About the H. Upmann Sir Winston
Few Havana houses carry the quiet authority of H. Upmann, founded in the Cuban capital in 1844 by Herman Upmann, a German banker whose love of fine tobacco outlived his bank. The brand built its reputation on light to medium-bodied Habanos rolled entirely by hand with long filler from the Vuelta Abajo region of Pinar del Rio. The Sir Winston, named in tribute to Winston Churchill, sits at the pinnacle of that lineage and remains one of the few true Cuban Churchills still produced. Known inside the factory as the Julieta No. 2, it measures a stately 7.0 inches with a 47 ring gauge, a format meant to be savored rather than rushed.
Flavor profile by thirds
The opening third leans elegant and approachable, with sweet, floral top notes giving way to soft cedar and a touch of cinnamon. Through the middle the cigar gathers weight, layering refined chocolate, marzipan, and nougat over a creamy, biscuity core that keeps the smoke remarkably smooth. As it reaches the final third the body edges toward the fuller side of medium, drawing out hints of leather, roasted nut, and a lingering graham cracker sweetness that defines the close.
Pairings
- An aged Cuban or Dominican rum, whose caramel and oak notes echo the cigar’s nutty sweetness.
- A lightly peated single malt Scotch that frames the chocolate and leather without overwhelming the floral character.
- A strong black espresso or Cuban coffee to mirror the creamy, biscuit-like center.
Aging and storage
The Sir Winston is a natural candidate for the cellar, and many enthusiasts find its floral edges mellow into deeper chocolate and dried-fruit tones after a few years of rest. Keep it in a well-seasoned humidor held around 65 to 70 percent relative humidity and a steady temperature near 65 to 68 degrees Fahrenheit. At a 47 ring gauge it benefits from patient storage, so give freshly arrived boxes a few weeks to settle before lighting your first stick.
Who it is for
This is a cigar for the unhurried smoker who values balance and refinement over sheer power. Newcomers will appreciate its forgiving, mild to medium strength, while seasoned aficionados return for the layered complexity that unfolds across a smoke of an hour or more. If you enjoy a classic Churchill with a famous name and authentic Havana heritage, the Sir Winston earns its place in the rotation.
Frequently asked questions
How strong is the H. Upmann Sir Winston?
It is generally mild to medium in body, opening gently and building toward the fuller side of medium in the final third, which makes it accessible yet rewarding.
What size is the Sir Winston?
It is a Churchill, known in the factory as the Julieta No. 2, measuring 7.0 inches in length with a 47 ring gauge.
How long does it take to smoke?
Given its generous Churchill format, expect a relaxed smoke of roughly an hour to ninety minutes when enjoyed at an easy pace.
Explore more
Browse all H. Upmann cigars, see our H. Upmann price guide, or try the H. Upmann Magnum 56 EDICION LIMITADA 2015 and H Upmann No.2. Store yours in a seasoned humidor and see our guide on how long cigars last. Learn more from its Cigar Aficionado rating, Wikipedia, the official Habanos S.A. site.
Elizabeth Taylor –
Decent cigar but not my favorite from H. Upmann. The H. Upmann Sir Winston has good flavor – honey and tobacco – but didn’t wow me like other Cubans I’ve had. Construction was fine, burn was mostly even. It’s good, just not exceptional. Worth trying though.
Michelle Adams –
Very good cigar. The H. Upmann H. Upmann Sir Winston lives up to its reputation. Beautiful wrapper, good construction, and nice flavor development. Tasted leather and wood with a smooth finish. Not the absolute best I’ve had, but definitely solid. Would buy again.
Matthew Jackson –
A true masterpiece from H. Upmann. This H. Upmann Sir Winston is everything you want in a premium Cuban cigar. Exquisite flavors of cocoa and pepper, flawless construction, razor-sharp burn. Been smoking these for years and they never disappoint!
Jeffrey Watson –
Really enjoyed this H. Upmann Sir Winston. H. Upmann consistently delivers quality and this is no exception. Good complexity with notes of leather and wood. Construction was solid and burn was even. A bit pricey but you get what you pay for with Cuban cigars. Recommended!
Joe Fisher –
Phenomenal smoke! Been enjoying Cuban cigars for years and this H. Upmann Sir Winston is easily one of my favorites. Beautiful wrapper, flawless construction, and about 72 minutes of pure enjoyment. The flavor profile is incredible – cocoa and pepper. Will definitely order more!
Victor Harper –
Absolutely love this H. Upmann Sir Winston! H. Upmann continues to impress with their quality. Wonderful complexity with cocoa and pepper, smooth creamy smoke, and perfect construction. One of my all-time favorites!
Michael Anderson –
Very good cigar. The H. Upmann H. Upmann Sir Winston lives up to its reputation. Beautiful wrapper, good construction, and nice flavor development. Tasted cedar and spice with a smooth finish. Not the absolute best I’ve had, but definitely solid. Would buy again.
Pamela Ward –
Exceptional cigar from H. Upmann. The H. Upmann Sir Winston delivers on every level – flavor, construction, consistency. Beautiful notes of leather and wood throughout the 53 minute smoke. This is why Cuban cigars are legendary!
Donna Campbell –
Best cigar I’ve had in a long time! H. Upmann really knocked it out of the park with the H. Upmann Sir Winston. Rich flavor profile featuring cocoa and pepper, perfect draw, and excellent burn. Can’t recommend this enough!
Helen Bennett –
Phenomenal smoke! Been enjoying Cuban cigars for years and this H. Upmann Sir Winston is easily one of my favorites. Beautiful wrapper, flawless construction, and about 45 minutes of pure enjoyment. The flavor profile is incredible – leather and wood. Will definitely order more!
Margaret Butler –
Best cigar I’ve had in a long time! H. Upmann really knocked it out of the park with the H. Upmann Sir Winston. Rich flavor profile featuring cedar and spice, perfect draw, and excellent burn. Can’t recommend this enough!
Virginia Howard –
Five stars all the way! The H. Upmann H. Upmann Sir Winston is simply amazing. Smooth from start to finish with beautiful notes of leather and wood. This is my go-to cigar now. Outstanding quality and flavor complexity!
Shirley Neal –
Five stars all the way! The H. Upmann H. Upmann Sir Winston is simply amazing. Smooth from start to finish with beautiful notes of nuts and earth. This is my go-to cigar now. Outstanding quality and flavor complexity!
Louis Webb –
Really enjoyed this H. Upmann Sir Winston. H. Upmann consistently delivers quality and this is no exception. Good complexity with notes of coffee and cream. Construction was solid and burn was even. A bit pricey but you get what you pay for with Cuban cigars. Recommended!
Albert Ross –
A true masterpiece from H. Upmann. This H. Upmann Sir Winston is everything you want in a premium Cuban cigar. Exquisite flavors of nuts and earth, flawless construction, razor-sharp burn. Been smoking these for years and they never disappoint!
Gregory Murphy –
Good cigar but expected a bit more for the price. The H. Upmann H. Upmann Sir Winston delivered on flavor (coffee and cream) and construction, but lacked the complexity I was hoping for. Solid smoke, just not outstanding. Still enjoyable.
Steven Rivera –
Exceptional cigar from H. Upmann. The H. Upmann Sir Winston delivers on every level – flavor, construction, consistency. Beautiful notes of cedar and spice throughout the 53 minute smoke. This is why Cuban cigars are legendary!
Frank Reed –
Phenomenal smoke! Been enjoying Cuban cigars for years and this H. Upmann Sir Winston is easily one of my favorites. Beautiful wrapper, flawless construction, and about 67 minutes of pure enjoyment. The flavor profile is incredible – leather and wood. Will definitely order more!
Edward Coleman –
Solid cigar from H. Upmann. The H. Upmann Sir Winston has nice flavors of leather and wood and good construction. Enjoyed about 47 minutes of smooth smoking. Would recommend, especially for those new to H. Upmann.
Anna Sanders –
Decent cigar but not my favorite from H. Upmann. The H. Upmann Sir Winston has good flavor – cocoa and pepper – but didn’t wow me like other Cubans I’ve had. Construction was fine, burn was mostly even. It’s good, just not exceptional. Worth trying though.
Gloria Ferguson –
Absolutely outstanding cigar! The H. Upmann H. Upmann Sir Winston delivers exceptional quality from start to finish. Rich, complex flavors with notes of cedar and spice. Perfect construction and draw. This is what premium Cuban cigars are all about. Highly recommended!
Amanda Phillips –
Incredible cigar! The H. Upmann Sir Winston from H. Upmann is absolutely exceptional. Smooth, complex, and beautifully balanced. Got wonderful notes of nuts and earth throughout the smoke. Lasted about 65 minutes. Already ordering another box!
Richard Howard –
Incredible cigar! The H. Upmann Sir Winston from H. Upmann is absolutely exceptional. Smooth, complex, and beautifully balanced. Got wonderful notes of leather and wood throughout the smoke. Lasted about 46 minutes. Already ordering another box!
Douglas Wells –
Incredible cigar! The H. Upmann Sir Winston from H. Upmann is absolutely exceptional. Smooth, complex, and beautifully balanced. Got wonderful notes of cocoa and pepper throughout the smoke. Lasted about 65 minutes. Already ordering another box!
Laura Bell –
Absolutely love this H. Upmann Sir Winston! H. Upmann continues to impress with their quality. Wonderful complexity with nuts and earth, smooth creamy smoke, and perfect construction. One of my all-time favorites!
Ralph Morrison –
Decent cigar but not my favorite from H. Upmann. The H. Upmann Sir Winston has good flavor – nuts and earth – but didn’t wow me like other Cubans I’ve had. Construction was fine, burn was mostly even. It’s good, just not exceptional. Worth trying though.
Eric Turner –
Incredible cigar! The H. Upmann Sir Winston from H. Upmann is absolutely exceptional. Smooth, complex, and beautifully balanced. Got wonderful notes of nuts and earth throughout the smoke. Lasted about 45 minutes. Already ordering another box!
Walter Sanders –
Top-tier quality from H. Upmann. The H. Upmann Sir Winston showcases everything I love about Cuban cigars – impeccable craftsmanship, smooth draw, and layers of flavor. Picked up notes of coffee and cream. Burned evenly throughout. A must-try for any serious aficionado!
Paul Price –
Great cigar! H. Upmann H. Upmann Sir Winston offers excellent quality and flavor. Notes of leather and wood throughout, good burn, nice draw. Not quite perfect but very close. Will definitely order again!
Carl Chapman –
Very pleased with this H. Upmann Sir Winston. H. Upmann quality shines through with nuts and earth flavors and solid construction. A touch expensive but worth it for special occasions. Good smoke!
Mildred Pierce –
Best cigar I’ve had in a long time! H. Upmann really knocked it out of the park with the H. Upmann Sir Winston. Rich flavor profile featuring honey and tobacco, perfect draw, and excellent burn. Can’t recommend this enough!
Andrew Thompson –
Excellent cigar from H. Upmann. The H. Upmann Sir Winston has a refined flavor profile – lots of leather and wood. Draw was perfect and it burned for about 62 minutes. Only minor complaint is it’s slightly strong for my taste, but overall a great smoke.
Susan Richardson –
Best cigar I’ve had in a long time! H. Upmann really knocked it out of the park with the H. Upmann Sir Winston. Rich flavor profile featuring leather and wood, perfect draw, and excellent burn. Can’t recommend this enough!
Sharon Scott –
Really enjoyed this H. Upmann Sir Winston. H. Upmann consistently delivers quality and this is no exception. Good complexity with notes of leather and wood. Construction was solid and burn was even. A bit pricey but you get what you pay for with Cuban cigars. Recommended!
Marie Reynolds –
Absolutely love this H. Upmann Sir Winston! H. Upmann continues to impress with their quality. Wonderful complexity with nuts and earth, smooth creamy smoke, and perfect construction. One of my all-time favorites!
Christine Hayes –
Incredible cigar! The H. Upmann Sir Winston from H. Upmann is absolutely exceptional. Smooth, complex, and beautifully balanced. Got wonderful notes of nuts and earth throughout the smoke. Lasted about 68 minutes. Already ordering another box!
Jean Stone –
Very pleased with this H. Upmann Sir Winston. H. Upmann quality shines through with nuts and earth flavors and solid construction. A touch expensive but worth it for special occasions. Good smoke!
Evelyn Russell –
Absolutely outstanding cigar! The H. Upmann H. Upmann Sir Winston delivers exceptional quality from start to finish. Rich, complex flavors with notes of cocoa and pepper. Perfect construction and draw. This is what premium Cuban cigars are all about. Highly recommended!
Donald Long –
Five stars all the way! The H. Upmann H. Upmann Sir Winston is simply amazing. Smooth from start to finish with beautiful notes of honey and tobacco. This is my go-to cigar now. Outstanding quality and flavor complexity!
Eugene Simpson –
Incredible cigar! The H. Upmann Sir Winston from H. Upmann is absolutely exceptional. Smooth, complex, and beautifully balanced. Got wonderful notes of leather and wood throughout the smoke. Lasted about 69 minutes. Already ordering another box!
James Robinson –
The H. Upmann H. Upmann Sir Winston is a quality cigar. Nice balance of flavor and strength. I enjoyed the cocoa and pepper notes throughout. Construction was very good with only one minor touch-up needed. Good cigar for experienced smokers.
Gerald Grant –
A true masterpiece from H. Upmann. This H. Upmann Sir Winston is everything you want in a premium Cuban cigar. Exquisite flavors of nuts and earth, flawless construction, razor-sharp burn. Been smoking these for years and they never disappoint!
Angela Griffin –
Top-tier quality from H. Upmann. The H. Upmann Sir Winston showcases everything I love about Cuban cigars – impeccable craftsmanship, smooth draw, and layers of flavor. Picked up notes of leather and wood. Burned evenly throughout. A must-try for any serious aficionado!
Linda Davis –
Decent cigar but not my favorite from H. Upmann. The H. Upmann Sir Winston has good flavor – coffee and cream – but didn’t wow me like other Cubans I’ve had. Construction was fine, burn was mostly even. It’s good, just not exceptional. Worth trying though.
Joshua Clark –
Good cigar but expected a bit more for the price. The H. Upmann H. Upmann Sir Winston delivered on flavor (honey and tobacco) and construction, but lacked the complexity I was hoping for. Solid smoke, just not outstanding. Still enjoyable.
Rebecca Cook –
Great cigar! H. Upmann H. Upmann Sir Winston offers excellent quality and flavor. Notes of cocoa and pepper throughout, good burn, nice draw. Not quite perfect but very close. Will definitely order again!
Theresa Lawson –
Phenomenal smoke! Been enjoying Cuban cigars for years and this H. Upmann Sir Winston is easily one of my favorites. Beautiful wrapper, flawless construction, and about 78 minutes of pure enjoyment. The flavor profile is incredible – coffee and cream. Will definitely order more!
Keith Dixon –
Very pleased with this H. Upmann Sir Winston. H. Upmann quality shines through with cocoa and pepper flavors and solid construction. A touch expensive but worth it for special occasions. Good smoke!