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Rates the H. Upmann Sir Winston


TopCubans Past experience:

Richards Favorite: In all its grand splendour this noble cigar never ceases to adorn the palate with exacting aromas of musk, wood and toasty coffee flavours. Exeptional quality, first class presentation this is a big smoke, for a big smoker. Deep, rich foods and heavy, heady wines and liquors, form a divine symbiosis with this most 'Sir Winston' of Churhills. A must try for anyone who is passionate about cigars!

TopCubans member's experiences:


On 2013-03-11

" i smoke only cubans and i have tried many, but this stays my preferred cigar by far.
complex, well balanced, constant, the perfect cigar for me "

Alex Bryant

On 2012-08-03

" Wow, I would smoke this cigar everyday. But that would be a waste. This is a important cigar for an important moment. Have this with good friends and a good wine because this cigar will make you want it again and again. This, and the Esplendidos are the 2 cigars that make me feel like I'm doing everything right, and that these cigars make it even better. Keep these on hand for when your team wins their league, or when you get promoted, because these are for great moments. "


On 2009-05-21

" In our regular cigar nights a month ago, we opened a box from 2001. I was blown away but the flavors and for me this is the best cigar I have ever smoked. Needless to say, I bought two boxes immediately. "


On 2009-01-07

" Impeccable. Gorgeous to behold, draws like a dream, nice even burn, and a level of aroma complexity you'd expect from from a '82, '86, or '89 Bordeaux. This is one I'd LOVE to fill the humi with. But at this price point and with this economy, I'll have to be content with buying a few here and there. They taste so good that none will ever see plume, not a chance. Cohiba Esplendido? Fuhgeddaboudit! "


On 2008-06-24

" This is a follow-up review. The first one just didn't do it justice. Of the cigars I've tried this one is worthy of a higher than superior rating, therefore a 5+. I told my wife this one is so good I would eat it if I could. The H. Upmann Sir Winston is so good I'm intent on smoking more of my robustos and petit coronas to make room for a full box of these in my humidor. The last one I smoked was so pleasantly rich and smooth with a variety of subtle notes of Italian espresso, spruce, musk, and had a creamy silky smoke. I can't wait to see how these age, if I can keep from smoking them them long enough. Richard, thank you very much for introducing me to these sublime cigars. The price goes against my frugal cigar purchasing attitube, but these are worth it. "


On 2008-06-16

" Richard suggested these when I was looking for a 'perfumey' aroma and my wife got a few for me for Father's Day. I know I'm supposed to let them rest for a few days in the humidor, but with my favorite chili lime shrimp, followed by a 20 year old Pappy Van Winkle bourbon, I couldn't wait. I knew the Sir Winston was something special with that first puff. I had an hour plus of pleasure. The smoke was silky, had nuances of espresso and seasoned wood with a rich flavor and hint of perfume. This will be certainly be my next full box purchase. They are beautifully constructed and just a pleasure to hold. I considered myself a robusto or petitit corona smoker, but Richard now has a convert. "


On 2007-11-20

" Have a box purchased in Madrid dated June, 2002. Amazing smokes that get better w/ time! "

The Mollianus

On 2005-07-16

" Great name, great cigar. Excellent draw and taste. Really a stayer in my Humidor! "


On 2005-05-09

" wow!!!!Richard has struck again.This has to be the flag ship of churchill cigars.I smoke this after a good meal&with a dark beer.I could not put this cigar down,i smoked it to a nub.I let it age in my humidor,until it was plumb.This is the best of the spring samples.This is another that will always be in my humidor.The scent of coffee,the great draw,even burn,shell i continue.Thanks Richard! "


On 2005-03-20

" Construction, complex, and rounded. Age only makes it better. Buy 2 boxes, one for now and the other for later. "


On 2004-06-09

" Excellent churchill. In my humble, better than Cohiba or R&J. "


On 2003-11-19

" This was the best cigar I ever had. I splurged and went for the big bucks, but well worth the money. "


On 2003-09-24

" Just one of the best smokes I ever had! Does it get better than this?? "


On 2002-04-28

" given time....cubas finest....enough said. "

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