Description
The H. Upmann Sir Winston stands as a towering achievement in the world of Habanos, often whispered about in the same breath as the most legendary vitolas ever rolled. This Julieta No. 2, more commonly known as a Churchill, is the quintessential connoisseur’s choice, offering a medium-bodied profile that balances immense complexity with a refined, gentlemanly restraint. Named in honor of the British statesman and perhaps the world’s most famous cigar enthusiast, the Sir Winston is a masterclass in evolution, transitioning through an olfactory landscape of creamy chocolate, floral sweetness, and toasted butter biscuits. For those who seek a prolonged, transformative smoking experience that lasts between 75 and 90 minutes, this cigar is not merely a product; it is a rite of passage. Crafted with the finest leaves from the Vuelta Abajo region, it represents the pinnacle of the H. Upmann brand’s 180-year legacy of excellence.
Box Features and Packaging Options
| Feature | Box of 25 | Box of 10 |
|---|---|---|
| Cigars per Box | 25 Individual H. Upmann Sir Winston | 10 Individual H. Upmann Sir Winston |
| Packaging Type | Varnished Semi Boîte Nature (SBN) Box | Varnished Wood Box / Dress Box |
| Ideal For | Long-term aging and serious collectors | Sampling or gifting for special occasions |
| Humidity Protection | Cedar lining for optimal maturation | Sealed for freshness and immediate enjoyment |
Cigar Specifications
| Vitola | Julieta No. 2 (Churchill) |
| Length | 178 mm (7 inches) |
| Ring Gauge | 47 |
| Wrapper | Cuba (Vuelta Abajo) |
| Binder | Cuba (Vuelta Abajo) |
| Filler | Cuba (Vuelta Abajo) |
| Strength | Medium |
| Body | Medium to Full-bodied Evolution |
| Smoking Time | 75–90 Minutes |
| Factory | H. Upmann Factory, Havana, Cuba |
| Brand Owner | Habanos S.A. |
Brand Heritage
The story of H. Upmann is one of the most storied in the annals of Cuban tobacco. Founded in 1844 by Hermann Dietrich Upmann, a German banker who traveled to Havana with the dual intent of opening a bank and indulging his passion for cigars, the brand quickly became a symbol of European luxury. Upmann was a visionary; he is credited with being one of the first to use cedar boxes to transport cigars, often gifting them to his banking clients as a mark of prestige. The gold medals that adorn the brand’s “Vista” or box art today are a testament to the numerous awards won by the brand at international exhibitions during the 19th century.
The Sir Winston vitola itself carries a weight of history that few other cigars can claim. While Sir Winston Churchill famously favored many brands, his affinity for the 7-inch by 47 ring gauge format led to this specific size being named in his honor. The H. Upmann Sir Winston is widely considered the most elegant expression of this vitola, capturing the sophisticated, intellectual, and enduring spirit of its namesake. It remains a “white whale” for many collectors, produced in limited quantities due to the scarcity of the high-grade, large-format wrapper leaves required to roll a cigar of this magnitude.
In the modern era, H. Upmann has maintained its position as a “Global Brand” within the Habanos S.A. portfolio. The Sir Winston, in particular, has seen special releases such as the Gran Reserva Cosecha 2011, which utilized tobaccos aged for five years before rolling. This commitment to traditional methods—specifically the Totalmente a Mano (totally handmade) technique using long-filler tobacco—ensures that every Sir Winston provides a consistent, high-luxury experience that honors Hermann Upmann’s original 19th-century vision.
Tasting Profile
First Third – The Opening
The experience begins with an enticing cold draw that offers hints of citrus zest, damp earth, and rich cocoa. Upon lighting, the H. Upmann Sir Winston greets the palate with a remarkably smooth and welcoming introduction. The dominant notes are creamy chocolate and a delicate floral sweetness that dances on the tip of the tongue. Unlike more aggressive Cuban brands, the Sir Winston starts with a “velvet glove” approach, where the smoke is dense and aromatic but never overwhelming. Subtle nuances of vanilla and light cedar begin to emerge, setting a sophisticated stage for the complexity to come.
Second Third – The Heart
As the cigar progresses into the middle third, the body begins to broaden, and the complexity deepens significantly. This is where the H. Upmann DNA truly shines. The floral sweetness transitions into a more savory-sweet profile, reminiscent of butter biscuits and toasted marzipan. You will notice a distinct development of woodiness, specifically aged cedar, complemented by rich leather and a touch of white pepper on the retrohale. The texture of the smoke becomes oilier and more luxurious, with secondary notes of pecan and baking spices like nutmeg and cinnamon adding layers of intrigue to every puff.
Final Third – The Crescendo
In the final act, the H. Upmann Sir Winston reaches its peak intensity. The strength remains firmly in the medium category, but the body swells to a medium-full presence. The earlier creaminess is replaced by a more robust cocoa and dark chocolate character. A lively uptick in strength brings forward notes of roasted coffee beans and deep earth, yet it never loses its fundamental balance. There is no bitterness here; instead, the sweet, creamy character of the first half lingers in the background, providing a harmonious counterpoint to the more potent finish. It is a slow, dignified burn that invites you to smoke it until your fingers can no longer hold the nub.
Finish
The finish is perhaps the most rewarding aspect of this premium Cuban cigar. It is exceptionally clean, mellow, and luxuriously smooth. The aftertaste lingers with a subtle sophistication, leaving a memory of sweet wood and toasted nuts on the palate long after the cigar has been extinguished. It is the kind of finish that demands a moment of silence to fully appreciate the craftsmanship involved.
Flavor Wheel
| Primary Notes | Creamy Chocolate, Floral Sweetness, Toasted Cedar |
| Secondary Notes | Butter Biscuits, Marzipan, Roasted Pecan |
| Tertiary Notes | Leather, White Pepper, Baking Spices (Nutmeg) |
| Finish | Clean, Mellow, Lingering Cocoa and Wood |
| Aroma | Rich Earth, Citrus, and Toasted Tobacco |
Aging and Collector Value
The H. Upmann Sir Winston is legendary among collectors for its extraordinary aging potential. While many cigars reach their peak at the three-year mark, the Sir Winston is known to evolve beautifully over decades. In its youth (1–3 years), the cigar is vibrant and floral, with a lively spice. However, with 5 to 10 years of proper humidification, the flavors meld into a seamless tapestry of cream, honey, and soft leather. The tobacco from the Vuelta Abajo region is particularly high in essential oils, which allows the cigar to gain body and “chewiness” over time without becoming harsh.
For the serious collector, the Sir Winston is a staple. Its production is often lower than other Churchills like the Romeo y Julieta Churchill, making it a rarer find on the market. To preserve its grand reserve potential, we recommend storing these cigars at a consistent 65-72% humidity and a temperature of 65-70°F. Using a cedar-lined humidor is essential, as the wood interacts with the H. Upmann blend to enhance those signature biscuit and cedar notes. Whether you are looking for a celebratory smoke for a milestone or a long-term investment for your humidor, the Sir Winston is a blue-chip choice.
Perfect Pairings
| Beverage | Why It Works |
|---|---|
| Vintage Champagne | The effervescence and acidity of a fine Krug or Dom Pérignon cut through the cigar’s creaminess, highlighting the floral and citrus notes. |
| Aged Cognac (XO) | The dried fruit and oak notes of a premium Cognac mirror the woodiness and leather of the Sir Winston, creating a decadent, classic pairing. |
| Single Malt Scotch | A Speyside malt with sherry cask influence provides a fruity sweetness that complements the baking spices and marzipan of the middle third. |
| Aged Cuban Rum | The natural molasses and vanilla sweetness of an 11-year-old Cuban rum amplify the chocolate and biscuit profile of the cigar. |
| Double Espresso | For a daytime smoke, the intense bitterness of a short black coffee provides a beautiful contrast to the Sir Winston’s inherent sweetness. |
Authenticity Verification
In the world of authentic Habanos, peace of mind is as important as the smoke itself. We ensure that every box of H. Upmann Sir Winston we provide meets the rigorous standards of Cuban craftsmanship and legal exportation.
- Habanos Holographic Seal – Every box features the official Habanos holographic seal on the top right corner, which includes a unique barcode and hidden security features visible under UV light.
- Box Code Verification – The bottom of each box is hot-stamped with the factory code and the date of production (e.g., UBM MAY 23), allowing you to track the exact origin and age of your cigars.
- Factory Stamp – Look for the “Totalmente a Mano – Tripa Larga” stamp, confirming the cigar was made entirely by hand using long-filler tobacco.
- Triple Cap – The Sir Winston features a traditional Cuban triple cap, a mark of expert rolling that ensures a clean cut and a perfect draw.
Our Guarantee: If any cigar fails Habanos verification, we provide a full refund. Trusted by collectors since 2015, we take pride in delivering only the finest Vuelta Abajo tobacco products to our global clientele.
Frequently Asked Questions
What is the flavor profile of H. Upmann Sir Winston?
The H. Upmann Sir Winston is celebrated for its medium-bodied elegance. It begins with notes of floral sweetness and creamy chocolate, evolving into a complex heart of toasted wood, butter biscuits, and light pepper. The finish is famously smooth, with a lingering sweetness and a rich, earthy aroma that defines the H. Upmann brand.
How long does H. Upmann Sir Winston take to smoke?
Due to its Julieta No. 2 (Churchill) vitola, which measures 178 mm (7 inches) with a 47 ring gauge, this cigar is designed for a leisurely experience. Most smokers will find it takes between 75 and 90 minutes to fully enjoy the evolution of the blend. It is a cigar meant for reflection and relaxation, not a rushed break.
Is H. Upmann Sir Winston a good cigar for aging?
Absolutely. It is widely considered one of the best Cuban cigars for long-term aging. While it is enjoyable upon release, the Sir Winston truly transforms after 5 years in a humidor. The flavors become more integrated, the creaminess intensifies, and any youthful edges of pepper soften into a sophisticated, nuanced masterpiece.
What vitola is H. Upmann Sir Winston?
The factory name for the Sir Winston is Julieta No. 2. In the commercial market, this is universally recognized as the Churchill size. This format is prized by experienced smokers because the length allows the smoke to cool as it travels through the cigar, while the 47 ring gauge provides the perfect ratio of wrapper to filler for maximum flavor delivery.
