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HomeSpecial CollectionsVintageH. Upmann Gran Reserva Sir Winston 2011
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H. Upmann Gran Reserva Sir Winston 2011 - High Resolution
H. Upmann Gran Reserva Sir Winston 2011 Cuban Cigar - Image 1
H. Upmann Gran Reserva Sir Winston 2011 Box View - Authentic Habanos
H. Upmann Gran Reserva Sir Winston 2011 - High Resolution
H. Upmann Gran Reserva Sir Winston 2011 Cuban Cigar - Image 1
H. Upmann Gran Reserva Sir Winston 2011 Box View - Authentic Habanos
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In stock

Vintage

H. Upmann Gran Reserva Sir Winston 2011

Rated 4.6 out of 5 based on 5 customer ratings

$1,347.00

The H. Upmann Sir Winston Gran Reserva Cosecha 2011 is a rare and exquisite limited edition Cuban cigar. Uncover its rich history, unique characteristics, and enticing flavor profile, making it a must-try for cigar enthusiasts.

Feature Description
Brand H. Upmann
Line Sir Winston
Edition Gran Reserva Cosecha 2011
Vitola Churchill
Size 7 x 47
Wrapper Cuban
Binder Cuban
Filler Cuban
Strength Medium
Flavor Profile Cocoa, citrus, sweet spices, nuttiness
Smoking Time 60-90 minutes
Box Size 15 cigars
Tobacco Origin Pinar del Río, Cuba
Harvest Year 2011
Aging Minimum 5 years
Production Limited edition
Availability Cuban Cigar For Sale, authorized Habanos distributors, reputable online retailers
Pairing Suggestions Aged rum, single malt Scotch, robust coffee
Construction Excellent, flawless wrapper
Draw Smooth and effortless
Burn Even
Rarity High
Price Point Premium
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Description

Description

H. Upmann Sir Winston Gran Reserva Cosecha 2011 Review We’re stuck in time, and you know it better than anyone. I had not held a cigar in almost three years. It wasn’t a health kick, exactly, and it wasn’t some grand moral stand — I just woke up one Tuesday in 2021 and decided that I’d had enough of the ash and the lingering scent of cedar on my jackets.

Product Specifications

Attribute Detail
Product Name H. Upmann Sir Winston Gran Reserva Cosecha 2011
Origin Cuba
Factory n/a
Vitola Churchill
Length 178 mm (7 inches)
Ring Gauge 47
Wrapper Cuba (Vuelta Abajo)
Binder Cuba (Vuelta Abajo)
Filler Cuba (Vuelta Abajo)
Strength Medium

I folded the cutters up and put them in a drawer, gave my humidors to my brother and walked away. But life has a way of coming around on you. Last week, I was once again in my father’s former study. You know the type of room — a big, old heavy mahogany desk, wall-to-wall floor to ceiling bookshelves filled with books nobody has read since the seventies and that thick permanent smell of ancient leather and pipe tobacco that makes you feel like it’s soaking into your pores every time you walk through the door.

I was there to clean up a few files, but the air in that room got to me. I had this odd, twitchy energy. My heart was pounding, not from anxiety but from a sort of flashbulb recognition that I was over my break. I did not want a cigarette and I did not want to drink.

I craved a few minutes of thoughtful stillness that only the long-enduring, slow-burning stick can supply. I reached into the back of his desk drawer — the “secret” one he thought I didn’t know about — and my fingers brushed against a sleek, black lacquered box. I took it out, and a green reflection gleamed from the gold lettering under the light of the banker’s lamp. It was a box I had given him years before that he’d never used.

A time capsule from 2011. That smoke? The
H. Upmann Sir Winston Gran Reserva Cosecha 2011 #4 H.Upmann Sir Winston The 2011 release of the Gran Reserva is characterized by an even delivery and exceptional flavour consistency; a selection that honors H.Upmann legacy with taste, elegance and complexity in abundance.
.

I thought that if I was going to break a three-year fast, at least I’d be breaking it with to something that had been waiting for me as long as I’d been gone. The Specs
Attribute
Detail
Vitola de Galera
Julieta No. 2 (Churchill)
Tobacco Origin
2010 Crop, Harvested 2011
Construction: A Five-Year Nap
I’m not going to lie, holding a Churchill for the first time in three years of nothing feels major.

It’s a lot of cigar. This is not one of those quick lunch-break smokes; this finds you signing your life away for two hours. This Gran Reserva has some wrapper on it. It’s got that classic Cuban sheen— it ain’t oily like a Broadleaf, but instead is more of a matte, silky texture that feels like expensive stationery under your thumb.

The tobacco was harvested in 2011, rested for at least five years before it even got to a rolling table and the leaves look ), well settled is how one might describe how they look. No meathooks to follow, no soft underbelly. Just a solid, uniform roll. I cut the cap with an old double-guillotine that I had found in a pencil cup.

The pre-light draw was literally H. Upmann to me.Open and loose with just the right amount of resistance, letting you know it’s good for something. There were notes of cold hay, and a little of that “barnyard” funk that lets you know the fermentation was done right. It had weight in the hand, both solid and balanced.

I leaned back in my dad’s leather chair, its springs whining beneath me, and toasted the foot. I wasn’t rushing. When you’ve already been waiting three years, there’s no harm in another thirty seconds of toasting. The First Third: The Awakening
The first few drags were like running into an old pal who had not aged a day.

The smoke output was generous. This sweet orange peel just hit me right out of the gate. It wasn’t acidic, no — more like a dried zest you’d find in an expensive chocolate bar. And speaking of chocolate, there’s a creamy milk chocolate sensation that sits right on the tip of the tongue.

It’s smooth. Real smooth. I believe that five-year aging really takes the sharp edge off some of the younger Cubans. An inch-and-a-half in, and there it was, a shimmy of cinnamon tapping around the circumference.

It’s a “hot” smoke, if that means anything. It’s not spicy like a Nicaraguan pepper-bomb, more a kitchen spice cabinet warmth. I also got a decent cedar note, which might have been from the cigar or it might have just been from sitting in a room covered with wood. Either way, the earthiness began to anchor the sweetness.

It’s MILD, an ’aight beginning and just right for my “un-virgin” lungs. I didn’t want to get put down; I wanted it introduced back into my lifestyle. The burn was a straight razor, which is always nice when you’re working with something this long. The Second Third: The Complexity Continues
Midway through this six- or seven-inch journey, the profile changed in a way that genuinely caught me off guard.

You know how sometimes one flavor just sings? For me, it was peanut butter. I know, weird for a cigar, but it was there that fatty nuttiness sitting on top of the tongue, lining its lips. But it wasn’t alone.

There was just this sharp, cranberry-like tartness that sliced right through the fat. It’s a brilliant contrast. So you’re savoring creamy nuts for a second than, bap, you’ve got this zippy fruitiness. The “baker’s spices” began to kick in here.

Nutmeg and maybe a touch of clove. That milk chocolate from the first third turned more into a espresso bean bitterness, but it just stayed underneath as a support for everything else. The hay note remained, but it was more like “sweet hay” now, a field in the sun. I have to say, the complexity was decent.

I felt as though with every few puffs I grabbed another layer. It’s a nuanced experience. It’s not a shrieker; it’s a whisperer. You need to pay attention, and that’s just what I was looking for, sitting in the stillness of the study.

Part Three: The Last Stand
Around the last couple of inches, I was feeling that same buzz from earlier in the day but with a softened edge to the nicotine. The force remained solidly in that medium realm, never venturing into “OK I need to lie down” territory. The retrohale — which I usually avoid because I’m a wimp — was surprisingly pleasant. This was pure caramel candy sweetness.

I mean thick, sweet, soft caramel that melts in your mouth. It was my best hit of the entire smoke. There was a hint of white pepper that showed up toward the end just to let me know this thing I’m smoking is, after all, still a cigar. I experienced mostly good construction, but I had to use my lighter a couple of times to retouch the burn line.

Nothing serious, just your everyday Churchill upkeep. The heat remained mild even as I approached the nub. I didn’t want to put it down. I sat in that chair until I was so close to the cherry, my fingers were almost brushing against it, savoring the last of that notes red leath

Additional information

Additional information

Taste

Earthy, Fruity, Nutty, Spicy, Woody

Reviews (5)

5 reviews for H. Upmann Gran Reserva Sir Winston 2011

  1. Rated 5 out of 5

    Benjamin Ramos – July 12, 2025

    Loyal customer! Been buying here for years. Quality and service never disappoint.
  2. Rated 4 out of 5

    Richard Hill – April 19, 2025

    Value for money! When you factor in fast shipping and authentic product, it's a great deal.
  3. Rated 5 out of 5

    Andrew Wright – January 1, 2025

    Rich and robust! Full flavor without being overpowering. Notes of cocoa, espresso, and aged tobacco.
  4. Rated 4 out of 5

    Frank Cruz – December 18, 2024

    Value for money! When you factor in fast shipping and authentic product, it's a great deal.
  5. Rated 5 out of 5

    Kenneth Reed – November 2, 2024

    Outstanding quality! From the moment I opened the box, I knew these were special. Perfect draw, beautiful wrapper, and flavors that evolve throughout the smoke. Highly recommended!

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    H. Upmann Gran Reserva Sir Winston 2011 - High Resolution
    H. Upmann Gran Reserva Sir Winston 2011
    Rated 4.6 out of 5
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