Cigar Aficionado

H. Upmann Sir Winston
Sir Winston
47 47
Tasting Note
Rich and refined, this cigar elegantly layers notes of nutmeg and clove with sweet spices and graham cracker. All come together for a delicious Christmas-cake effect.
Body Medium
Size Churchill
Ring Gauge 47
Length 7"
Filler Cuba
Binder Cuba
Wrapper Cuba
Issue Cigar Aficionado – Feb 01, 2017
Price £30.15
Box DateOct. 2013
More Reviews of this Cigar
Issue: Cigar Aficionado: Jan 01, 2019 | Score: 94

One of the last Cuban Churchills in the Habanos S.A. portfolio is the H. Upmann Sir Winston. It doesn't seem right that such a classic format has been deleted from almost every Cuban brand, but the trend is leaning towards fatter, shorter cigars. We at Cigar Aficionado have lamented this tragedy before, but there's no sense in wasting too much time on what's been lost. Rather, let's focus on the Sir Winston. Its dimensions, 7 inches by 47 ring gauge, are nearly perfect. It's thick enough to deliver ample smoke, thin enough to fit comfortably in your mouth and long enough to give you at least an hour of pleasurable smoking. It's medium bodied, making it approachable for beginners but complex enough for more experienced smokers. The cigar is brimming with refined chocolate, marzipan, floral notes and a sweet, graham cracker finish, all brought together by that unique, inimitable Cuban taste. The size is known as a Julieta No. 2 in Cuban cigar factories, and was a favorite of Winston Churchill, perhaps the most famous cigar smoker in history. He consumed so many Julieta No. 2 cigars that the grand and elegant size was eventually named after him. It's only proper that the H. Upmann Sir Winston happens to be a Churchill.

Issue: Cigar Aficionado: Aug 01, 2018 | Score: 94

A sweet and nutty smoke exhibiting the luxurious qualities of fine chocolate, marzipan and gingersnaps, all brought together by a slightly floral, graham cracker finish. Complex and delicious.

Issue: Cigar Aficionado: Apr 01, 2015 | Score: 92

There's a rich, malty quality to this creamy smoke, which also imparts sweet touches of peanuts and honey before a slightly peppery finish. The draw is a bit firm.

Issue: Cigar Aficionado: Feb 01, 2014 | Score: 89

White pepper and toast are the predominant notes found in this Churchill. Touches of grass also come through before a finish smacking of coffee bean.

Issue: Cigar Insider: Aug 27, 2013 | Score: 89

White pepper and toast are the predominant notes found in this Churchill. Touches of grass also come through before a finish smacking of coffee bean.

Issue: Cigar Aficionado: Apr 01, 2013 | Score: 91

Medium-bodied in strength, this cigar is complex and harmonious with clear impressions of ground coffee and graham cracker. There's also an unmistakable dried orange peel flavor.

Issue: Cigar Aficionado: Jun 01, 2012 | Score: 94

A well made cigar whose flavors and complexity build with each puff. Light cedar and nutty notes become more profound almond and marzipan before coffee, leather and floral intonations.

Issue: Cigar Aficionado: Aug 01, 2011 | Score: 93

Lightly hued and medium-bodied, this Churchill is full of flavor ranging from toast and tea to rich nuts with an underlying sweetness. Balanced and dynamic.

Issue: Cigar Aficionado: Aug 01, 2010 | Score: 92

Ample layers of dense smoke come out of this cigar's every draw. Flavors are loaded with nuts, rich tobacco and cocoa bean. Cinnamon and woody notes linger on the finish.

Issue: Cigar Aficionado: Jun 01, 2008 | Score: 92

Beautiful to behold with a silky, oily wrapper and excellent cap. The first puffs are immediately rich with leather and spice underscored by woody, meaty undertones throughout. It will age well.

Issue: Cigar Aficionado: Apr 01, 2007 | Score: 91

A very attractive Churchill with great oils and a nice cap. The cigar warms nicely to show rich and toasty leather and earth flavors, complemented by cedar notes and a nutty finish. A medium- to full-bodied cigar.

Issue: Cigar Aficionado: Aug 01, 2005 | Score: 90

An attractive reddish-brown cigar with a fine draw. It’s rich, toasty and woody, with hints of nuts, leather and hickory wood. It has a long finish. Medium bodied and elegant.

Issue: Cigar Aficionado: Dec 01, 2004 | Score: 88

This cigar burns and draws well. It’s smooth, toasty and cedary, with a hint of coconut. The finish is spicy.

Issue: Cigar Aficionado: Aug 01, 2003 | Score: 89

Well made, with a fine cap. It's rich and meaty, with coffee flavors and a dry element to the finish. Medium to full in body.

Issue: Cigar Aficionado: Dec 01, 2002 | Score: 90

A well-made double corona with good oils. It's rich, woody and toasty, with coffee flavors. Medium to full bodied.

Issue: Cigar Aficionado: Apr 01, 2002 | Score: 89

A bit pale, but otherwise well made, this cigar has an almond flavor, along with hints of creamy sweet coffee. Medium to full bodied.

Issue: Cigar Aficionado: Apr 01, 2001 | Score: 87

A big, well-made cigar with a well-finished cap. It has a firm draw and a thick gray ash. It's meaty and leathery, with woody, syrupy notes. A full bodied cigar.

Issue: Cigar Insider: Nov 01, 2000 | Score: 87

A beautiful, oily cigar with a perfect cap. Some tasters noted a tight draw. The smoke is floral and sweet, but sometimes showed sour flavors on the finish. This cigar shows real inconsistency, perhaps due to youth. Box age should provide better results.

Issue: Cigar Insider: Jun 01, 1999 | Score: 90

There are some construction flaws on this big cigar, but it burns evenly with a slightly tight draw. It's light and creamy, with hints of ginger and cinnamon. It lacks complexity.

Issue: Cigar Insider: May 01, 1997 | Score: 89

An oily wrapper that is spotty and veiny. The tip is a bit soft, but this cigar is loaded with rich, complex flavors, including cedar, leather and fruit. Not quite as powerful as it appears.

Issue: Cigar Insider: Mar 01, 1996 | Score: 91

This big cigar is extremely well-made. It burns well with a gray ash, delivering heavy wood flavors with spice. A well-balanced cigar that will improve with age.

Issue: Cigar Aficionado: Jan 01, 1970 | Score: 93

Large cigars have gone almost completely out of fashion. It’s not that their quality has diminished: they still deliver loads of flavor with a cool, refined character. The problem is that few people have the time to smoke such a large cigar as the Sir Winston—let alone such longer ones as double coronas. But aficionados who do opt for a large cigar usually puff on a Romeo y Julieta Churchill or a Cohiba Esplendido. Perhaps that’s why Cuba makes so few Sir Winstons, most of which are rolled in the new H. Upmann factory on the outskirts of Havana. Until the mid-1990s, the cigar came in a smart green lacquered box, but today it comes in a varnished cedar one with a clasp. The band, once the standard brown and white H. Upmann, is now gold, white and red. Find some time if you are going to smoke this. It’s worth relaxing and contemplating what the Sir Winston has to offer. It’s so good to look at that you may not want to see it go up in smoke. The ones we smoked had beautiful silky, oily wrappers and excellent caps. The first puffs were immediately rich with leather and spice, then developed into woody, meaty undertones. This cigar has the richness and structure to age well. We think that Winston Churchill would have loved this cigar.

Cigar Aficionado's 100-Point Scale
  • Classic: 95-100
  • Outstanding: 90-94
  • Very good to excellent: 80-89
  • Average to good commercial quality: 70-79
  • Don't waste your money: 0-69
100-Point Scale