The H Upmann No.2 Isn’t What Most People Think It Is
Here’s the thing that drives me absolutely nuts – everyone and their brother thinks the H Upmann Number 2 is some kind of beginner’s Cuban. “Oh, it’s mild,” they say. “Perfect starter cigar.” Bull. I’ve been smoking Cubans for over two decades now, and let me tell you something: whoever’s spreading that rumor clearly hasn’t spent quality time with this torpedo.
I remember my first No.2 back in ’03. Buddy of mine brought a box back from his honeymoon in Cancún (yeah, I know, probably fakes, but they weren’t). We’re sitting on his deck in August – humid as hell in Georgia – and I’m expecting this gentle, docile smoke. Twenty minutes in, this thing’s throwing leather and earth at me like it’s got something to prove.
That was my introduction to what I now consider one of the most underestimated cigars in the H Upmann lineup.
First Impressions: Don’t Judge This Book
The H Upmann No.2 comes at you looking pretty traditional – that classic torpedo shape (they call it a belicoso, but let’s be honest, it’s basically a torpedo). Medium brown wrapper that’s usually got a bit of tooth to it. Nothing flashy. The band’s got that understated elegance H Upmann’s known for since… Christ, since before my grandfather was born.
But here’s where it gets interesting. The pre-light draw? You’re getting hints of what’s coming, but it’s playing coy. Little bit of cedar, maybe some hay. Sometimes there’s this faint sweetness that reminds me of dried fruit. But don’t let it fool you – this cigar’s got layers.
Construction’s usually pretty solid. I’ve probably smoked… hell, must be close to 200 of these over the years, and I can count the problematic ones on one hand. The torpedo head lights evenly if you’re patient with it (and you better be patient, or you’ll scorch the wrapper and hate yourself for it).
The Smoke: A Journey That Actually Surprises
Okay, so here’s where I’m gonna get a bit controversial. Everyone talks about cigars in thirds – first third this, middle third that. Honestly? That’s not how I experience the H Upmann Number 2. This cigar flows more like a conversation than a textbook.
It starts conversational – that cedar I mentioned comes through stronger, joined by this clean tobacco flavor that’s distinctly Cuban. Not harsh, but definitely present. There’s a creaminess too, which is probably where people get the “mild” idea from. But stick with it.
About an inch in (and this varies depending on how you’re smoking it, what the humidity’s like, whether you’re drinking something with it), the H Upmann No.2 starts showing its real personality. The earth I mentioned earlier? It’s not just earth – it’s like rich potting soil after a spring rain. Sounds weird, but trust me on this.
Then – and this is why I love this cigar – it throws you a curveball. Somewhere around the halfway point, you’re gonna get hit with spice. Not pepper exactly, more like… you know when you’re cooking and you add just a touch of white pepper to cream sauce? It’s subtle but it changes everything.
The back half is where the H Upmann No.2 earns its keep. Leather comes in strong, but it’s not overpowering. There’s still that underlying creaminess, but now it’s playing backup to some serious complexity. I’ve tasted everything from coffee (not espresso, more like a medium roast) to what I swear is a hint of orange zest. My buddy Marcus thinks I’m crazy with the orange thing, but I stand by it.
What I Drink With It (And What Actually Works)
Look, I’ve tried everything with this cigar. Everything. And here’s what actually works, not what some sommelier tells you should work.
Coffee? Absolutely. But skip the fancy stuff. I’m talking about a good, honest cup of Folgers or Maxwell House. Something with enough body to stand up to that leather and earth, but not so complex it’s fighting for attention. I’ve had some of my best H Upmann No.2 experiences on Sunday mornings with black coffee and the newspaper.
Bourbon works if you’re doing it right. None of this top-shelf nonsense – save your Pappy Van Winkle for a Cohiba. Maker’s Mark, neat, maybe a single ice cube if it’s summer. The sweetness plays beautifully with that creamy texture, and the bourbon spice complements rather than competes.
But here’s my secret weapon (and I can’t believe I’m sharing this): A good amber ale. Specifically, Samuel Adams Boston Ale. I know it sounds weird, but the maltiness bridges perfectly with the tobacco, and there’s enough hops to cleanse your palate between draws. Discovered this combination completely by accident at a poker game in ’08 and haven’t looked back.
Wine people are gonna hate me for this, but most wines don’t work. Too acidic, fights with the tobacco. If you absolutely must do wine, try a Malbec. Something with enough tannins to hold its own.
Who Should Smoke This (And Who Shouldn’t)
Here’s where I’m gonna ruffle some feathers. The H Upmann No.2 isn’t a beginner cigar. I don’t care what the guy at your local shop told you. Yeah, it starts mild, but if you can’t appreciate complexity, you’re missing the point.
This is perfect for someone who’s smoked maybe 50-100 cigars and is ready to understand what Cuban tobacco can really do. It’s educational without being punishing. You can learn from this cigar.
Experienced smokers who think they know everything? This might surprise you. I’ve handed these to guys who only smoke Padróns or Fuente Opus X, and watched them get humbled. Cuban tobacco has its own language, and the H Upmann No.2 speaks it fluently.
Who should skip it? Honestly, if you’re looking for a quick smoke, pass. This demands at least an hour of your time, probably closer to 90 minutes if you’re doing it right. Also, if you only like full-bodied cigars, this might feel underwhelming at first. (Though I’d argue you should smoke it anyway – might teach you something about subtlety.)
And for God’s sake, don’t buy this if you’re gonna smoke it right away. Which brings me to…
Storage and the Patience Game
Cuban cigars need time. The H Upmann Number 2 especially. I’ve smoked these fresh from the shop (don’t judge me, sometimes you can’t wait), and they’re… fine. But give them six months in your humidor at 65% humidity, and they transform completely.
That harshness some people complain about? That’s young tobacco talking. Time smooths it out, lets those flavors marry properly. I’ve got a box from 2019 that I’m still working through, and every one has been absolutely spectacular.
Temperature matters too. I keep mine at about 68°F. Any warmer and they smoke too fast, any cooler and they don’t develop properly. And rotate your stock – don’t be that guy with a 20-year-old box that’s all dried out because you forgot about it.
One weird thing I’ve noticed: these cigars seem to respond well to seasonal changes. I swear the ones I smoke in fall taste different (better, actually) than the summer ones. Could be psychological, but I don’t think so.
The Controversial Take
Alright, here’s where I’m probably gonna get some hate mail. I think the H Upmann No.2 is better than the Montecristo No.2. There, I said it.
Everyone goes crazy for the Monte, and don’t get me wrong, it’s a great cigar. But it’s gotten predictable. The H Upmann No.2 has more personality, more willingness to surprise you. The Monte is like dating someone beautiful but boring. The H Upmann is like dating someone interesting who happens to also be beautiful.
Plus, the H Upmann Number 2 doesn’t come with all the pretension. You can smoke this cigar without feeling like you need to pose for Instagram.
Quick Answers to Questions I Get All the Time
How long does it take to smoke?
Plan for 75-90 minutes. Don’t rush it – this isn’t a cigar you puff on while checking your phone.
Are the fakes that common?
Unfortunately, yeah. Stick to reputable dealers. If a deal seems too good to be true, it probably is. I’ve been burned before (literally – fake Cubans burn terribly).
Should I age them?
Absolutely. Minimum six months, but a year is even better. Your patience will be rewarded.
What’s the strength level really?
Medium, leaning toward medium-full in the back half. Don’t smoke this on an empty stomach unless you’re experienced.
Bottom Line
The H Upmann No.2 is what got me seriously interested in Cuban cigars, and after 20+ years, I still reach for them regularly. They’re not flashy, they don’t try to impress you with overwhelming strength or exotic flavors. They just deliver a consistently excellent smoking experience that rewards attention and patience.
These reward you if you’re ready to appreciate what they offer. Just don’t expect them to be mild, don’t smoke them too fast, and for the love of all that’s holy, let them rest in your humidor for a while before you light one up.
This is a cigar that’ll teach you something about tobacco, about Cuban craftsmanship, and maybe about yourself if you let it. That’s worth more than I can put into words in my book.
Explore more
Browse all H. Upmann cigars, see our H. Upmann price guide, or try the H. Upmann Magnum 56 EDICION LIMITADA 2015 and H Upmann Magnum 50s. Store yours in a seasoned humidor and see our guide on how long cigars last. Learn more from Wikipedia, the official Habanos S.A. site.
