Is the H. Upmann Sir Winston a good cigar for beginners?

It's a good next step. Medium-bodied cigars are fine once you've enjoyed a few milder ones and want more flavor and depth.

How strong is the H. Upmann Sir Winston?

The H. Upmann Sir Winston is Medium-bodied. Strength is about body and nicotine rather than flavor, so eat something first and take it slow if you're sensitive.

What does the H. Upmann Sir Winston taste like?

Expect chocolate, marzipan, and floral, leaning sweet. Tasting notes are a guide — your palate may pick up more or less.

What is the H. Upmann Sir Winston's rating?

Published critic scores: Cigar Aficionado 94/100 (2018). Casa DNC aggregates third-party ratings and doesn't score cigars itself.

What pairs well with the H. Upmann Sir Winston?

It pairs well with aged rum and cognac. As a rule, match the drink's intensity to the cigar's medium body.

How long does it take to smoke the H. Upmann Sir Winston?

Plan on about 75 minutes for the churchill — longer if you smoke slowly, which keeps it cool and tasting its best.

H. Upmann

CubanAficionados

H. Upmann Sir Winston

H. Upmann's flagship Cuban churchill, named for Winston Churchill — refined chocolate, marzipan and floral notes over a 90-minute smoke.

Strength

MediumSmoke time ~75 min

The short answer

The H. Upmann Sir Winston is a balanced, medium-bodied smoke — a Cuban churchill with a Cuban wrapper. Expect chocolate, marzipan, and floral. Critics rate it 94/100.

Flavor profile

Sweet · Balanced · Herbal · Earthy

ChocolateMarzipanFloralGraham crackerCedar

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 verdict

The H. Upmann Sir Winston is a balanced, medium-bodied smoke from H. Upmann. It's a Cuban churchill wrapped in Cuban at 7 in × 47.

On the palate, expect chocolate, marzipan, and floral, leaning sweet. Plan on roughly 75 minutes from light to nub.

It's well regarded: Cigar Aficionado rated it 94/100 in 2018. It pairs naturally with aged rum and cognac. If you're newer to cigars, this is a safe, enjoyable pick.

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.