What is the size and ring gauge of H. Upmann Sir Winston cigars?

The H. Upmann Sir Winston measures 7 inches (178mm) in length with a 47 ring gauge, classifying it as a Julieta No. 2 vitola. This substantial format provides approximately 90-120 minutes of smoking time. The cigar's generous dimensions allow for a gradual development of its characteristic medium-bodied profile, with the larger ring gauge contributing to a cooler, more measured burn throughout the experience.

What does H. Upmann Sir Winston taste like and how does the flavor evolve?

The Sir Winston delivers a refined medium-bodied experience beginning with cedar and toasted bread notes. The first third introduces subtle citrus and floral undertones characteristic of H. Upmann's lighter house style. By the midpoint, cocoa and roasted coffee emerge, building into a final third of leather, nutmeg, and gentle spice. The cigar maintains remarkable balance throughout, never overwhelming the palate despite its length, with a consistent creamy texture from start to finish.

How does H. Upmann Sir Winston compare to Cohiba Esplendidos and is it worth the price?

Both share the Julieta No. 2 vitola, yet diverge significantly in character. The Sir Winston offers a more restrained, elegant profile versus the Esplendidos' fuller, more assertive delivery. Sir Winston typically commands a lower price point while providing comparable construction quality and aging potential. For enthusiasts seeking a sophisticated, medium-bodied Cuban with historical significance and consistent availability, it represents sound value—particularly for those who find Cohiba's pricing prohibitive or prefer subtler complexity.

Cigar Information

H. Upmann Sir Winston

Isabella MoránSenior Writer

The H. Upmann Sir Winston stands as one of the most distinguished cigars in the brand's regular production lineup. Named in honor of Britain's legendary Prime Minister, this elegant cigar has been a fixture in the H. Upmann portfolio since its release prior to 1960, demonstrating remarkable staying power in an ever-evolving market.

Specifications

Cigar Name	Sir Winston
Factory Name	Julieta No.2
Ring Gauge	47
Length	178 mm (7 inches)
Official Weight	15.07 g
Construction	Handmade
Status	Current Regular Production

Band History

The Sir Winston's presentation has evolved considerably over the decades. During the 1970s, these cigars featured a distinctive variation of band B, characterized by a gold border accompanied by the inscription "Finest Selected Tobacco." By the late 1970s, the brand transitioned through standard bands A, B, and finally C, which remains in use today.

Packaging

Collectors and enthusiasts will find the Sir Winston housed in high-quality boîte nature boxes containing 25 cigars. The current presentation features a varnished finish, a style introduced around 1994. Prior to this, the cigars were offered in green painted boxes of equal quality, which were discontinued at approximately the same time the varnished version debuted.

Historical catalogues from the late 1970s occasionally depict Sir Winston cigars presented in dark brown varnished boxes or black painted packaging, reflecting the evolving aesthetic preferences of different eras.

Flavor Profile and Tasting Notes

The Sir Winston delivers a sophisticated smoking experience characterized by remarkable elegance and balance. Based on 57 enthusiast reviews, this cigar earns consistently strong ratings across all measured categories.

Elegance	4/5
Balance	4/5
Strength	3/5
Complexity	4/5
Aftertaste	4/5
Overall Rating	4.28/5

The flavor profile showcases a beautiful interplay of notes, with shortbread emerging as the most frequently detected characteristic. The cigar offers a medium-bodied experience with a strength rating of 3 out of 5, making it approachable yet sufficiently complex for seasoned palates.

Primary Tasting Notes:

Shortbread
Coffee
Cream
Nut
Cedar
Leather
Cinnamon
Tobacco

Secondary Notes: Almond, caramel, vanilla, wood, baking spice, earth, hazelnut, milk chocolate, walnut, bitter chocolate, cocoa, pepper, and white pepper also make appearances throughout the smoking experience.

Subtle Undertones: Attentive smokers may detect traces of anise, butter, citrus, cookie, graham cracker, grass, hay, salt, sourdough, spice, and spiced cake.

Related Releases

The Sir Winston name has also graced special limited editions, including:

H. Upmann Sir Winston Siglo XXI Millennium Humidor
H. Upmann Sir Winston Gran Reserva Cosecha 2011

These special releases celebrate the enduring legacy of this iconic vitola while offering collectors unique expressions of the classic blend.

Questions & Answers