1970s H. Upmann Sir Winston

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Been waiting patiently to try this since getting a few of these earlier this year. Lots of positive comments have been made of older H. Upmann Sir Winstons. They have been beautifully maintained and was excited to finally have the time to smoke this cigar.

Let’s see how this is progressing….

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The 1970s H Upmann Sir Winnie is a beautiful looking cigar. It has aged gracefully, like a fine wine. It comes in at a 47 ring guage and is 7 inches in length. It is a Julieta No. 2 vitola. I love how ornate band on this cigar. So elegant and classy looking.

I’ve been told that the Sir Winstons are only made when the best tobacco is available. There are some years where they are not produced.

The wrapper is a beautiful shade of golden, leathered brown. Pristine despite its age. No apparent veins to speak of. Perfect. Very box pressed which is interesting, considering it was sleeping in a varnished cedar box. Aromas of graham cracker and honey emanate from the wrapper. Not very faint. Can’t wait to fire this up.

The construction is impeccable. Nice and firm throughout the cigar with the slight give when squeezed. The triple cap is perfectly applied and the foot is nicely packed.

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A quick twist of my punch and we are ready to go.

The draw is perfect. Nice airflow with a slight resistance.

Initial flavours are honey, cocoa and graham cracker.

Time to take this to the flame….

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First Third
Very clean and smooth. Subtle. Strength is mild to medium. Clean tobacco taste with touches of nutmeg, star anise, bitter cocoa and graham cracker.

The burn is impeccable. Razor sharp. Nice and even with every draw. Draw and smoke production is excellent. The ash is a ‘Dirty’ white with a touch of grey.

The retrohale comes as clean tobacco. There is a purity to this. Hints of honey and spice gently makes its way through the nasal passages.

The after finish is a little short. Not hard hitting at all. Very relaxed and gentle on the palate. Bitter chocolate, honey and a touch of star anise. A little hint of sour dough bread at the back end. Very interesting flavour profile. Lasts on the palate despite the strength is at a mild to medium level. Need to pay attention as the nuances are slight and discreet.

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Second Third
Tangy now. More depth to the cigar. Floral notes and a touch of citrus join cocoa, graham cracker and honey. The star anise note is fading. Strength has picked up slightly, barely making the medium level.

The retrohale is has hints of nutmeg, cocoa, honey and floral notes. More character to it now.

The after finish is very luxurious. Subtle, discreet and ever changing. Nice level of complexity. The addition of floral and citrus notes really livens up the party, combining nicely with the bitter chocolate, nutmeg and graham cracker. The flavour profile is lasting a bit longer on the palate but still falls short. The star anise and sour dough bread make brief cameo appearances here and there. Lots of subtle changes with each puff. Very unique.

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Final Third
Violets, honey, nutmeg and cocoa start to really profile themselves. Star anise is back. The citrus notes and graham cracker have dissipated slightly. A clean tobacco flavour also becomes more prominent. Strength is back to mild to medium level.

A sourness is starting to work its way through. A combination of star anise and sour dough bread. Takes away from the flavour profile as when it comes into play, it comes out hard and strong. A little racy. The nicotine is starting to build up. Might have to snip the cigar and purge it.

The retrohale is nice. It’s the after finish that is a little fleeting. The retrohale comes in with honey, graham cracker, floral notes and nutmeg.

The after finish improves after a quick cut and purge. Bitter chocolate, honey, and graham cracker come out strongly but give way to star anise and sour dough bread. A polarizing flavour profile. Lots of nuance and distinct changes now. Strength keeps trying to move into the medium category but falls short. Sometimes, a spike leads to a sharp note of star anise and sour dough bread.

Starting to turn for the good. The sour dough and star anise have faded away, leaving honey, graham cracker, bitter chocolate and floral notes. Singing now. The smoothness of the cigar is impressive. Nice way to finish things off.

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Final Impressions
A very unique flavour profile. Lots of different twists and turns. I suspect that the nicotine build up had a big influence and maybe should have addressed it earlier. There is a ‘clean’ tobacco taste that I only get with vintage cigars. I liked the nuance and subtleness of the cigar. Will have to smoke the next one very slowly to see if that has an influence as well.

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4 Responses to 1970s H. Upmann Sir Winston

  1. Deem Rahall says:

    Thanks for another nice review. Love the band. I missed out on these when they were recently available. I don’t feel that bad now.

  2. Tom G says:

    Lovely review and a superb site. But what do you mean by snipping and purging? Im intrigued.

    • Thanks for the compliment.

      What I mean by sipping is taking slow, long puffs, much like sipping on a scotch. Allowing the flavours to envelop your palate to maximize the taste and to enjoy the flavour profile. It also refers to taking time between puffs so that the cigar doesn’t burn to hot and char the flavours.

      In terms of purging, my version is snipping the head of the cigar if there is nicotine build up as well as blowing through the cigar to ‘purge’ it.

      Hope this helps

      Be well

  3. Ryan says:

    I love this blog!!! Great work bud! Thanks so much!

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