10 H. Upmann Sir Winston

cabaiguan juan

Well-Known Member
This was another cigar which i was looking forward too. I has a loose draw by Cuban standards but how I prefer my cigars to be. The construction was good. It had medium strength. It starts off with spice like red pepper, cream and chocolate dust. At times the pepper kicks up and at times the cream kicks up and at times the chocolate picks up. It’s the most complex Cuban I’ve had to date. Those core flavors rotated through the smoking experience through out the duration of the smoke.
Construction: Great
Taste: Red pepper, cream and chocolate
Opinion: This was a great cigar.
Strength: Medium
Would I buy it: Yes, but on a GB as I don't necessarily want to commit the funds necessary to purchase a box from what I think it costs.
Would I smoke again: Absolutely


Love this place...
Depending on the age of Sir Winstons, flavors intensify greatly... A 3 yo SW is just about the youngest you want to smoke (it’s a waste to smoke them younger, just like drinking an exceptional wine before it’s time) 3 to 5 years, delicately sweet wood, hay, leather and a bit of spice on the retro, and slightly creamy, medium body... 6 to 12 years, sweet wood, a bit of nutmeg, bittersweet chocolate and distinctly creamy, medium full... 15 to 20 years, sweet exotic woods, the finest Corinthian leather, loads of nutmeg and milk chocolate, and a perfect amount of white pepper on the retro...full flavored. You can probably tell that I’m a big fan of these.


Well-Known Member
Nice review. I’ve been gifted a few and bought a few, great smokes! I can’t seem to pull the trigger on a box knowing I’d have to sit it for several years or 15 to 20 years in Bill standards 🤣 ! Truly love the knowledge sharing here!


Well-Known Member
I have had the greatest respect for Sir Winston. Back when trying to find his stick was the RjY. Now we have H Upmann and Davidoff trying to steal the thunder. So does anyone actually "know" what his stick was? Then a CigSid question, are any on those original boxes still around if you have the coin to pry them loose.