H. Upmann Sir Winston – Box of 25 Cigars

The H. Upmann Sir Winston is one of the crown jewels of the H. Upmann portfolio, a cigar revered for its classic Churchill vitola, rich Cuban heritage, and exceptionally refined smoking experience. Named after Sir Winston Churchill, one of history’s most iconic cigar smokers, this cigar honors the statesman’s legacy with elegance, sophistication, and enduring appeal.

Habanos S.A. produces this cigar as part of H. Upmann’s standard premium line, and it remains a favorite among seasoned aficionados seeking a medium-bodied, long-format cigar with complexity, subtlety, and balance.

Vitola and Presentation

• Vitola de Galera (Factory Name): Julieta No. 2

• Commercial Name: Sir Winston

• Length: 178 mm (7 inches)

• Ring Gauge: 47

• Format: Churchill

• Packaging: Dress box of 25 cigars (standard production)

• Construction: Totalmente a Mano – Tripa Larga (Long Filler, Hand-Rolled)

The Sir Winston cigar is beautifully presented in a classic Cuban dress box, banded with the traditional gold and red H. Upmann band, reflecting the brand’s rich legacy and gentlemanly charm.

Origin and Tobacco

• Wrapper / Binder / Filler: 100% Cuban tobacco

• Tobacco Source: Vuelta Abajo, Pinar del Río, Cuba

• Factory: Most often produced at the H. Upmann factory (now part of the Habanos S.A. network)

Every Sir Winston is crafted with aged tobaccos from Cuba’s finest growing region, offering a cigar that consistently delivers grace and complexity in a long, slow-burning format.

Flavor Profile and Smoking Experience

The H. Upmann Sir Winston is known for its mild to medium strength and elegant evolution. It builds in flavor throughout the smoke, maintaining balance and subtlety without overpowering the palate.

Tasting Notes:

• First Third: Opens with classic cedar, hay, and light nutmeg, accompanied by creamy texture and mild sweetness.

• Second Third: Delivers richer notes of toasted almonds, herbal tea, and baking spice, while remaining smooth and aromatic.

• Final Third: Finishes with hints of cocoa, leather, and soft pepper, with a warm and refined retrohale.

Expect a silky draw, razor-sharp burn, and a smoking time of approximately 90–120 minutes, depending on pace. The complexity deepens as the cigar progresses, offering a journey through subtle flavor transitions that reward patience and attention.

Key Details

• Brand: H. Upmann

• Vitola: Julieta No. 2 (Churchill)

• Length: 178 mm (7 inches)

• Ring Gauge: 47

• Strength: Mild to Medium

• Wrapper/Binder/Filler: Cuban (Vuelta Abajo)

• Packaging: Box of 25 cigars

• Flavor Notes: Cedar, almond, tea, spice, cocoa, leather

• Smoking Time: 90–120 minutes

• Availability: Regular production