H. Upmann Sir Winston

Description

The weight settles perfectly between my fingers—substantial without being unwieldy. There’s something about holding a proper Churchill that makes you slow down, almost ceremonial in the way it commands attention before you even reach for the cutter. The wrapper catches the light just so, revealing that telltale oily sheen that Cuban tobacco develops when it’s been properly aged.

I remember the first time someone handed me one of these at a lounge in London. “Try this,” he said, sliding the Sir Winston across the leather table. The band alone told the story—that familiar H. Upmann crest that’s been adorning premium cigars since 1844.

For any cigar aficionado worth their salt, the H. Upmann Sir Winston represents something special in the Cuban lineup. It’s not just another Churchill vitola; it’s a masterclass in how the Julieta No. 2 format should perform when everything comes together correctly.

Technical Specifications

Construction and Appearance

The first thing you notice when handling a genuine Sir Winston is the construction quality. The wrapper leaf displays that characteristic dark brown hue with an oily finish that speaks to proper fermentation and aging. Minimal veining runs along the surface, and when you run your fingers along the length, there shouldn’t be any hard or soft spots that indicate poor bunching.

The triple cap sits perfectly formed at the head—none of that sloppy construction you sometimes see with rushed production. This attention to detail extends throughout the entire structure, from the way the wrapper leaf spirals evenly down to the foot, to how the cigar feels balanced in your hand.

What impresses me most about the Sir Winston’s build is how it age well over time. The tobacco continues developing complexity, and that initial firmness gives way to a more supple feel after a few years in proper storage. It’s easily one of the better-constructed Churchill vitola cigars in the H. Upmann release list.

Flavor Profile Journey

First Third: The Opening Act

The initial draw delivers exactly what you’d expect from quality Cuban tobacco—strong wood notes that immediately establish the cigar’s character. There’s an intense tobacco presence that doesn’t overwhelm, balanced beautifully with rich black coffee undertones. What catches me off guard every time is how the earthiness mingles with unexpected floral notes.

The spices build gradually, never aggressive, while hints of grass add a fresh quality that keeps things interesting. Cream and hazelnut weave through the background, creating this luxurious mouthfeel. The body stays at a solid medium level, with smoke that’s remarkably silky for such a young light. The finish stretches longer than most cigars I’ve smoked in this strength range.

Middle Third: Full Development

This is where the Sir Winston really shows its pedigree. That black coffee note deepens and becomes more prominent, playing perfectly against the cream that’s now more pronounced. The wood character remains consistent, but sweet earth joins the party along with fresh herbs that add complexity without muddying the profile.

Mint appears—subtle but unmistakable—followed by roasted nuts that complement those earlier hazelnut hints. There’s a pepper presence that adds just enough bite, while vanilla rounds out the sweetness beautifully. The body builds to a solid medium-full, and the burn stays sharp with abundant aromatic smoke that fills whatever room you’re in.

Final Third: The Grand Finale

The final stretch transforms completely. Those earlier nut notes evolve into something richer and more substantial, while coffee remains a constant companion. Leather emerges—not harsh, but sophisticated—joined by sweet cedar that adds warmth to the entire experience.

The tobacco character intensifies, and you’ll notice charred aromas that speak to the cigar’s structure holding up under heat. Spice returns with more authority, and there are hints of peat and nutmeg that create genuine complexity. Graham cracker sweetness appears in the very final puffs, though by this point the body has moved to lower full territory and the overall profile is stronger and less sweet than the earlier thirds.

Perfect Pairings

In my experience, the Sir Winston demands drinks that can match its complexity without competing. A well-aged Scottish single malt like Glenfiddich 18 brings out those wood and nut characteristics beautifully. The whiskey’s honey and vanilla notes complement the cigar’s creamy middle section perfectly.

For cognac lovers, something like Hennessy XO creates an almost magical pairing. The cognac’s dried fruit and spice notes enhance the Sir Winston’s complexity, especially during that flavor-packed middle third. I’ve also found that a quality aged rum works wonderfully—the molasses sweetness plays against the cigar’s earth and coffee notes.

Coffee purists shouldn’t overlook a simple black coffee pairing, particularly a dark roast with chocolate undertones. It reinforces those coffee notes throughout the smoking experience without overwhelming the more subtle flavors. For wine enthusiasts, a full-bodied red like a well-aged Cabernet Sauvignon can hold its own against this Churchill’s intensity.

Who Should Smoke This Cigar

The Sir Winston isn’t a beginner’s cigar, honestly. Its medium to full strength and complex flavor evolution require some experience to fully appreciate. I’d recommend this to intermediate to advanced smokers who have developed their palate enough to catch those subtle transitions between thirds.

This is perfect for special occasions—celebrations, business meetings, or those quiet evening moments when you have nearly two hours to dedicate to the experience. The length and smoking time make it ideal for golf outings or long conversations on the patio.

If you’re someone who appreciates craftsmanship and doesn’t mind investing in quality, the Sir Winston delivers exceptional value for a Cuban Churchill. It’s also perfect for collectors looking to age cigars, as these develop remarkable richness over 4-5 years of proper storage.

Cutting and Lighting Technique

With that beautiful triple cap, you want to be precise with your cut. I recommend a straight cut about 2mm from the head—just enough to open the draw without damaging the wrapper construction. A sharp guillotine cutter works best; avoid punch cuts with this vitola as they can restrict the draw given the 47 ring gauge.

For lighting, take your time. The Sir Winston’s construction means it’ll light evenly if you don’t rush the process. Use a butane lighter or cedar spills, rotating slowly while toasting the foot. You want an even char across the entire surface before taking your first draw.

Once lit, this cigar burns beautifully with minimal touch-ups needed if you maintain a steady smoking pace. The ash holds well for about an inch at a time, and the burn line stays remarkably even throughout the entire smoking experience.

Storage and Aging

Proper storage makes all the difference with the Sir Winston. Maintain 65% relative humidity and keep temperatures between 65-70°F (18-21°C) for optimal performance. These cigars are incredibly rewarding to age properly—after 4-5 years, the flavors become more integrated and the overall smoking experience smooths out considerably.

I’ve found that Sir Winstons benefit from at least 6 months of rest after purchase, even if they’re already aged. The shipping and handling can affect the tobacco, and letting them settle in your humidor allows the moisture content to stabilize.

For long-term aging, store them in their original cabinet boxes when possible. The wooden boxes help maintain consistent humidity and protect the cigars from light exposure. If you’re planning to set up a humidor specifically for aging, these Churchills stack well and don’t take up excessive space despite their length.

Authentication Guide

With Cuban cigars, authenticity is crucial, and the Sir Winston is unfortunately a target for counterfeiters. Genuine examples come in varnished wooden cabinet boxes of 25 cigars with specific Habanos Packing Code CAB-VW-C/L-12,13-n-25. Check the box date codes and ensure they match Habanos records.

The cigars themselves should feel solid with no hard or soft spots when gently squeezed. The wrapper should have that oily, dark brown appearance with minimal veining. Fakes often have dry wrappers, poor construction, and inconsistent burn characteristics.

Always purchase from authorized Habanos dealers. The H. Upmann band should be crisp and properly applied, and the triple cap should be perfectly formed. If you’re unsure about authenticity, reputable dealers will provide information about their sourcing and storage practices.

Understanding the Cuban cigar production process helps identify genuine products. Legitimate Sir Winstons come from the Vuelta Abajo region where H. Upmann sources their premium tobacco.

Frequently Asked Questions

How long does an H. Upmann Sir Winston take to smoke?

Plan for 1 hour 45 minutes to 2 hours 15 minutes, depending on your smoking pace. This is a Churchill vitola, so it’s designed for a leisurely, contemplative smoking experience rather than a quick smoke.

What’s the difference between the regular Sir Winston and Gran Reserva versions?

Gran Reserva Cosecha editions use tobacco aged for additional years before rolling, resulting in enhanced smoothness with more complex flavors like leather, pepper, marzipan, and chocolate. These are limited release cigars and typically cost significantly more than the regular production Sir Winston.

Can beginners enjoy the Sir Winston?

While possible, I’d recommend building up to this cigar. The medium to full strength and 2-hour commitment can be overwhelming for new smokers. Start with milder H. Upmann offerings and work your way up to the Sir Winston as your palate develops.

How should I store Sir Winston cigars for aging?

Maintain 65% humidity and 65-70°F temperature in a quality humidor. These cigars age exceptionally well over 4-5 years, developing more integrated flavors and smoother character. Store them in their original boxes when possible to maintain consistency.

What makes the Sir Winston worth the premium price?

The combination of premium Cuban tobacco, expert construction, complex flavor development, and the prestige of the H. Upmann brand justifies the cost for serious aficionados. The smoking experience evolves significantly across the nearly 7-inch length, offering exceptional value per smoking minute compared to shorter premium cigars.

For those serious about mastering Cuban cigar appreciation, the Sir Winston represents an essential experience. It’s a cigar that rewards patience, proper storage, and careful attention to its evolving character. Whether you’re expanding your palate or celebrating a special occasion, this Churchill delivers the complexity and craftsmanship that define exceptional Cuban cigars.