H. Upmann Gran Reserva Sir Winston 2011

Description

The amber light of a perfect autumn evening filtered through the windows of my favorite cigar lounge, casting long shadows across the worn leather armchairs. I’d been saving something special in my humidor for months, waiting for exactly this kind of moment when time seemed to slow down and the world outside could wait. Tonight called for the H. Upmann Gran Reserva Sir Winston 2011, one of just 5,000 numbered boxes ever produced and a testament to what happens when Cuban tobacco artistry meets patient aging.

Settling into my usual corner spot, I couldn’t help but admire the dark lacquer box before opening it. There’s something almost ceremonial about unwrapping a cigar that’s been over a decade in the making, from the 2011 harvest in Vuelta Abajo to its eventual release in 2018. The anticipation builds with each moment.

This isn’t just another Cuban cigar – it’s a celebration of H. Upmann’s legacy wrapped in tobacco that was aged a minimum of five years before ever seeing the inside of those distinctive black boxes. When you’re looking at a $100 per stick investment, you want to know exactly what you’re getting into. After spending considerable time with this Churchill, I can honestly say it lives up to every bit of the mystique surrounding the Gran Reserva releases.

Flavor Profile: A Journey Through Three Distinct Acts

The moment I lit up this Sir Winston, I was greeted by something I wasn’t entirely expecting. The dominant flavor in the first third hit me with distinct orange peel notes – bright, zesty, almost citrusy in a way that immediately set this apart from other cubans in my regular rotation. Beneath that primary note, I detected layers of creamy almonds, supple leather, and an interesting celery-like freshness that kept things lively.

What really impressed me during those opening minutes was how the cold draw had already hinted at this complexity. Sweet orange peel, cocoa nibs, that unmistakable barnyard character you get from aged Cuban tobacco, and even some ground coffee aromatics. The retrohale delivered a beautiful combination of white pepper and caramel candy sweetness that made me slow down and savor each puff.

The Second Act Transformation

Around the halfway point, this cigar completely shifted gears. The orange peel stepped back and allowed a rich, creamy peanut butter flavor to take center stage. I’ve smoked hundreds of cigars, but this particular flavor transition caught me off guard in the best possible way. There was also this cranberry tartness that appeared almost exclusively on the finish – tart, bright, and perfectly balanced against the nuttiness.

The supporting cast during this middle section included nutmeg, baker’s spices that reminded me of fresh cinnamon rolls, leather, milk chocolate, and espresso bean notes. Every draw seemed to reveal another layer, and the caramel sweetness on the retrohale remained consistent throughout. This is where the cigar truly showed its pedigree – the complexity was insane, and I found myself taking notes just to keep track of everything I was experiencing.

The Final Third: All Elements Converge

As I entered the final stretch, the cigar brought together most of the flavors I’d encountered earlier, though with less distinct separation. The peanut butter, orange peel, and cranberry notes mellowed considerably, allowing the leather, cocoa nibs, and fresh espresso to shine through more prominently. The caramel candy sweetness became more noticeable on the retrohale, creating this beautiful dessert-like finish that carried me right to the nub.

What struck me most about this final third was how well-integrated everything became. Rather than individual flavor notes competing for attention, they melded into this cohesive, sophisticated profile that spoke to both the quality of the tobacco and the skill of the torcedores who crafted it.

Construction and Appearance: Museum-Quality Craftsmanship

The wrapper on this Sir Winston Gran Reserva is absolutely gorgeous – a rich, oily colorado shade with minimal veining and a silky texture that feels substantial without being thick. At 7 inches long with a 47 ring gauge, it’s got that classic Churchill presence that demands respect. The cap was perfectly applied, and I didn’t find any soft spots along the entire length of the cigar.

This particular vitola uses the factory designation Julieta No. 2, and you can tell immediately that these received extra attention during production. The construction was flawless throughout my smoking session – even burn line, excellent draw resistance, and that telltale Cuban density that speaks to proper aging and fermentation. Using tobacco from Cuba’s renowned Vuelta Abajo region, specifically from the 2011 crop, gives this cigar a foundation that’s simply unmatched.

The ash held firm for well over an inch at a time, displaying that classic light gray color with clean lines. No touch-ups required, no burn issues whatsoever. When you’re dealing with tobacco that’s been aged this long, the construction tends to be bulletproof, and this Gran Reserva proved that point beautifully.

Technical Specifications

Who This Cigar Is Best Suited For

This isn’t a cigar for beginners, and I don’t say that to be elitist – it’s simply a matter of appreciation. The Sir Winston Gran Reserva requires a developed palate to truly understand what’s happening throughout the smoking experience. If you’re someone who can pick out individual flavor notes and enjoys the journey of a slowly evolving profile, this is absolutely worth the investment.

I’d recommend this to experienced Cuban cigar enthusiasts who understand the difference that proper aging makes. The pleasant smoking format and handmade construction make it perfect for special occasions – anniversaries, promotions, or those rare evenings when you want to celebrate something significant. It’s also ideal for collectors who appreciate limited releases and want something truly unique in their humidor.

Given the price point and rarity, this is definitely a special occasion cigar. I wouldn’t suggest it as a daily smoke, but for those moments when you want to experience what Cuban tobacco artistry can achieve at its absolute peak, there are few cigars that deliver this level of complexity and refinement.

Perfect Pairings: Elevating the Experience

The complexity of this Gran Reserva opens up some incredible pairing opportunities. My personal favorite has been a quality aged rum – specifically something like Diplomático Reserva Exclusiva or Mount Gay XO. The caramel and vanilla notes in these rums complement those caramel candy sweetness notes on the retrohale beautifully.

For whiskey lovers, I’ve found that a smooth single malt Scotch works wonderfully, particularly something from Speyside like Glenfiddich 18 or Macallan 15. The nutty, honeyed characteristics of these whiskies pair exceptionally well with those peanut butter and almond flavors in the second third.

Coffee and Wine Options

If you prefer non-alcoholic pairings, a rich espresso or Cuban coffee enhances those espresso bean notes beautifully. For wine enthusiasts, I’ve had great success with a full-bodied Cabernet Sauvignon or even a vintage Port – something with enough body to stand up to the cigar’s complexity without overwhelming those delicate citrus notes.

Whatever you choose, make sure it’s something you can sip slowly. This cigar demands patience and attention, and your pairing should complement that leisurely pace rather than rush the experience.

Storage Requirements and Aging Potential

These Gran Reserva cigars require careful storage to maintain their peak condition. I keep mine at 65-68% humidity and 68-70°F temperature. The tobacco has already been aged extensively, but I’ve found that an additional year or two of proper storage in your own humidor can add even more complexity to the profile.

Given the rarity and investment involved, I strongly recommend storing these in individual tubes or carefully separated from your regular rotation. The oils in the wrapper are still active, and proper storage techniques will ensure you get the full experience when you’re ready to smoke them.

I’ve noticed that cigars from this 2011 cosecha continue to evolve beautifully with time. The integration of flavors becomes even smoother, and some of those sharper citrus notes mellow into something even more refined. If you have the patience and proper storage conditions, these cigars can continue improving for several more years.

Proper Cutting and Lighting Techniques

With a cigar of this caliber, your cutting and lighting technique becomes crucial. I always use a sharp guillotine cutter and make a clean cut about 1/8 inch from the cap. The construction is solid enough to handle a straight cut without any concerns about unraveling.

For lighting, take your time with a butane torch or cedar spills. Toast the foot evenly, rotating the cigar slowly to ensure an even light. Don’t rush this process – a poorly lit premium cigar is a waste of both time and money. The initial light sets the stage for everything that follows.

Once lit, resist the urge to puff too frequently. This cigar rewards patience and performs best with draws spaced about 45-60 seconds apart. For more detailed guidance on proper techniques, check out this comprehensive guide on mastering Cuban cigar smoking.

Authenticating Your Gran Reserva

With cigars this rare and expensive, authentication is crucial. Genuine H. Upmann Sir Winston Gran Reserva 2011 boxes come with specific Habanos authentication features including holographic seals and numbered certificates. The black lacquer boxes themselves are distinctive and high-quality, not something that’s easily replicated.

Each individual cigar should have a perfectly applied band with sharp printing and proper alignment. The wrapper should have that characteristic oily sheen and the construction should feel substantial without any soft spots. When in doubt, purchase from authorized dealers who can guarantee authenticity.

The cigars themselves have a distinctive aroma even before lighting – that combination of aged tobacco, sweet hay, and subtle barnyard notes that only comes from properly fermented Cuban leaf. If something seems off about the appearance, aroma, or construction, trust your instincts.

Frequently Asked Questions

How does this compare to regular production H. Upmann Sir Winston cigars?

The Gran Reserva version uses tobacco that’s been aged significantly longer than regular production cigars. This extended aging creates much more complex flavor development and smoother integration. While regular Sir Winstons are excellent cigars, the Gran Reserva represents a completely different level of refinement and complexity.

Is this cigar worth the premium price?

For collectors and serious Cuban cigar enthusiasts, absolutely. The combination of limited production (only 5,000 boxes worldwide), extended aging, and exceptional complexity justifies the investment. However, if you’re new to premium cigars or looking for regular smoking material, there are more cost-effective options that would better suit your needs.

How long can I store these cigars before they peak?

These cigars are already smoking beautifully, but they have excellent aging potential. With proper storage at 65-68% humidity, they can continue developing for another 5-10 years or more. Many collectors find that Cuban cigars from exceptional vintages like 2011 reach their absolute peak around 15-20 years of total age.

What makes the 2011 vintage special?

The 2011 crop from Cuba’s Vuelta Abajo region benefited from ideal growing conditions that year. The tobacco showed exceptional character from the start, which is why it was selected for the Gran Reserva treatment. Combined with the minimum five-year aging process before release, this creates a truly exceptional smoking experience.

Should I smoke this cigar now or continue aging it?

This really depends on your personal preferences and patience level. The cigar is smoking fantastically right now and delivers everything you’d expect from a Gran Reserva release. However, if you enjoy the process of aging cigars and have proper storage conditions, another few years could add even more depth and integration to the profile. I’d suggest buying multiple cigars if possible – smoke one now and age the others to compare how they evolve.

Whether you’re a seasoned collector adding to your finest cigars collection or someone looking to experience what Cuban tobacco craftsmanship can achieve at its absolute pinnacle, the H. Upmann Gran Reserva Sir Winston 2011 delivers an unforgettable smoking experience. From that distinctive orange peel opening to the beautifully integrated final third, every moment with this cigar reinforces why certain releases become legendary among enthusiasts.