H. Upmann Gran Reserva Sir Winston 2011 is the brand's first ever Gran Reserva and one of the most sought-after Cuban Churchills. This mild to medium 7.0" x 47 Churchill delivers orange peel, cocoa and creamy marzipan. Recommended for collectors who value refinement and provenance. Learn more →
Gran Reserva is one of Cuba's most storied marcas — every cigar hand-rolled in Havana from sun-grown Vuelta Abajo leaf, aged and crafted by master torcedores under the official Habanos S.A. seal.
It's not just a cigar. It's an experience reserved for the true connoisseur.
Explore Gran Reserva
Every H. Upmann Gran Reserva Sir Winston 2011 is guaranteed 100% authentic, sourced directly from Habanos S.A. with the official seal and full traceability from Vuelta Abajo to your door.
The H. Upmann Gran Reserva Sir Winston 2011 is one of the most coveted releases ever to carry the venerable H. Upmann name, marking the very first Gran Reserva the brand committed to its catalogue. Unveiled at the Festival del Habano and reaching collectors in numbered black lacquer boxes, this Churchill is built entirely from leaves harvested in 2011 in the Vuelta Abajo region of Pinar del Río, the heartland of Cuban tobacco. Every component, from filler to binder to wrapper, was rested through a long five year aging process before rolling, which is precisely what the Gran Reserva designation promises. The result is a cigar that feels less like a smoke and more like an occasion.
The opening third leans elegant and composed, with bright orange peel and citrus sitting over a base of cocoa and gentle leather. As the burn settles into the middle third, the smoke thickens and turns creamier, bringing forward marzipan, milk chocolate and toasted pecan alongside a soft baking spice warmth. White pepper threads through the retrohale while a caramel sweetness lingers on the palate, and the final third holds its mellow, refined character rather than charging toward power. Throughout, this is a cigar that rewards patience over intensity.
Although the tobacco already carries years of careful maturation behind it, the Sir Winston Gran Reserva continues to reward cellar time, with its citrus edges softening and the chocolate and nut tones growing rounder over the years. Keep it at roughly 65 to 70 percent relative humidity and a steady temperature near 18 degrees Celsius, ideally in a well seasoned humidor. Because these boxes were produced in strictly limited numbers, many owners treat them as long term holdings, and proper storage protects both the smoking experience and the value.
This is a cigar for the smoker who prizes subtlety, balance and provenance over raw strength. Its mild to medium body makes it approachable enough to enjoy without years of palate training, yet the depth and complexity reward the seasoned aficionado who can read its quiet transitions. It also makes a memorable gift or a centerpiece for a milestone celebration, given its rarity and the prestige of being H. Upmann’s debut Gran Reserva.
What size is the H. Upmann Sir Winston Gran Reserva 2011?
It is a Churchill measuring 7.0 inches (178 mm) with a 47 ring gauge, packaged in numbered boxes of 15.
How strong is this cigar?
It sits in the mild to medium range, prized for its smoothness and refinement rather than for heavy intensity.
What makes it a Gran Reserva?
It was H. Upmann’s first ever Gran Reserva, built from select 2011 Vuelta Abajo tobacco with all leaves aged for around five years before rolling.
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 Wikipedia, the official Habanos S.A. site.
Customer Reviews
Top-tier quality from H. Upmann. The H. Upmann Gran Reserva Sir Winston 2011 showcases everything I love about Cuban cigars - impeccable craftsmanship, smooth draw, and layers of flavor. Picked up notes of cocoa and pepper. Burned evenly throughout. A must-try for any serious aficionado!
Decent cigar but not my favorite from H. Upmann. The H. Upmann Gran Reserva Sir Winston 2011 has good flavor - cedar and spice - 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.
The H. Upmann H. Upmann Gran Reserva Sir Winston 2011 is a quality cigar. Nice balance of flavor and strength. I enjoyed the nuts and earth notes throughout. Construction was very good with only one minor touch-up needed. Good cigar for experienced smokers.
Phenomenal smoke! Been enjoying Cuban cigars for years and this H. Upmann Gran Reserva Sir Winston 2011 is easily one of my favorites. Beautiful wrapper, flawless construction, and about 83 minutes of pure enjoyment. The flavor profile is incredible - honey and tobacco. Will definitely order more!
Phenomenal smoke! Been enjoying Cuban cigars for years and this H. Upmann Gran Reserva Sir Winston 2011 is easily one of my favorites. Beautiful wrapper, flawless construction, and about 56 minutes of pure enjoyment. The flavor profile is incredible - nuts and earth. Will definitely order more!
Incredible cigar! The H. Upmann Gran Reserva Sir Winston 2011 from H. Upmann is absolutely exceptional. Smooth, complex, and beautifully balanced. Got wonderful notes of leather and wood throughout the smoke. Lasted about 65 minutes. Already ordering another box!
Great cigar! H. Upmann H. Upmann Gran Reserva Sir Winston 2011 offers excellent quality and flavor. Notes of nuts and earth throughout, good burn, nice draw. Not quite perfect but very close. Will definitely order again!
Phenomenal smoke! Been enjoying Cuban cigars for years and this H. Upmann Gran Reserva Sir Winston 2011 is easily one of my favorites. Beautiful wrapper, flawless construction, and about 69 minutes of pure enjoyment. The flavor profile is incredible - honey and tobacco. Will definitely order more!
Best cigar I've had in a long time! H. Upmann really knocked it out of the park with the H. Upmann Gran Reserva Sir Winston 2011. Rich flavor profile featuring cedar and spice, perfect draw, and excellent burn. Can't recommend this enough!
Top-tier quality from H. Upmann. The H. Upmann Gran Reserva Sir Winston 2011 showcases everything I love about Cuban cigars - impeccable craftsmanship, smooth draw, and layers of flavor. Picked up notes of nuts and earth. Burned evenly throughout. A must-try for any serious aficionado!
Best cigar I've had in a long time! H. Upmann really knocked it out of the park with the H. Upmann Gran Reserva Sir Winston 2011. Rich flavor profile featuring coffee and cream, perfect draw, and excellent burn. Can't recommend this enough!
Very good cigar. The H. Upmann H. Upmann Gran Reserva Sir Winston 2011 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.
Absolutely love this H. Upmann Gran Reserva Sir Winston 2011! H. Upmann continues to impress with their quality. Wonderful complexity with leather and wood, smooth creamy smoke, and perfect construction. One of my all-time favorites!
Incredible cigar! The H. Upmann Gran Reserva Sir Winston 2011 from H. Upmann is absolutely exceptional. Smooth, complex, and beautifully balanced. Got wonderful notes of honey and tobacco throughout the smoke. Lasted about 84 minutes. Already ordering another box!
Very good cigar. The H. Upmann H. Upmann Gran Reserva Sir Winston 2011 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.
A true masterpiece from H. Upmann. This H. Upmann Gran Reserva Sir Winston 2011 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!
Really enjoyed this H. Upmann Gran Reserva Sir Winston 2011. H. Upmann consistently delivers quality and this is no exception. Good complexity with notes of cedar and spice. Construction was solid and burn was even. A bit pricey but you get what you pay for with Cuban cigars. Recommended!
A true masterpiece from H. Upmann. This H. Upmann Gran Reserva Sir Winston 2011 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!
Really enjoyed this H. Upmann Gran Reserva Sir Winston 2011. H. Upmann consistently delivers quality and this is no exception. Good complexity with notes of cedar and spice. Construction was solid and burn was even. A bit pricey but you get what you pay for with Cuban cigars. Recommended!
Good cigar but expected a bit more for the price. The H. Upmann H. Upmann Gran Reserva Sir Winston 2011 delivered on flavor (cocoa and pepper) and construction, but lacked the complexity I was hoping for. Solid smoke, just not outstanding. Still enjoyable.
The H. Upmann Gran Reserva Sir Winston 2011 is a respectable cigar. Nice notes of cocoa and pepper, decent construction. However, I found it a bit one-dimensional compared to other H. Upmann offerings. Not bad, but there are better options in this price range.
Good cigar but expected a bit more for the price. The H. Upmann H. Upmann Gran Reserva Sir Winston 2011 delivered on flavor (cocoa and pepper) and construction, but lacked the complexity I was hoping for. Solid smoke, just not outstanding. Still enjoyable.
Top-tier quality from H. Upmann. The H. Upmann Gran Reserva Sir Winston 2011 showcases everything I love about Cuban cigars - impeccable craftsmanship, smooth draw, and layers of flavor. Picked up notes of honey and tobacco. Burned evenly throughout. A must-try for any serious aficionado!
Best cigar I've had in a long time! H. Upmann really knocked it out of the park with the H. Upmann Gran Reserva Sir Winston 2011. Rich flavor profile featuring cedar and spice, perfect draw, and excellent burn. Can't recommend this enough!
Showing 24 Of 72 Reviews
Show More ReviewsReviewing H. Upmann Gran Reserva Sir Winston 2011
“Exceptional selection and the cigars are genuine Habanos — correct bands, codes and a flawless draw. Shipping was fast and everything arrived in perfect condition.”
“The best online experience for Cuban cigars I have found. You can tell they care about quality and service from the first email to delivery.”
“Beautiful packaging, perfect humidity and the cigars are always flawless. After three orders this is my trusted source for Habanos.”
“Ordered a full box and it cleared customs in three days with zero issues. Fresh, well-humidified and exactly as described.”
“Discreet packaging, excellent communication and authentic cigars every time. Highly recommended for any collector.”
You must be of legal age to buy tobacco products. By continuing you confirm you are at least 21.
Cuban Cigar Online sells premium tobacco products intended for adults only.
Sorry, you must be 21 or older. This website is for adults of legal age. Please come back when you are 21.
