H. Upmann Sir Winston

The H. Upmann Sir Winston is one of the great Churchill-format cigars in the Habanos portfolio — a stately 178mm smoke with a 47 ring gauge that demands time and rewards it generously. Named in honour of Britain's most celebrated cigar aficionado, this medium-bodied Cuban delivers nearly two hours of layered complexity, progressing from cedar and cream through leather and espresso to a long, sweet finish.

About H. Upmann Cigars

Founded in Havana in 1844 by German banker Hermann Dietrich Upmann, H. Upmann is one of Cuba's oldest and most distinguished cigar houses. Upmann arrived in Cuba to expand his family's banking interests but became captivated by the tobacco industry, purchasing a factory and producing cigars under his own name. The brand is credited with introducing the cedar cigar box — a practice that became the global standard — and with creating some of the most refined blends in the Habanos portfolio. Today H. Upmann is revered for elegance and consistency across formats from the compact Half Corona to the stately Sir Winston.

Tasting Notes of H. Upmann Sir Winston

The Sir Winston is a long, evolving smoke that builds steadily in complexity across nearly two hours.

- Pre-light: Rich cedar, dried fruit and a subtle earthy sweetness from the wrapper.

- First Third: Cedar, cream and toasted bread — measured and smooth, with light spice on the retrohale.

- Second Third: Leather, espresso and dark wood emerge. The body builds to medium with growing depth and complexity.

- Final Third: A sweetness develops alongside lingering wood and spice — the finish is long and deeply satisfying.

- Overall: Medium-bodied, rich and stately — one of the finest Churchill-format cigars available.

English Market Selection.

Free UK delivery for purchases over £50.

Explore more H. Upmann cigars: H. Upmann No. 2 | H. Upmann Magnum 50

Fun Facts About H. Upmann Sir Winston

Winston Churchill was one of history's most famous cigar smokers — reportedly smoking up to ten cigars a day, favouring large-format Cuban cigars throughout his life.

The Churchill vitola format was named after him by the Romeo y Julieta brand, whose factory he visited. H. Upmann later named their own Churchill-format cigar in his honour.

At 178mm, the Sir Winston is one of the longest cigars in the H. Upmann regular production range.

FAQ About H. Upmann Sir Winston

How strong is the H. Upmann Sir Winston?
Medium-bodied — rich and complex without being overpowering. Better suited to experienced smokers given its length and intensity.

How long does it take to smoke?
Approximately 105 minutes — nearly two hours at a relaxed pace.

Is it good value for a premium Cuban?
At £23 per stick it represents strong value for a Churchill-format Havana of this quality and smoke time.

What does EMS mean?
English Market Selection — confirming the cigars arrived via the official Habanos UK importer and passed additional authenticity and condition checks.