What to Drink with Cigars: 4 Cocktail Pairings That Will Make You Drool

Peanut butter and jelly. Steve McQueen and Mustang. Cigars and cocktails — what a terrible world it would be without classic pairings like these. (Or, really any of these legendary pairings.)

There’s something so beautiful about a perfect combination of sensations and flavors, especially if it’s a luxury cigar and a perfectly-crafted cocktail, hence our motivation for these five cigar and drink pairings, as suggested by Highclere Cigar CEO Adam von Gootkin and Cigar and Leisure expert Brian Ledtke. It’s time to puff and sip your way to bliss.

Romeo San Andres + Dark ‘n’ Stormy

cigar drink cocktail cuba librew dark and stormy
Elizabeth Fernandez/Getty Images

Another pairing designed to be an after-dinner treat, Ledtke suggests the newest offering from Romeo y Julieta: Romeo San Andres, a full-bodied, dark cigar with all the chocolatey, sweet, yet lightly spicy wonder of a chili-chocolate bar. “Pair it with something equally as dark,” Ledtke says, “with a bit of a kick. I’ve found that a Dark and Stormy made with the superb Barceló Imperial Onyx is just what this cigar needs. Surprisingly, opposites don’t always attract.”

Don’t know how to make and Dark and Stormy? We’ve got a simple recipe.

Macanudo Inspirado Red + Old Fashioned

whiskey old fashioned cocktail orange

Old meets new with Ledtke’s second suggestion, which merges the most classic bourbon whiskey cocktail known to man with a brand new cigar from the famed Macanudo line. Another spicy option, the Macanudo Inspirado Red uses aged tobaccos derived from volcanic soil and, “in order to help counteract a bit of the spice, it is best to pair with a bourbon or a thick stout,” Ledtke says. “I’ve found that an Old Fashioned made with Bulleit Bourbon Frontier Whiskey really complements the kick of the cigar, especially with its sweet and long finish.”

Top it off with everything you need to know about the Old Fashioned.

CAO Amazon Anaconda + Imperial Highball

highball cocktail japan

In the first duo to pop into Ledtke’s head, he calls out the CAO Amazon Anaconda, a cigar containing spicy Braganca leaf that perfectly compliments the spice and sweetness of a great rum (his go-to: Barceló Imperial). “Other prevalent notes are cocoa, earth, dried fruit, espresso, almond, and vanilla,” he says. “None of these flavors overshadow those of the Imperial Highball. You may want to pace yourself on the cocktail, though; this cigar has a slow burn and lasts well over two hours.”

Make it a double and learn more about the history of the highball.

Highclere Cigar + Gin and Tonic

gin vodka lime

Possessing both an approachable creaminess of the smoke and complexity reminiscent of dark, strong cigars, Highclere pairs well with a variety of cocktails, says von Gootkin. “Start your night with a nice glass of Dom Pérignon. The pistachio nuttiness and creamy draw of the Highclere allow the Champagne to express itself,” he says. “Similarly Sauterne, a very sweet dessert wine, after dinner with a Highclere is just heaven.”

Von Gootkin’s last cocktail pairing suggestion is a gin and tonic (which, come 2019, you’ll be able to make with a Highclere label gin inspired by the iconic English castle). “Something about the juniper, those citrus flavors, play really well. On the golf course, taking a break and having a cigar and cocktail, this is perfect. You’ve got that lime flavor and sparkle of the tonic that cleans your palate. It’s refreshing and great for summertime at the beach or glamping.”

The next round is on us: Here are the best gins for a gin and tonic.

Article originally published June 18, 2018.


10 Best History Books You Will Ever Read

We're featuring a three-part history of WWII as one book because an article about 10 books sounds much more neat and tidy. But you know what wasn't all that neat and tidy? Human history.

New Orleans Hotel Offers $15,000 Luxury Stay in Return for the Best Stolen Item

Sometimes crime does pay. All you need to do is be a man and own up to your crime.

How to Smoke a Cigar Like You Actually Know What You’re Doing

There are subtle conventions that cigar smokers tend to follow, and while you won't be ridiculed for not knowing them, nobody wants to look like a beginner.
Food & Drink

The Best Bottles of Whiskey You Can Buy For $20 or Less

We've listed good, cheap options for bourbon, Scotch, rye, Canadian, and Irish whiskies. You're welcome.