Description
A Time Capsule from Havana’s Best Year
I still remember the buzz in 2011 when Habanos S.A. announced they were releasing a Gran Reserva Sir Winston. That’s not just any release – it’s aged tobacco from the exceptional 2006 harvest, given an additional five years to rest before being rolled into what might be H. Upmann’s most prestigious vitola. Most Cuban cigars you find at your local shop have maybe two years on them if you’re lucky. These? They had five years minimum before they even left the factory. And now, over a decade later, we’re talking about a cigar that’s been aging longer than some aficionados have been smoking. I’ve had the privilege of smoking a few of these beauties over the years, and each time I’m reminded why the Gran Reserva designation is reserved for truly exceptional tobacco. You’re not just buying a Cuban cigar when you order one of these – you’re getting a piece of Habanos history, rolled in one of Churchill’s favorite sizes, from one of Cuba’s most reliable brands.
What Makes This Smoke Different
H. Upmann has been around since 1844, making it one of the oldest cigar brands still in production. Thing is, they’ve always been the gentleman’s choice – refined, elegant, never shouting for attention. The Gran Reserva Sir Winston 2011 takes everything that makes H. Upmann special and amplifies it through extended aging. Habanos only produces Gran Reserva cigars when they have tobacco that’s genuinely exceptional – we’re talking top-tier leaves from Vuelta Abajo that showed such promise they set them aside for this exact purpose. The Sir Winston vitola itself is a monster at 7 inches with a 47 ring gauge, giving you easily two hours of smoking time, probably closer to two and a half if you’re savoring it properly. This isn’t your everyday smoke. Not even close. This is what you break out when you land that promotion, celebrate a milestone anniversary, or finally finish renovating that basement humidor you’ve been working on for six months. The target smoker? Someone who appreciates nuance over power, someone willing to dedicate an entire evening to one exceptional cigar, someone who gets why aging matters.
| Specification | Details |
|---|---|
| Vitola | Sir Winston (Churchill) |
| Length | 7 inches / 178 mm |
| Ring Gauge | 47 |
| Wrapper | Cuban Vuelta Abajo (2006 harvest) |
| Binder | Cuban Vuelta Abajo |
| Filler | Cuban Vuelta Abajo blend |
| Strength | Medium to Medium-Full |
| Smoking Time | 140-160 minutes |
The Experience: From First Light to Final Inch
Before you even light this thing, spend some time with the cold draw. I’m serious – don’t rush this part. You’ll pick up sweet hay notes, maybe some cocoa, and this subtle floral quality that tells you immediately this isn’t your standard production cigar. The wrapper has this beautiful oily sheen to it, Colorado in color with maybe some reddish tones depending on how the light hits it. Construction is flawless – I mean, you’d expect nothing less from a Gran Reserva release, but still. The cap cuts cleanly, the bunch is firm without being tight.
First third comes alive with toasted almonds and cream. That’s the immediate impression – smooth, almost gentle, but with enough complexity that you’re already paying attention. There’s cedar in the background, some white pepper on the retrohale that’s more suggestion than statement. The burn line stays razor-sharp, which always makes me happy. Ash holds for a solid inch and a half before I even think about tapping it off. What strikes me most in this early stage is the refinement – nothing harsh, nothing demanding your attention with brute force. Just layer after layer of subtle flavors building on each other.
Second third is where the aging really shows its worth. The profile deepens – you start getting leather notes, some coffee, maybe dark chocolate if you’re retrohaling consistently. Actually, scratch that – definitely dark chocolate, the expensive single-origin stuff, not the candy bar variety. The strength builds to a solid medium-full, but it’s never overwhelming. I’ve smoked regular production H. Upmann Sir Winstons, and they’re good cigars, don’t get me wrong. But this? The additional aging rounds off any rough edges while intensifying the core flavors. There’s also this subtle honey sweetness that weaves through everything – not cloying, just enough to balance the earthier notes. The smoke output is generous, creamy texture coating your palate.
Final third brings some spice back into the equation, but it’s integrated beautifully with everything else. You’ve got espresso, dark earth, a touch of cinnamon maybe? The leather notes intensify. Some cigars get harsh or bitter in the final stretch – not this one. It stays refined right down to the nub. I usually set a cigar down with maybe an inch left, but with these Gran Reservas, I find myself smoking them until my fingers get warm. The retrohale in this final stage is sublime – all the complexity of the earlier stages concentrated and amplified. Construction never wavers, burn stays even, and you’re left wishing it were just a little bit longer because you’re not ready for it to end.
How Does It Stack Up?
| Cigar | Strength | Smoking Time | Best For |
|---|---|---|---|
| H. Upmann Gran Reserva Sir Winston 2011 | Medium-Full | 140-160 min | Special occasions, extended contemplation |
| Cohiba Behike 56 | Medium-Full | 90-110 min | When you want complexity with more punch |
| Montecristo A | Medium | 120-140 min | Classic large format experience |
What to Drink With It
I’ve paired this cigar with everything from aged rum to single malt scotch, and honestly? It works with all of it. But my favorite pairing – and I know some guys at the lounge think I’m crazy for this – is actually a good Cognac. Something like Rémy Martin XO or Hennessy Paradis if you’re really going all out. The grape and oak notes in the Cognac mirror the complexity in the cigar without overwhelming it. If you’re a whisky person, go for something Speyside – Glenfiddich 18 or Macallan 18 would be phenomenal. The sherry cask aging plays beautifully with the tobacco. For rum lovers, Zacapa 23 or Diplomatico Reserva Exclusiva are solid choices. I had one of these at an LCDH in Mexico with a glass of aged Guatemalan rum, and I’m pretty sure that’s what they serve in heaven. Coffee works too – a proper Cuban coffee or a rich cappuccino if you’re smoking this in the afternoon. As for occasions? This is your trophy cigar. Wedding, anniversary, birth of a child, closing that big deal. Not a Tuesday after work smoke, unless you’ve had one hell of a Tuesday.
What You’re Probably Wondering
How long can I age these cigars further?
These are already beautifully aged, but yes, you can continue aging them if your humidor conditions are dialed in properly. I’ve heard from collectors who’ve held onto their 2011 Gran Reservas and they just keep getting better – the flavors meld even more over time. Just keep them at 65-68% humidity and around 65-68°F, and check on them periodically. That said, they’re smoking gorgeously right now, so there’s no wrong answer here.
What’s the difference between Gran Reserva and Reserva releases?
Gran Reserva uses tobacco aged minimum five years before rolling, while Reserva uses tobacco aged minimum three years. Both get special secondary bands and limited production runs, but Gran Reservas are the top tier. Habanos is picky about these releases – they only do them when the tobacco quality justifies it, which is why you don’t see them every year. The additional aging time really does make a noticeable difference in complexity and smoothness.
Should I smoke this right away or let it rest after shipping?
Let it rest, no question. Even though these cigars are incredibly well-aged, shipping can stress them out – temperature fluctuations, humidity changes, getting jostled around. Give them at least two weeks in your humidor to recover, preferably a month if you can wait. I know it’s tempting to light one up immediately when that box arrives, but trust me on this. The cigar will thank you for the patience.
How does this compare to a regular production H. Upmann Sir Winston?
It’s like comparing a good bottle of wine to a great bottle from an exceptional vintage year. The regular Sir Winston is a solid cigar – I keep them in my rotation and enjoy them regularly. But the Gran Reserva has this extra dimension of complexity and refinement that the additional aging provides. Smoother, more integrated flavors, better balance. Both are worth smoking, but the Gran Reserva is something special.
Why is the ring gauge smaller than modern Churchill sizes?
The 47 ring gauge is actually the traditional Churchill specification – it’s what the vitola was originally. Modern trend has pushed Churchill sizes bigger, with some hitting 50 or even 52 ring gauge, but the classic proportion is 7×47. Personally, I prefer it this way – you get more wrapper-to-filler ratio, which means the wrapper influence comes through stronger in the flavor profile. Plus it’s a bit easier to smoke for the full two-plus hours without fatigue.
Are these cigars guaranteed authentic?
When you order from legitimate sources like finestcigars and other authorized dealers, absolutely. These Gran Reserva releases come with special bands and packaging that are difficult to counterfeit, plus reputable sellers have direct relationships with official distributors. That guarantee of authenticity is crucial with ultra-premium Cuban cigars – there are fakes out there, but stick with established retailers and you’ll be fine. Check that the secondary Gran Reserva band is properly affixed and that the box codes match up.
What’s the best way to store these long-term?
If you’re planning to hold onto these for years, consistency is everything. Keep them in a quality humidor – not a desktop cheapie, but something with good seal and reliable hygrometer. Boveda packs at 65% work great for aged Cubans. Keep the box they came in if possible, as the factory boxes provide good protection. Store them away from light, maintain stable temperature, and resist the urge to handle them constantly. I rotate my aged stock to the back of my cabinet so I’m not tempted to dig into them every time I open the humidor.
The Bottom Line
The H. Upmann Gran Reserva Sir Winston 2011 is everything a ultra-premium Cuban cigar should be – impeccably constructed, beautifully aged, complex without being overwhelming, and refined in a way that only extended aging can achieve. This isn’t a cigar for building a rotation around, but rather one to order for those moments when only something truly exceptional will do. Whether you’re celebrating a personal milestone or simply want to experience what properly aged Cuban tobacco can achieve, this checks all the boxes. The information in this review comes from personal experience and consistent observations across multiple examples – these cigars deliver quality with remarkable consistency. Don’t sleep on the opportunity to acquire cigars from this legendary release list. Add one to your humidor, pick the right occasion, pair it properly, and dedicate an evening to the experience. That’s my recommendation, and I’m sticking to it.
