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Cigars and Drinks: Perfect Match (Concierge Preferred)

Explore the perfect pairings for various types of cigars when it comes to wine, cognac, and more.

By Daniel B. Honigman

Picking the right cigar is like choosing a lover: Your tastes may change occasionally, but there’s always a time and place to enjoy the experience.

Well, maybe that’s a stretch.

Depending on the time of day—and your drink of the moment—certain stogies may tickle your fancy in a way others just can’t. But if you pair that Bud Light with a full-bodied maduro cigar, you may turn a few shades of purple if you have an empty stomach. And that green-colored, mild candela wrapper won’t stand a chance against many single malt scotches.

There’s good news: Everyone’s palate works differently, so it really doesn’t matter what you like. Good booze can turn an ordinary cigar into an extraordinary one, bringing out flavors nobody ever knew existed. But if you find the best pairing for that Macanudo Gold is a tumbler of your finest Mountain Dew on the rocks, go right ahead.

To help point you in the right direction, however, here are some pairings that you may enjoy:

With hints of espresso, chocolate—and a bit of spice later on—the Camacho Triple Maduro is a stogie that will sprout some hairs on your chest. It’s a very complex full-bodied smoke, so we wouldn’t recommend smoking it on an empty stomach. You may want to pair this one with a pint of Guinness Stout, but if that’s too much, go with an Anchor Porter.

The El Centurion Emperadores by Don Pepin Garcia is a medium-bodied cigar with a ton of flavor. It’s a bit hard to get a hold of—Don Pepin’s Tabacalera Cubana factory only made 50,000 of these babies—but if you can lay your hands on one, we guarantee you’ll enjoy it. Aged for three years, the Centurion is slightly leathery (sounds strange, but it’s a good thing), earthy and a touch spicy. It’s a nice treat with a glass of Mount Gay Extra Old Rum.

Once in a while, you really need to indulge. So why not go all out? The Martell Cordon Bleu (XO) is one of the finest cognacs commercially available, and the Ashton V.S.G. is one of the finest full-bodied cigars available. With hints of dark mocha, the Ashton is exceptionally smooth, but has the backbone to stand up to the aged cognac.

For the inner Chicagoan in all of us, there’s no greater honor than to have a drink with Da’ Coach. Or, in this case, have his drink. The Mike Ditka Cabernet Sauvignon (2004) is a surprisingly good, fairly inexpensive red. Pair it with the Los Blancos Criollo Selection for a true Windy City experience. (The Los Blancos office is based on Chicago’s North Side.) Morning smokers may enjoy the buttery Connecticut wrapper on the Rocky Patel Vintage 1999, paired with a mug of hot coffee from local chain Intelligentsia Coffee & Tea.

This story originally appeared as one of Concierge Preferred’s local guides.