H. Upmann Sir Winston vs Montecristo No. 2
How do H. Upmann Sir Winston and Montecristo No. 2stack up? Here's the head-to-head — strength, wrapper, flavor, size, and critic ratings — plus which one to reach for.
The short answer
The Montecristo No. 2 is the fuller, stronger smoke (Medium-Full); the H. Upmann Sir Winston is the milder of the two (Medium).
- Strength
- Body
- Medium
- Medium-Full
- Origin
- Cuba
- Cuba
- Wrapper
- Cuban
- Cuban
- Binder
- Cuban
- Cuban
- Filler
- Cuban
- Cuban
- Vitola
- Churchill
- Torpedo (Pirámide)
- Size
- 7 in × 47
- 6.1 in × 52
- Rating
- 94/100 · 2018
- 96/100 · 2013
- Flavor
- ChocolateMarzipanFloralGraham crackerCedar
- CocoaCoffeeCedarEarthBlack pepper
The verdict
- Strength
- Montecristo No. 2 is the bolder smoke (Medium-Full vs Medium). New to cigars? H. Upmann Sir Winston is the friendlier place to start.
- Critic scores
- Montecristo No. 2 edges it on published critic scores (94 vs 96).
Both are worth knowing — the "better" cigar is the one that fits your taste and the moment.
Choose H. Upmann Sir Winston if
you want the milder, more beginner-friendly smoke, or sweet notes appeal to you.
See H. Upmann Sir Winston →Choose Montecristo No. 2 if
you want a bolder, fuller-bodied cigar, or sweet notes appeal to you.
See Montecristo No. 2 →H. Upmann Sir Winston vs Montecristo No. 2 — FAQ
- Is the H. Upmann Sir Winston or the Montecristo No. 2 better for beginners?
- The H. Upmann Sir Winston is the gentler of the two (Medium-bodied), which usually makes it the friendlier pick for a newer smoker.
- Is the H. Upmann Sir Winston or the Montecristo No. 2 stronger?
- The Montecristo No. 2 is stronger — it's Medium-Full-bodied, versus Medium for the H. Upmann Sir Winston.
- What's the difference between the H. Upmann Sir Winston and the Montecristo No. 2?
- The H. Upmann Sir Winston is a medium Cuban cigar with a Cuban wrapper; the Montecristo No. 2 is a medium-full Cuban cigar with a Cuban wrapper.
- Which is rated higher, the H. Upmann Sir Winston or the Montecristo No. 2?
- H. Upmann Sir Winston: Cigar Aficionado 94/100. Montecristo No. 2: Cigar Aficionado 96/100.