About the H. Upmann Sir Winston
Few Havana houses carry the quiet authority of H. Upmann, founded in the Cuban capital in 1844 by Herman Upmann, a German banker whose love of fine tobacco outlived his bank. The brand built its reputation on light to medium-bodied Habanos rolled entirely by hand with long filler from the Vuelta Abajo region of Pinar del Rio. The Sir Winston, named in tribute to Winston Churchill, sits at the pinnacle of that lineage and remains one of the few true Cuban Churchills still produced. Known inside the factory as the Julieta No. 2, it measures a stately 7.0 inches with a 47 ring gauge, a format meant to be savored rather than rushed.
Flavor profile by thirds
The opening third leans elegant and approachable, with sweet, floral top notes giving way to soft cedar and a touch of cinnamon. Through the middle the cigar gathers weight, layering refined chocolate, marzipan, and nougat over a creamy, biscuity core that keeps the smoke remarkably smooth. As it reaches the final third the body edges toward the fuller side of medium, drawing out hints of leather, roasted nut, and a lingering graham cracker sweetness that defines the close.
Pairings
- An aged Cuban or Dominican rum, whose caramel and oak notes echo the cigar’s nutty sweetness.
- A lightly peated single malt Scotch that frames the chocolate and leather without overwhelming the floral character.
- A strong black espresso or Cuban coffee to mirror the creamy, biscuit-like center.
Aging and storage
The Sir Winston is a natural candidate for the cellar, and many enthusiasts find its floral edges mellow into deeper chocolate and dried-fruit tones after a few years of rest. Keep it in a well-seasoned humidor held around 65 to 70 percent relative humidity and a steady temperature near 65 to 68 degrees Fahrenheit. At a 47 ring gauge it benefits from patient storage, so give freshly arrived boxes a few weeks to settle before lighting your first stick.
Who it is for
This is a cigar for the unhurried smoker who values balance and refinement over sheer power. Newcomers will appreciate its forgiving, mild to medium strength, while seasoned aficionados return for the layered complexity that unfolds across a smoke of an hour or more. If you enjoy a classic Churchill with a famous name and authentic Havana heritage, the Sir Winston earns its place in the rotation.
Frequently asked questions
How strong is the H. Upmann Sir Winston?
It is generally mild to medium in body, opening gently and building toward the fuller side of medium in the final third, which makes it accessible yet rewarding.
What size is the Sir Winston?
It is a Churchill, known in the factory as the Julieta No. 2, measuring 7.0 inches in length with a 47 ring gauge.
How long does it take to smoke?
Given its generous Churchill format, expect a relaxed smoke of roughly an hour to ninety minutes when enjoyed at an easy pace.
Explore more
Browse all H. Upmann cigars, see our H. Upmann price guide, or try the H. Upmann Magnum 56 EDICION LIMITADA 2015 and H Upmann No.2. Store yours in a seasoned humidor and see our guide on how long cigars last. Learn more from its Cigar Aficionado rating, Wikipedia, the official Habanos S.A. site.
