H. Upmann
CubanAficionadosH. Upmann Sir Winston
H. Upmann's flagship Cuban churchill, named for Winston Churchill — refined chocolate, marzipan and floral notes over a 90-minute smoke.
Critic ratings
Cigar Aficionado
2018
94/100
Scores as published by each reviewer. Casa DNC aggregates third-party ratings; we don't score cigars ourselves.
The Sir Winston is the crown jewel of the Cuban H. Upmann range, named after Winston Churchill, who favored the brand. Built on the Julieta No. 2 (churchill) format at 7 inches by a 47 ring gauge, it's a long, stately smoke of about 90 minutes, rolled entirely from Vuelta Abajo tobacco.
What it tastes like
This is H. Upmann at its most refined: chocolate and marzipan, delicate floral notes, and a sweet graham-cracker finish, all carried by that unmistakable Cuban character. It's a medium-bodied cigar that prizes elegance and complexity over power, evolving gracefully across its long burn. The slim-for-its-length ring gauge sits comfortably in the mouth while still delivering ample smoke.
Who it's for
A special-occasion cigar for aficionados who can give it the full hour and a half it deserves. It's a benchmark Cuban churchill and a frequent Cigar Aficionado favorite. Pair it with an aged rum or a cognac.
If 90 minutes is too long, the Connoisseur No.1 robusto offers a shorter dose of the house style. For background on how Cuban tobacco differs from the rest, see Cuban vs Nicaraguan cigars. Track this milestone smoke in the Casa DNC app.
Curious how it stacks up? See Cuban vs Nicaraguan cigars.
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H. Upmann Sir Winston head-to-head
See how H. Upmann Sir Winston stacks up against similar cigars — strength, flavor, and ratings.