. Upmann cigars, or read our companion Montecristo and Cohiba guides.

Fine Cigars Club is a UK retailer of premium cigars. All Cuban cigars we sell are genuine Havanas supplied through official UK channels.