Description
The Churchill That Changed Everything
I’ll never forget the first time someone handed me an H. Upmann Sir Winston. It was at a bachelor party in Miami – my buddy’s older brother pulled one out of his travel humidor and said, “You haven’t lived until you’ve tried this.” Not gonna lie, I thought he was being dramatic. But after two hours with that cigar? I got it. I finally understood what all the fuss was about.
Here’s the thing: the Sir Winston isn’t just another Churchill. It’s the Churchill that makes you rethink everything you thought you knew about H. Upmann. While the brand’s known for being mild and approachable – perfect for mornings or when you’re easing someone into Cubans – this particular vitola has a presence that demands your attention. And honestly? It deserves every minute of it.
You’re about to discover why this 7-inch giant has earned its place among the most revered Cuban cigars. We’ll walk through what makes it special, how it smokes from start to finish, and whether it’s the right fit for your humidor. Trust me, by the end of this, you’ll know exactly what to expect when you light one up.
What Makes the Sir Winston Stand Out
H. Upmann’s been around since 1844 – think about that for a second. Before the American Civil War, before Cuba even became synonymous with premium cigars, a German banker named Hermann Upmann was already rolling cigars in Havana and shipping them back to Europe. The brand’s always had this refined, almost aristocratic reputation. Mild, elegant, sophisticated. That’s the H. Upmann DNA.
But the Sir Winston? It takes that heritage and cranks it up. Named after Winston Churchill himself (who was famously devoted to cigars of this size), this vitola represents H. Upmann at its most ambitious. It’s their flagship Churchill, and they don’t mess around with it. The tobacco selection is top-tier – we’re talking Vuelta Abajo leaves from the Pinar del Río region, which is basically the Napa Valley of Cuban tobacco. You know those wrappers that make you stop and admire the cigar before you even cut it? That’s what you’re getting here.
This isn’t a cigar for rushing through your lunch break. It’s a commitment. A ritual. The kind of smoke you save for when you’ve got a free afternoon, maybe a good book, and nowhere else to be. It appeals to the smoker who appreciates nuance over punch, who’d rather spend two hours with something elegant than forty-five minutes with something aggressive. If you’re the type who gets impatient easily, well… this might test you a bit.
Technical Specifications
| Specification | Details |
|---|---|
| Vitola | Sir Winston (Churchill) |
| Length | 7 inches / 178 mm |
| Ring Gauge | 47 |
| Wrapper | Cuban (Vuelta Abajo) |
| Binder | Cuban |
| Filler | Cuban Blend (Vuelta Abajo) |
| Strength | Medium |
| Smoking Time | 90-120 minutes |
The Smoking Experience: From First Light to Final Puff
Alright, let’s talk about what actually happens when you smoke one of these. And I mean really smoke it – not rush through it while checking your phone every five minutes.
The cold draw’s the first hint that you’re in for something special. It’s easy – not too tight, not too loose (good construction right there). You’ll pick up cedar, maybe some hay, a touch of cream. Nothing aggressive. Thing is, that subtlety is intentional. H. Upmann doesn’t slap you across the face with flavors. They invite you in.
The First Third: Light it up and you’re immediately greeted with smoothness. Creamy smoke, gentle cedar notes, maybe a whisper of nuts. The burn line’s typically dead straight – these are well-constructed cigars. The ash builds white and firm, holding on for a good inch or more before you need to tap it. I’ve found the first third is all about elegance and restraint. Some people call it boring. Those people are wrong. It’s setting the stage.
The Middle Section: This is where things get interesting. Around the halfway point, the Sir Winston starts showing you what it’s capable of. The cream develops into more distinct notes – think toasted almonds, light coffee, maybe some leather. There’s a sweetness that creeps in too, kind of like honey or caramel, but it’s never cloying. The smoke gets a bit richer, more textured. But here’s the catch: it never loses that trademark H. Upmann smoothness. You’re not getting punched with nicotine or aggressive spice. It’s all about layers building on each other.
Ever noticed how some cigars just hit different when you retrohale? Try it with the Sir Winston in the second half. You’ll catch white pepper and this almost floral quality that doesn’t show up on the palate. It’s subtle – blink and you’ll miss it – but it’s there.
The Final Third: Now we’re cooking. The last portion is where the Sir Winston really earns its reputation. The flavors concentrate and deepen. That light coffee becomes espresso. The sweetness turns into dark cocoa. There’s an earthiness that emerges – not barnyard funk, just clean tobacco earthiness. And still, remarkably, it stays smooth. No harshness, no bitterness, no reason to put it down early. I’ve smoked these down to the nub more times than I can count.
The construction holds throughout. The burn might need a touch-up once or twice if you’re not paying attention (this is a long smoke, after all), but it’s never problematic. The draw stays consistent. The ash keeps building. It’s the kind of technical performance that reminds you why Cuban cigars have their reputation.
How Does It Compare?
| Cigar | Strength | Smoking Time | Best For |
|---|---|---|---|
| H. Upmann Sir Winston | Medium | 90-120 min | Long, contemplative sessions |
| Romeo y Julieta Churchill | Medium-Mild | 90-110 min | Those wanting something lighter |
| Cohiba Esplendidos | Medium-Full | 100-130 min | Special occasions, experienced smokers |
Look, if you’re trying to decide between these Churchills, here’s my take: The Romeo y Julieta’s milder and more approachable – great if you’re still building your palate. The Cohiba’s richer and fuller – amazing if you want something more robust and can handle the intensity. The Sir Winston sits right in the middle. It’s got enough complexity to keep experienced smokers engaged, but it’s not gonna overwhelm someone who’s still getting comfortable with Cuban cigars. Speaking of which, a friend of mine who’d only smoked Dominican cigars tried a Sir Winston last summer and texted me the next day asking where he could buy a box. That tells you something.
Perfect Pairings and Occasions
What are you drinking with this? Honestly, you’ve got options. My go-to is a good single malt – something like a Glenfiddich 15 or a Macallan 12. The scotch’s complexity matches the cigar’s nuance without competing with it. But here’s the truth: I’ve had amazing experiences with this cigar paired with coffee (a rich, dark roast), aged rum (think Zacapa 23), and even a good tawny port.
Cognac works beautifully too – Rémy Martin VSOP is pretty much perfect with the Sir Winston’s profile. The fruity notes in the cognac complement the cigar’s natural sweetness.
Time of day? This is an afternoon or evening smoke. You’re not lighting this up with your morning coffee (unless you’ve got a really flexible schedule). Save it for when you can dedicate two hours to it. Weekend afternoons. After a long dinner. Those rare evenings when you’ve got nothing pressing and nowhere to be.
Occasions? Celebrations, definitely. Closed a big deal? Sir Winston. Anniversary dinner wrapped up? Sir Winston. Just finished a major project? You get the idea. But don’t overthink it – sometimes the occasion is just “it’s Saturday and the weather’s nice.”
Frequently Asked Questions
How long does an H. Upmann Sir Winston take to smoke?
Plan on 90 to 120 minutes, sometimes even longer if you’re really taking your time. This isn’t a cigar you rush. I’ve had sessions go two and a half hours when I’m really savoring it. Make sure you’ve got the time before you light up – there’s nothing worse than having to put down a Sir Winston halfway through because you’ve got somewhere to be.
Is the Sir Winston too strong for beginners?
Not at all. It’s medium strength, which makes it pretty accessible. That said, the length might be challenging if you’re new to cigars – two hours is a long time when you’re not used to it. My recommendation? If you’re a beginner, try a shorter H. Upmann first (like the Half Corona or Magnum 46) to get familiar with the flavor profile, then work your way up to the Sir Winston.
What’s the best way to store these cigars?
Keep them at 65-70% humidity and around 65-70°F, same as any Cuban cigar. These need proper aging to really shine – fresh ones are good, but give them six months to a year in your humidor and they become exceptional. I’ve got a box from 2019 that’s smoking better now than when I bought it. Cuban cigars reward patience.
How does this compare to other H. Upmann vitolas?
The Sir Winston’s definitely more complex and developed than smaller H. Upmann vitolas. The Magnum 46’s great for when you want that H. Upmann character in a shorter smoke, and the Connoisseur No. 1’s excellent too, but the Sir Winston’s got this depth that comes from the longer smoking time and larger format. It’s H. Upmann showing off what they can really do.
Do I need to age Sir Winstons or can I smoke them right away?
You can smoke them fresh and they’ll be good – these are quality cigars. But aging them transforms them into something really special. I’d say minimum six months if you can wait, ideally a year or more. The flavors marry and mellow, the complexity deepens, and that signature smoothness becomes even more refined. If you buy a box, smoke one fresh to see what you’re starting with, then let the rest rest.
What time of year is best for smoking a Sir Winston?
Any time you’ve got two hours and decent weather, honestly. Spring and fall are ideal – temperatures are comfortable and you won’t be sweating or freezing. I love these on cool autumn afternoons, but I’ve also had great experiences with them on summer evenings once the heat breaks. Winter works too if you’ve got a proper smoking area. The cigar itself doesn’t care about the season – it’s more about whether you’ve got the right conditions to enjoy a long smoke.
Why is it called the Sir Winston?
It’s named after Winston Churchill, who was famously passionate about cigars of this size. The Churchill vitola itself is basically named after him because of his preference for larger ring gauge cigars around 7 inches long. H. Upmann decided to honor that connection by naming their Churchill the “Sir Winston.” It’s a fitting tribute – Churchill would’ve appreciated the elegance and quality of this particular cigar.
Final Thoughts
So, is the H. Upmann Sir Winston worth your time? If you appreciate nuanced, elegant cigars that reward patience and attention, absolutely. This isn’t the cigar that’s gonna blow you away with power or shock you with intense flavors. What it does is draw you in slowly, build complexity over time, and deliver a smoking experience that’s consistently excellent from start to finish.
Think of it this way: some cigars are like action movies – exciting, intense, memorable for the thrills. The Sir Winston’s more like a really good novel. You need to invest the time, pay attention to the details, and let it unfold at its own pace. But when you do? Man, it’s satisfying.
Whether you’re expanding your Cuban collection or looking for that special occasion smoke, the Sir Winston deserves a spot in your humidor. Just make sure you’ve got the time to do it justice. Clear your schedule, grab your favorite drink, and settle in. This is cigar smoking the way it was meant to be – unhurried, contemplative, and thoroughly enjoyable.
Ready to experience what makes this Churchill so special? Your humidor’s calling.
