Product Presentation: Box of 25
First Third
The Sir Winston opens with remarkable grace. Cedar greets you immediately—not the sharp pencil-shaving kind, but warm, aged wood like opening an antique humidor. Floral notes dance at the edges, delicate and unexpected. A whisper of graham cracker sweetness develops on the retrohale. The draw is perfect, offering just enough resistance to slow you down and make you pay attention. This is a conversation starter, not a sprint.
Mid-Section
Here's where the magic happens. The cedar evolves into something darker, almost resinous, while dark chocolate and marzipan enter the palate. Roasted coffee adds depth, and cream coats every surface. Leather appears, supple rather than heavy. The body remains in mild-to-medium territory but gains significant complexity. The long format allows each component time to develop and interact—this is the Sir Winston's greatest strength.
Final Third
The final act of this 90-minute experience brings gentle intensity. The earth notes that were absent early on now make their presence felt, joining the cedar and leather. Floral notes return briefly before giving way to a warm, sweet finish. Coffee lingers on the palate alongside marzipan and aged wood. The cigar ends as gracefully as it began—composed, elegant, and deeply satisfying.
| Feature | Details |
| Primary | Aged cedar, dark chocolate, marzipan |
| Secondary | Roasted coffee, cream, floral notes, leather |
| Finish | Long and sweet with lingering coffee and cedar |
Founded in 1844 by German banker Herman Upmann, this marca began as a way to send cigars back to Europe. The bank eventually failed, but the cigars endured—a testament to where true value lies. The Sir Winston Churchill format is named after the most famous cigar smoker in history, whose preference for the generous Julieta format helped establish the Churchill as one of the most popular vitola categories worldwide.
15-45 Days Standard Shipping.
H. Upmann Sir Winston
$650.00
The H. Upmann Sir Winston is a Julieta No. 2 (Churchill) format Cuban cigar measuring 178 mm (7") with a 47 ring gauge, presented in boxes of 25. Named after Britain's most famous cigar smoker, it is the flagship vitola of the H. Upmann brand and one of the most respected Churchills in the Habanos catalogue.
Suited to experienced smokers seeking a grand-format Cuban with H. Upmann's signature elegance, this medium-bodied cigar delivers a refined, multi-layered experience over a generous 90-minute session.
The generous Churchill format gives the blend ample room to develop, rewarding patient smokers with evolving complexity. Construction passes multiple quality inspections, meeting the exacting Habanos S.A. standard. The overall character is smooth and distinguished — cedar, cream, and subtle spice form the foundation, with coffee, leather, and earthy notes building depth as the cigar progresses. The 47 ring gauge maintains a cool, elegant draw throughout the extended session, keeping the profile refined and composed.
Every H. Upmann Sir Winston from Cuban Cigars For Sale is sourced through authorized Habanos channels, ensuring authenticity and proper storage. Shipped worldwide with humidity-sealed packaging.
| Brand | H. Upmann |
| Ring Gauge | 47 |
| Length | 178 mm (7.0") |
| Strength | Mild to Medium |
| Size | Julieta No. 2 |
| Vitola | Julieta No. 2 |
| Primary | Aged cedar, dark chocolate, marzipan |
| Secondary | Roasted coffee, cream, floral notes, leather |
| Finish | Long and sweet with lingering coffee and cedar |
3 reviews
Bought my first box of Sir Winstons last year. My advice: let them rest in your humidor for at least three months before smoking. The ones I tried right away were good but a bit tight on the draw. After resting, the fourth stick I lit was phenomenal — open, flavourful, with a perfect burn line and layers of cedar, cocoa, and spice. A truly premium cigar experience that earns its spot among the best Cuban Churchills available today.
I've been working my way through the H. Upmann range and saved the Sir Winston for last. It was absolutely worth the wait. Impeccable construction, silky wrapper, and a draw that's perfectly calibrated. The flavour journey is extraordinary — I noted caramel, aged wood, roasted coffee, and leather, all woven together seamlessly. This is the kind of Cuban cigar experience that makes you understand why aficionados travel to Havana. If you want to buy H. Upmann Sir Winston online, just make sure you have a comfortable chair and nowhere to be for a couple of hours.
The H. Upmann Sir Winston is the kind of cigar you clear your schedule for. This is a full-sized Churchill that demands time and attention, and rewards both generously. I smoked mine after a long Sunday lunch — two hours of evolving flavour, from creamy cedar and almond in the opening, through a rich, earthy middle, to a peppery, complex final third that had me genuinely sad when it ended. This is how a premium Cuban Churchill should taste. It gives the Cohiba Esplendidos a real run for the money. Magnificent cigar.
Common questions about H. Upmann Sir Winston
Few artifacts in the world of luxury tobacco capture the imagination quite like the Grand Corona 1492 Humidor. Released to mark a pivotal moment in...
Cigar InfoFor aficionados of Cuban tobacco, the landscape is constantly shifting. While new lines are introduced with regularity, the history of Habanos is...
Cigar InfoFor the discerning aficionado, few subjects evoke as much nostalgia as the discontinuation of a beloved Cuban vitola. Among the many formats that...
