Sir Winston
H. Upmann / Sir Winston
Length: 7" | Ring Gauge: 47
Strength: Light to Medium | Vitola: Julieta No. 2
£42.70 7% since 1st April 2022

Ratings & Reviews

1 Review
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Review of a 1970's H Upmann Sir Winston that I smoked in August 2013. A friend and I found and split a Mid 1970's "Green box" of Sir Winstons.

Prelight notes:

* Lovely box pressed wrapper
* Light milk chocolate in color
* Light cocoa aroma on the foot
* It doesn't have that "aged" aroma I'm used to. If anything, it smells quite fresh
* The stick passes the pinch test easily. This cigar has been well maintained over the years.
* Cold draw is smooth. Just enough resistance to keep it from being a wind tunnel.

**Please note: Whenever you see a "//" that is a visual cue that another draw has been taken or I've jotted down a thought at the time.

First third

Opening draw // Light toasty tobacco // Nice tangy notes on the finish with slight chocolate // More chocolate notes // Very smooth // Baking spice // Great burn // Dry walnut // Lovely white smoke //

Some sweet notes // Nutmeg on the finish // Very clean tasting // Nutty // A sip to clear the palate // Cashew notes // Hardly get that // A bit faint though // Tangy tobacco // Nutty notes on the finish // More tang // Body is light, flavors aren't // This cigar has something to offer even after all these years // More sweetness // Cocoa powder //

Tangy again // Flaky light gray ash // Very sweet undertones to the cigar but subtle // Very easy smoke // Ash twists and falls off into the ashtray // More smoke now // A hint of strength appears towards the end of the first third // It lasts a few puffs and results in a white pepper finish. More in taste versus potency//

Second third

A few sweet draws start things off // Burn line is great // Some flavourful toasty tobacco now // White pepper more prevalent // Earthy flavors // Very good evolution of flavour thus far // The finish is a nit tangy now // Nuttiness throughout in the background //

Mild medium // No tobacco buzz at all // Ore sweetness // Ash drops unexpectedly // It misses me // A bit more strong notes ensue // Cocoa returns // The draw is perfect so far // More White pepper // Now with some oomph // Interesting how the stronger aspect of a cigar gets locked in deeper towards the head //

Nuts and tangy tobacco // Nice earthy draws follow // Very little smoke production on the cigar // Nutmeg on the finish now // The next draws are tangy with // Hint of minerals // I take a drink to clear the palate // The sweetness i get is akin to light honey flavours // It sticks with me throughout // Another white pepper draw fives way to a mineraly finish //

Final third

A bit more strength in flavour in the past four draws // Earthy and tangy // White pepper returns // Wow // Bean // I get that s lot from Cohiba // Ash fell again // So brittle and powdery //

Sweet and tangy notes // I’m reminded of a Trinidad Fundadores when i get that // The inner portion of the band is nicely yellowed // More beans // Not a boring cigar at all // So smooth // Nutmeg // Toasty tobacco // Throughout this journey // The cigar has burned at a low temp // More beans and white pepper // A bit more smoke now // I got a slight caramel note on the finish // I remove the band // It snaps off easily and intact //

Nuttiness returns // Minerals and bean on the finish // Tangy tobacco // Toasty again // Feeling a slight nicotine buildup as i get halfway through the final third // More beany finishes the last two draws // Slight hints of anise with a sweet finish // Tangy and beany to follow // A few draws of toasty tobacco with a very dry finish // Mineraly again // Pepper finish // Very tart draw // Odd thinking.gif// Back to toasty tobacco // Beany once more //

All cocoa and chocolate notes are long gone by now // Earthy again // So smooth // Nutmeg follows // Going to nub this // Very clean tobacco taste on the next two draws // No harshness to this cigar at all // He next few draws are light in flavour // Faint baking spice at best // Tangy tobacco // Toast // Light citrus note like an orange peel // Again!

Even as i nub this its not very hot // It hasn't needed a relight either // Tangy tobacco // Anise surprises me again at this point // Lovely // My final draw is toasty tobacco with a sweet finish // It's done //


Where to start? This cigar was amongst the best I've ever smoked. It was full of flavour and revealed some stealthy, tobacco strength progressively. The only modern day cigar that does that, IMO is the La Escepcion Selectos Finos RE. This not as powerful as that cigar but it made up in complexity. From the first to the last third this was a journey in taste. It won't "wow" you with very strong notes but it will draw you in slowly with delicate nuances throughout. The best cigar I've smoked thus far is the Cuban Davidoff No 1 (a 1970 vintage). It too was an interesting smoke. It's best quality was it's ability to deliver some really rich flavours past the second half. The Sir Winston was more subtle but doesn't lose marks for "strength". Like any aged cigar, you want to "sip" it. Take it slow and let it do the work. If you're paying attention and it's fared well over the ages, it can reward you. Given how well this smoked. From the variety of tastes, an near perfect burn, excellent draw and not needing a relight, I've got to rank this high up on my list of best smokes. It truly is a "Champagne" of cigars.

And with that said, I give it a score of:


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