Description
The Gran Reserva Nobody Talks About Enough
Look, I’ve been smoking Cuban cigars since my first trip to Havana back in ’96 – when you could still walk into any Casa del Habano without a reservation – and I’ll be honest with you: the H. Upmann Gran Reserva Sir Winston 2011 is one of those cigars that makes me question why people obsess over certain other limited releases. This isn’t just another fancy-banded Churchill with a premium price tag. This is what happens when Habanos takes one of their most underrated brands and gives it the full royal treatment – vintage tobaccos from 2009, aged in Spanish cedar tercios, limited to just 5,000 numbered boxes worldwide. Thing is, H. Upmann doesn’t get the same hype as Cohiba or Behike, so these Gran Reservas flew under the radar for a lot of collectors. Their loss, honestly.
I remember when these first dropped in 2011. My buddy Carlos – the guy who runs a cigar club down in Miami – called me up saying “You need to get your hands on these before they disappear.” I’ll admit, I was skeptical. H. Upmann has always been that brand I respected but never got passionate about. Solid, reliable, but rarely mind-blowing. Well, I was wrong. Dead wrong.
What Makes This Churchill Special
Here’s the thing about H. Upmann – the brand dates back to 1844, making it one of the oldest Cuban cigar houses still in operation. Founded by a German banker (yeah, really) named Hermann Upmann who fell in love with Cuban tobacco, the brand built its reputation on consistency and elegance rather than power. They’ve always been the gentleman’s smoke, the refined choice. Not flashy, just impeccably constructed and nuanced.
The Gran Reserva designation means something specific in the Habanos portfolio. We’re not talking about your standard production run here. These cigars are made with tobaccos that have been aged for a minimum of three years before rolling, then the finished cigars get at least two more years of aging before they see daylight. For the Sir Winston 2011, we’re looking at leaves harvested in 2009 from the Vuelta Abajo region – the holy grail of Cuban tobacco country. Every single leaf. No filler from lesser regions, no shortcuts.
The Sir Winston vitola itself is a beast – it’s named after Churchill himself, who was famously photographed with Cuban cigars throughout his life. This format demands patience. If you’re the type who wants a quick twenty-minute smoke, keep scrolling. This is an investment of your evening, and it rewards that commitment with complexity you just don’t get from smaller formats.
Who’s this cigar for? Real talk: if you’re new to Cubans, start somewhere else. This is for the smoker who already knows they love the classic H. Upmann profile and wants to experience it at its absolute peak. It’s for the collector who appreciates that limited edition doesn’t always mean overrated. And honestly? It’s for anyone who’s gotten bored with the usual suspects and wants to rediscover why Cuban cigars earned their reputation in the first place.
| Specification | Details |
|---|---|
| Vitola | Gran Corona (Sir Winston) |
| Length | 7 inches / 178 mm |
| Ring Gauge | 47 |
| Wrapper | Cuban Vuelta Abajo (2009 harvest) |
| Binder | Cuban Vuelta Abajo |
| Filler | Cuban Vuelta Abajo long filler blend |
| Strength | Mild to Medium |
| Smoking Time | 90-120 minutes |
The Smoking Experience – And Why I Keep Coming Back
Okay, so here’s where I probably sound like every other cigar writer, but hear me out: the pre-light aroma on this thing is intoxicating. I’m not exaggerating. That cedar note hits you before you even cut it – it’s like opening a humidor that’s been perfectly maintained for a decade. There’s this underlying sweetness, almost honeyed, with just a whisper of barnyard funk that tells you this is proper Cuban leaf. The wrapper itself is gorgeous. Colorado shade, oily but not greasy, with veins that are there but not distracting. Construction? Flawless. I’ve smoked maybe six of these over the years and not once have I had to correct the burn or deal with a tight draw.
First third starts creamy. That’s the word that keeps coming back to me – creamy. There’s this buttery smoothness to the smoke that coats your palate without overwhelming it. Cedar dominates, but it’s accompanied by subtle coffee notes. Not espresso, more like a cappuccino that’s been sitting for a minute and cooled down. Mild pepper on the retrohale, nothing aggressive. The strength is deceptive here. You think “this is gentle” and then forty minutes in you realize you probably should have eaten lunch. It’s sneaky that way.
The middle section is where the vintage aging really shows up. The flavor profile deepens – that coffee note gets richer, darker, more pronounced. There’s leather now, smooth and supple, not the harsh tannic leather you get from younger cigars. Hints of dried fruit start appearing. I swear I pick up dates or figs, something with that dark sweetness. The creaminess from the first third doesn’t disappear, it just becomes a foundation for these more complex flavors to build on. And the wrapper – oh man, the wrapper – it’s got this subtle spice that tingles on your lips without being overwhelming. The burn line stays razor-sharp. The ash holds for almost two inches if you’re careful, that beautiful light gray that tells you the tobacco was perfectly fermented.
Final third is where opinions might split. Some people want cigars that go big at the end, that crescendo into this powerful finish. This doesn’t do that. The Gran Reserva Sir Winston stays true to the H. Upmann character – it gets richer, more concentrated, but never harsh. Never bitter. The pepper picks up a bit, there’s more earth in the mix now, almost cocoa-like. That cedar note that started everything comes back around, tying the whole experience together. I find myself slowing down in this section, not wanting it to end. The strength peaks at medium, maybe medium-plus if you’ve been smoking it fast. Retrohale in the final two inches and you get this amazing combination of sweet tobacco, aged wood, and just a touch of espresso bitterness that works perfectly.
No joke, the smoking time on these is something to plan for. I’ve never finished one in less than 90 minutes, and I don’t exactly smoke slow. Factor in two hours if you’re pairing it with drinks and conversation. It’s not a cigar you light up with fifteen minutes to kill before dinner.
How It Stacks Up Against Similar Limited Releases
| Cigar | Strength | Smoking Time | Best For |
|---|---|---|---|
| H. Upmann Gran Reserva Sir Winston 2011 | Mild-Medium | 90-120 min | Aficionados seeking elegance and complexity without power |
| Cohiba Behike 56 | Medium-Full | 90-110 min | Those who want richness with the Cohiba prestige factor |
| Montecristo Gran Reserva No. 2 | Medium | 80-100 min | Fans of the classic Monte profile elevated to collector status |
| Romeo y Julieta Churchill | Mild-Medium | 75-90 min | Daily smokers wanting a reliable, approachable Churchill |
Between you and me, comparing this to the Cohiba Behike feels almost unfair – they’re targeting completely different smokers. The Behike is bold, rich, demands your attention. The H. Upmann Gran Reserva is refined, subtle, rewards your attention. If you’re choosing between them, ask yourself: do you want to be impressed or do you want to be seduced? Both are exceptional cigars, but the Behike has become a status symbol in a way that sometimes overshadows the actual smoking experience. This H. Upmann? It’s all about the smoke.
The Montecristo Gran Reserva No. 2 is probably the closest comparison in terms of concept – classic brand, vintage tobacco, limited release. I’ve found the Monte to be slightly more robust, a bit more forward with its flavors. The H. Upmann takes a softer approach. If I’m honest, I reach for the H. Upmann more often because it works in more situations. The Monte demands perfect conditions and your full focus. This Sir Winston is more forgiving.
What to Drink With It (And When to Smoke It)
Coffee pairings work beautifully here, especially in the morning or early afternoon. I’m talking about a proper café con leche, not some over-roasted commodity coffee. The creaminess of the milk echoes the creamy smoke character, and the coffee’s mild bitterness plays off that cedar-leather combination perfectly. Actually, scratch that – what I mean is, save this cigar for when you’ve got time to properly enjoy it. Morning coffee might rush you.
For spirits, I’ll be blunt: aged rum is the move. A 15-year-old Cuban rum if you can source it, or something like Diplomatico Reserva Exclusiva if you can’t. The rum’s vanilla and caramel notes complement the tobacco’s natural sweetness without competing. I’ve also paired this with a slightly peated single malt – Talisker 10 specifically – and that combination was revelatory. The smoke-on-smoke thing works when both elements are subtle enough not to clash.
Thing is, this cigar also pairs exceptionally well with absolutely nothing. Sometimes the best pairing is a glass of room-temperature water to cleanse your palate between thirds. Let the tobacco speak for itself. That’s probably the most traditional approach, and with aged vintage leaf like this, it’s worth experiencing pure at least once.
Time of day? Late afternoon into evening is my sweet spot. This isn’t a morning cigar despite the mild strength – it’s too nuanced, too complex for your palate when it’s still waking up. I love this after a good meal, maybe two hours after dinner when you’ve digested enough that the nicotine won’t hit wrong. Weekend afternoons on the golf course if you’re the type who smokes while playing. Or my personal favorite: late evening on a covered porch while it’s raining. Something about that combination just works.
What People Keep Asking Me About This Cigar
How does the Gran Reserva Sir Winston 2011 differ from regular H. Upmann Sir Winston production?
The difference is night and day, honestly. Regular production Sir Winstons are excellent cigars – don’t get me wrong – but the Gran Reserva uses tobaccos that were aged for three years before rolling, then aged another two years as finished cigars. The 2011 release specifically used leaves from the 2009 harvest, exclusively from Vuelta Abajo. Regular production uses tobacco from various harvests and regions within Cuba. The flavor complexity and smoothness you get from that extra aging isn’t something you can replicate. The regular Sir Winston is reliable and enjoyable; the Gran Reserva is an event.
Can I still find the H. Upmann Gran Reserva Sir Winston 2011, and how long can I age it further?
Finding them now requires some hunting. Only 5,000 numbered boxes were produced, and we’re over a decade past release. Reputable retailers occasionally have inventory, but expect availability to be spotty. As for aging, these cigars are already performing beautifully and have been aged significantly before sale. That said, I know collectors who’ve held onto boxes and report they’re still getting better – the cedar notes become more integrated, the creaminess deepens. Cuban cigars with this level of initial aging can continue evolving for decades if stored properly at 65-70% humidity and consistent temperature. I wouldn’t age these indefinitely though – they’re meant to be smoked and enjoyed, not just collected.
Is this cigar strong enough for experienced smokers, or is it too mild?
Okay, so this is where you need to separate strength from complexity. The nicotine strength is mild to medium – it’s not going to knock you on your rear like a Partagás Serie D or a Bolivar. But complexity? This thing runs circles around cigars twice its strength. Experienced smokers who’ve matured past the “stronger equals better” phase will appreciate the nuance here. The subtlety is the point. I’ve been smoking cigars for over 25 years and I’d choose this over most full-strength offerings because the flavor development is just more interesting. If you need that nicotine punch to feel satisfied, pair it with espresso or aged rum. The vintage tobacco provides plenty of satisfaction even at moderate strength.
What’s the best way to store and maintain the H. Upmann Gran Reserva Sir Winston 2011?
These should be stored like any premium aged Cuban – consistent humidity between 65-68% and temperature around 65-70°F. I keep mine slightly drier than newer production cigars because the aged tobacco doesn’t need as much moisture to smoke well. Spanish cedar in your humidor is ideal since these cigars were aged in cedar tercios. Avoid fluctuations – that’s what kills cigars more than anything else. If you’re sitting on a full box, resist the urge to open it constantly. Let them rest undisturbed. When you do smoke one, let it acclimate to room temperature for at least thirty minutes before lighting. These cigars have been on a decade-plus journey before reaching you; don’t rush the final steps.
How does the flavor profile compare to other H. Upmann vitolas?
The classic H. Upmann character is definitely there – that creamy cedar foundation, the refined mild-to-medium profile, the elegance over power philosophy. But the Gran Reserva amplifies everything. A regular H. Upmann Magnum 46 or Half Corona gives you a sketch of the brand’s DNA; this Sir Winston gives you the oil painting. The longer smoking time of the Churchill format lets flavors develop more gradually. You get transitions you simply can’t experience in smaller vitolas. The vintage tobacco brings depth that regular production can’t match – those leather and dried fruit notes, the velvety texture of the smoke. If you’ve tried H. Upmann before and thought “nice but not exceptional,” this will change your mind. If you already love the brand, this is what you’ve been working toward.
Should I smoke this now or continue aging it in my humidor?
Not gonna lie, this is the question that keeps me up at night too. These cigars were released in 2011 with tobacco from 2009, so we’re looking at 14+ years of age already. They’re smoking phenomenally right now – I can personally attest to that. The conventional wisdom says Cuban cigars can age indefinitely with proper storage, and vintage tobaccos often have more staying power. But here’s my take: smoke one now. Experience what you have. If you’ve got a box, smoke one every year or two and track how they evolve. That’s the only way to know if further aging suits your palate. I genuinely don’t understand the mentality of aging cigars forever and never smoking them. These were made to be enjoyed. The “right time” to smoke a cigar this good is when you have two hours of uninterrupted time and something worth celebrating. Could they get better with more age? Maybe. Are they already exceptional? Absolutely.
What makes the 2011 Gran Reserva vintage special compared to other years?
The 2011 release was only the second time H. Upmann received the Gran Reserva treatment from Habanos, which makes it relatively rare in the brand’s history. The 2009 harvest that provided these leaves is generally considered an excellent vintage year in Vuelta Abajo – good growing conditions, proper rainfall, ideal fermentation weather. You can taste it in the tobacco’s natural sweetness and smoothness. Habanos doesn’t release Gran Reservas annually or even regularly; they only do it when they believe they have tobacco worthy of the designation. The fact that they chose H. Upmann in 2011 and paired it with the Sir Winston vitola was significant – they were making a statement about the brand’s place in their portfolio. Some collectors focus on the more hyped brands, but this vintage will be remembered as a highlight for H. Upmann specifically.
Final Thoughts From Someone Who’s Smoked Too Many Cigars
Look, I’m probably biased here – I have a soft spot for cigars that don’t need to shout about how good they are. The H. Upmann Gran Reserva Sir Winston 2011 is refined, elegant, and rewards patience. It’s not trying to be the strongest or the boldest. It’s content being the most sophisticated cigar in the room. The vintage aging shows in every puff, from that creamy cedar opening through the complex middle section to the satisfying finish. This is what happens when one of Cuba’s oldest brands gets the full star treatment – exceptional tobacco, meticulous aging, and a vitola that gives all those flavors room to breathe.
If you’re fortunate enough to find these still available, don’t sleep on them. Yeah, H. Upmann doesn’t have the same cachet as some other Cuban brands, but that’s actually part of the appeal. You’re not paying for hype or status symbols. You’re paying for exceptional tobacco that’s been treated with respect throughout its entire journey from field to your humidor.
And here’s what gets me: in ten more years, people will be talking about the 2011 Gran Reservas the way they now talk about vintage Dunhills or pre-embargo Cubans. The scarcity combined with the quality means these are only becoming more desirable. Whether you’re a collector looking for something special or a smoker who wants to experience Cuban cigar craftsmanship at its peak, this Sir Winston delivers. Light one up on a quiet evening when you’ve got nowhere to be and nothing to prove. That’s when this cigar makes the most sense. That’s when you’ll understand why I keep coming back to it despite having hundreds of other options in my humidor.
Trust me on this one. Or don’t, and miss out – your choice. But if you appreciate what Cuban cigars can be when everything goes right, this deserves a spot in your collection and your smoking rotation.
