H. Upmann Sir Winston

Description

The Churchill That Made Churchill Famous

Look, I’ve smoked a lot of Churchills in my time – maybe too many if you ask my wife – but the H. Upmann Sir Winston is the one that reminds me why this vitola exists in the first place. Named after the man himself, Winston Churchill, this isn’t just some marketing gimmick slapped onto an oversized cigar. This is the real deal. The cigar that supposedly Sir Winston would have appreciated, though between you and me, I think he’d smoke just about anything as long as it was Cuban.

Here’s the thing – when Habanos S.A. decided to honor Churchill with this particular vitola in the H. Upmann line, they weren’t messing around. They chose one of Cuba’s oldest and most respected brands, dating back to 1844, and gave it a format that demands your attention and your time. We’re talking about a serious smoking experience here, not something you light up during a quick break. This is a celebration cigar. An occasion cigar. The kind you pull out when you’ve got two solid hours and nowhere else to be.

What Makes the Sir Winston Special (And Why I Keep Coming Back)

H. Upmann has always been that brand that doesn’t scream for attention. It’s not Cohiba with its premium pricing and fancy bands. It’s not Montecristo with universal name recognition. No, H. Upmann sits quietly in the corner of your humidor, being consistently excellent without making a fuss about it. The brand has this reputation – deserved, I might add – for producing mild to medium-bodied cigars with remarkable elegance and complexity.

The Sir Winston takes everything that makes H. Upmann great and stretches it out over a luxurious 7-inch format. It’s like taking a beautiful melody and letting it play for longer – you get to appreciate every note, every nuance. And the wrapper – oh man, the wrapper on these things when they’re properly aged – it’s got this silky, oily quality that just looks right. That golden-brown Vuelta Abajo leaf with maybe a few veins here and there, because we’re talking about hand-rolled Cuban cigars, not plastic perfection.

This cigar is for the smoker who appreciates subtlety. If you’re the type who needs your cigar to punch you in the face with pepper and strength, this probably isn’t your speed. But if you’re someone who can sit back and pick out delicate flavor transitions, who doesn’t need bold to mean good, then you’re going to love this. I genuinely don’t understand why more people don’t talk about the Sir Winston when discussing great Churchills. It gets overshadowed by the Montecristo No. 1 and Romeo y Julieta Churchill, but it holds its own against both.

The Smoke: From First Light to Final Puff

Okay, so let me walk you through what actually happens when you light one of these up. And I’m not gonna lie – the first time I smoked a Sir Winston, I had different expectations. I thought it was going to be bolder, more in-your-face. I was wrong, and I’ve never been happier to be wrong about a cigar.

The cold draw gives you this gentle preview of what’s coming. There’s cedar right away – that classic H. Upmann cedar note that reminds me of walking into a proper tobacconist’s shop. Maybe a hint of hay or dried grass. Nothing aggressive. Nothing sharp. Just welcoming and familiar. The construction on these is typically excellent, though I’ve had the occasional one that needed a little touchup. That’s Cuban cigars for you. Hand-rolled means variation, and honestly, I wouldn’t want it any other way.

First third – and this is where the Sir Winston starts showing its class – you get this creamy smoke texture that just coats your palate. It’s smooth, almost buttery. The flavor profile leans into cedar and light coffee notes, not espresso, more like a café con leche. There’s this subtle sweetness underneath everything, kind of like honey or light caramel. The pepper is there if you look for it on the retrohale, but it’s playing backup, not lead guitar. The burn line stays pretty even if you’re not puffing too fast, and the ash holds firm for a good inch or more. That light gray ash with clean lines – that’s telling you the tobacco is quality stuff.

Thing is, the second third is where this cigar really earns its reputation. The complexity starts building. You’re still getting that cedar foundation, but now there’s more going on. I pick up toast notes, maybe some roasted nuts – almonds or hazelnuts. The coffee deepens just a touch. And here’s what gets me – there’s this floral quality that comes and goes. It’s subtle, not like you’re smoking a bouquet, but it’s there, adding this layer of sophistication. The strength nudges up slightly into solid medium territory, but it never gets aggressive. The smoke production is generous without being overwhelming. Perfect, really.

Final third – and I know this sounds dramatic, but this is where I decide if a cigar was worth the time investment – the Sir Winston typically doesn’t disappoint. Some Churchills get harsh or bitter in the last stretch. Not this one. It maintains that creamy character while introducing just a bit more earthiness, maybe some leather. The pepper picks up on the retrohale, giving you that little kick that reminds you you’re smoking a Cuban. The sweetness fades but doesn’t disappear completely. And if you’ve been patient with your puffing, you can smoke it down pretty far without any heat or harshness. That’s craftsmanship.

How It Stacks Up Against the Competition

Real talk: the Montecristo No. 1 gets more attention, and I get it – it’s a bit more assertive, has that classic Montecristo punch. But the Sir Winston is more elegant. It’s less about making a statement and more about having a conversation. The Romeo y Julieta Churchill is probably the closest comparison in terms of strength and profile, but I find the H. Upmann to be more consistent and slightly more complex. The RyJ can be great, but it can also be just okay. The Sir Winston is rarely just okay.

What to Drink With It (And When to Smoke It)

Look, you can smoke this with whatever you want – I’m not your mother – but I’ve found some pairings that really work. A good aged rum is my go-to. Something like a Havana Club 15 year or a Diplomatico Reserva Exclusiva. The rum’s sweetness complements that honey note in the cigar without overwhelming the subtler flavors. Cognac works beautifully too, especially something in the VSOP range. Not too young and harsh, not so old and complex that it fights with the cigar.

Coffee and the Sir Winston? Absolutely. A smooth, medium roast – nothing too dark or bitter. The coffee and tobacco play off each other in this really pleasant way. I’ve also had this with champagne during a celebration, and honestly, it was fantastic. The dryness and effervescence cleansed the palate between puffs, letting you experience the flavors fresh each time.

As for when to smoke it – this is a late afternoon or early evening cigar for me. It’s too long and requires too much attention for a morning smoke, unless you’ve got nothing else to do that day. It’s perfect for a lazy Saturday afternoon on the patio, or after a good dinner when you’ve got time to let your food settle and your day wind down. Special occasions? Absolutely. But here’s the thing – don’t wait for permission to enjoy these. Life’s too short to save all your good cigars for “someday.”

Aging and Storage Considerations

Okay, so here’s where I might lose some of you, but hear me out: the Sir Winston benefits significantly from aging. Fresh from the factory, it’s good. But give it two or three years in your humidor at proper conditions – around 65-68% humidity and 65-70°F – and it transforms. That cedar becomes more refined. The creaminess intensifies. The rough edges, if there were any, completely smooth out.

I’ve got a box from 2015 that I’m still working through, and those cigars are smoking like a dream right now. The flavors have melded and married in a way that just doesn’t happen with young tobacco. That’s the beauty of Cuban cigars and long filler tobacco – they’re alive in a way, still developing even after they’re rolled. Between you and me, if you can afford to buy a box and forget about it for a few years, that’s the move. I know that’s not always realistic, but even six months of rest can make a noticeable difference.

Storage-wise, these are forgiving but not indestructible. Keep them away from temperature swings. Don’t store them with super strong cigars unless you want flavor contamination – though honestly, H. Upmanns have a fairly distinct cedar character that holds its own. I keep mine in a separate compartment in my tower humidor, alongside other mild to medium Habanos. They play well with others in that strength range.

A Word on Vintage and Limited Editions

Now, the standard production Sir Winston is what we’ve been talking about, and it’s excellent. But H. Upmann occasionally releases vintage editions or special releases that include this vitola. If you ever come across aged stock or vintage boxes – I’m talking pre-2010 especially – and they’ve been stored properly, grab them. The quality of Cuban tobacco from that era, particularly the wrapper leaves, was exceptional.

I smoked a Sir Winston from a 2008 box last year, and I’m not exaggerating when I say it was one of the best Churchills I’ve ever had. The aging had taken everything good about the cigar and amplified it while smoothing out any minor inconsistencies. Was it better than a fresh one? Absolutely. Was it worth the wait? Without question. Thing is, you need patience for this game, and not everyone has it. I get it. But if you do, the Sir Winston rewards patience like few other cigars.

Construction and Quality Control

Let me be honest with you about Cuban quality control – it’s gotten better over the years, but it’s still not perfect. I’ve had Sir Winstons with flawless construction and burn, and I’ve had ones that needed multiple touch-ups. That’s part of the deal with Cuban cigars. They’re hand-rolled by human beings having human days. Some rollers are better than others. Some days the tobacco is more cooperative.

That said, the Sir Winston typically shows good construction. The draw is usually somewhere between slightly firm and perfect – I prefer a little resistance anyway. The cap is cleanly applied, rarely any wrapper issues. The bunch and fill are consistent enough that you’re not dealing with tunneling or constant burn problems. When you do get a perfect one – and most of them are pretty close – it’s a reminder of why Cuban cigars still hold the reputation they do.

The wrapper on these deserves its own mention. Vuelta Abajo leaf, when it’s good, has this particular quality – slightly oily, supple, not too veiny. The Sir Winston usually features very nice wrapper leaves. Not always flawless, but always quality. And that matters because the wrapper contributes significantly to the overall flavor, especially in a mild to medium cigar like this.

Final Thoughts From the Lounge

So here’s where we land with the H. Upmann Sir Winston – it’s a cigar that doesn’t demand your attention but absolutely deserves it. In a world of bold, aggressive, full-bodied smokes competing for shelf space, the Sir Winston takes a different approach. It’s refined, elegant, and unapologetically subtle. And you know what? That’s exactly what makes it special.

This isn’t the cigar you pull out to impress someone who doesn’t know cigars. They’ll probably find it too mild, too long, too whatever. This is the cigar you smoke when you’ve developed your palate enough to appreciate what’s NOT there as much as what is. No harshness. No bitterness. No overwhelming strength that masks everything else. Just clean, refined Cuban tobacco expressing itself the way it should.

If you’re looking to explore what H. Upmann does best, or if you want a Churchill that you can smoke without needing a nap afterward, the Sir Winston is calling your name. Give it proper storage, give it some age if you can, and give it your time and attention when you light it up. It’ll reward you for all three.

Now, if you’ll excuse me, I’ve got one waiting for me in the humidor that’s been aging since 2018. Been saving it for no particular reason other than the fact that patience makes it better – and today seems like as good a day as any to stop waiting. That’s the thing about these cigars – they remind you that sometimes the best moment is right now.