Cigar and Drink 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.

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.

Macanudo Inspirado Red + Old Fashioned
Old Fashioned

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.

Highclere Cigar + Gin and Tonic
best gins for gin and tonic

Possessing both an approachable creaminess of the smoke and a 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.

Romeo San Andres + Dark and Stormy
dark and stormy

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.

Partagas 1845 Extra Fuerte + Revel Stoke Root Beer-Flavored Whisky
cigar and drink pairings revel stoke root beer

Ready for a little something different? Ledtke swears by this root beer-flavored, smooth Canadian whiskey aged for four years in American oak barrels. “It’s absolute perfection served neat or on the rocks.” Pair that with a Partagas 1845 Extra Fuerte full-flavored cigar, which helps bring out the sweetness of the whiskey. “Whenever the vanilla scent of the whiskey mixes with the chocolate of the cigar you feel like you’re entrenched in a scrumptious dessert.”

If you’re planning a poker night, von Gootkin has some more tips for you.