H. Upmann Gran Reserva Sir Winston 2011

Description

I hadn’t touched a cigar in nearly three years. It wasn’t a health kick, exactly, and it wasn’t some grand moral stand—I just woke up one Tuesday in 2021 and decided I’d had enough of the ash and the lingering scent of cedar on my jackets. I put the cutters in a drawer, gave my humidors to my brother, and walked away. But life has a funny way of circling back on you. Last week, I found myself back in my father’s old study. You know the kind of room—heavy mahogany desk, floor-to-ceiling bookshelves filled with titles nobody’s read since the seventies, and that thick, permanent smell of old leather and pipe tobacco that seems to seep into your pores the moment you cross the threshold.

I was there to clear out some files, but the air in that room did something to me. I felt this strange, twitchy energy. My heart was racing, not from stress, but from a sudden, sharp realization that I was done with my hiatus. I didn’t want a cigarette, and I didn’t want a drink. I wanted a moment of quiet reflection that only a long, slow-burning stick can provide. I reached into the back of his desk drawer—the “secret” one he thought I didn’t know about—and my fingers brushed against a sleek, black lacquered box. I pulled it out, and the gold lettering caught the light of the green banker’s lamp. It was a box I’d gifted him years ago and he’d never touched. A time capsule from 2011.

That smoke? The H. Upmann Sir Winston Gran Reserva Cosecha 2011. I figured if I was going to break a three-year fast, I might as well do it with something that had been waiting for me as long as I’d been away.

The Specs

Construction: A Five-Year Nap

I gotta say, holding a Churchill after three years of empty hands feels significant. It’s a lot of cigar. This isn’t one of those quick lunch-break smokes; this is a commitment. The wrapper on this Gran Reserva is something else. It’s got that classic Cuban sheen—not oily like a Broadleaf, but more of a matte, silky texture that feels like expensive stationery under your thumb. Because this tobacco was harvested in 2011 and aged for a minimum of five years before it even saw a rolling table, the leaves have this settled, relaxed look to them. No aggressive veins, no soft spots. Just a solid, uniform roll.

I clipped the cap with an old double-guillotine I found in a pencil cup. The pre-light draw was exactly what I remember H. Upmann being: open, but with just enough resistance to let you know it’s there. I caught notes of cold hay and a bit of that “barnyard” funk that tells you the fermentation was handled right. It felt heavy in the hand, balanced. I sat back in my dad’s leather chair, the springs creaking under me, and toasted the foot. I wasn’t rushing. When you’ve waited three years, another thirty seconds of toasting doesn’t hurt.

The First Third: The Awakening

The first few puffs were like seeing an old friend who hasn’t changed a bit. The smoke output was generous. Right out of the gate, I got this hit of sweet orange peel. It wasn’t acidic, though—more like a dried zest you’d find in a high-end chocolate bar. Speaking of chocolate, there’s a creamy milk chocolate vibe that sits right on the tip of the tongue. It’s smooth. Real smooth. I think that five-year aging process really rounds off the sharp edges you sometimes get with younger Cubans.

About an inch in, a bit of cinnamon started dancing around the edges. It’s a “warm” smoke, if that makes sense. It’s not spicy like a Nicaraguan pepper-bomb; it’s more of a kitchen spice cabinet warmth. I also noticed a distinct cedar note, which might have been the cigar or might have been the fact that I was sitting in a room literally lined with wood. Either way, the earthiness started to ground the sweetness. It’s a medium-strength start, which was perfect for my “un-virgin” lungs. I didn’t want to get knocked out; I wanted to be eased back into the lifestyle. The burn was straight as a razor, which is always a relief when you’re dealing with a stick this long.

The Second Third: The Complexity Deepens

As I moved into the middle of this seven-inch journey, the profile shifted in a way that honestly surprised me. You ever have one of those moments where a flavor just clicks? For me, it was peanut butter. I know, sounds weird for a cigar, but it was there—this fatty, nutty richness that coated the palate. But it wasn’t alone. There was this sharp, cranberry-like tartness that cut right through the fat. It’s a brilliant contrast. One second you’re tasting creamy nuts, the next you’ve got this zingy fruitiness.

The “baker’s spices” started to ramp up here. Nutmeg and maybe a little bit of clove. The milk chocolate from the first third evolved into more of an espresso bean bitterness, but it stayed in the background, acting like a foundation for everything else. The hay note was still there, but it felt more like “sweet hay” now, like a field in the sun. I gotta tell you, the complexity was solid. Every few puffs, I felt like I was picking up something different. It’s a nuanced experience. It doesn’t scream at you; it whispers. You have to pay attention, which was exactly what I wanted while I sat there in the quiet of the study.

The Final Third: The Grand Finale

By the time I hit the final two inches, I was feeling that energetic buzz I’d started the day with, but mellowed out by the nicotine. The strength stayed firmly in the medium camp, never crossing over into that “I need to lie down” territory. The retrohale—which I usually avoid because I’m a wimp—was surprisingly pleasant. It was pure caramel candy sweetness. I’m talking thick, sugary, melt-in-your-mouth caramel. It was the highlight of the whole smoke for me.

There was a bit of white pepper that showed up toward the end, just to remind me it was a cigar. The construction held up mostly well, though I did have to reach for my lighter once or twice to touch up the burn line. Nothing major, just the usual Churchill maintenance. The heat stayed low even as I got down to the nub. I didn’t want to put it down. I stayed in that chair until my fingers were practically touching the cherry, soaking in the last of that leather and earth profile that had become the backbone of the finish.

Pairing Recommendations

Since I was in my dad’s study and feeling a bit nostalgic, I didn’t go for anything fancy. But if I were to do this again, here’s how I’d play it:

• Aged Rum: Something like a Diplomatico Reserva. The sweetness of the rum would play off that orange peel and caramel beautifully.
• Black Coffee: A medium roast with some citrus notes. You don’t want a dark roast that’s going to overpower the nuanced cranberry and peanut butter notes of the cigar.
• Vintage Port: If you really want to lean into the “Gran Reserva” vibe, a nice tawny port would be a killer companion for the final third’s caramel sweetness.

The Verdict

Was it worth coming out of retirement for? Absolutely. The H. Upmann Sir Winston Gran Reserva Cosecha 2011 isn’t just a cigar; it’s a slow-motion film. It takes its time to tell a story. It’s not for the guy who wants a quick hit of Vitamin N while he mows the lawn. This is for when you have two hours, a quiet room, and a lot on your mind.

The flavor transitions are distinct without being jarring. The aging of the 2010 crop tobacco has clearly done its job, smoothing out the rough edges and leaving behind a sophisticated, layered profile. It’s a medium-bodied masterpiece that respects the smoker. It’s not cheap—at $100 a pop (if you can even find them at that price anymore)—but for a “first smoke back” or a milestone celebration, it’s a solid choice. I left that study feeling refreshed, smelling like cedar and caramel, and knowing that my “retirement” was officially over. I think I’ll go buy a new humidor tomorrow.

Final Thought: If you find a box of these, don’t let them sit forever. They are in a prime smoking window right now. Light ’em up.