Pairing whiskey and cigars can be tricky. For starters, whiskeys have a broad range of flavor profiles, from peaty or smoky, to sweet, to spicy, which can make finding the right cigar complicated. The next challenge is that both whiskey and cigars tend to be big and bold in flavor, which can easily become overpowering. Finally, there’s not a lot of reliable information out there about what constitutes a successful pairing – simply smoking a cigar with a glass of whiskey does not, contrary to popular belief, constitute a ‘pairing’.

Over the last decade, I’ve visited cigar shops and lounges across the country and in Nicaragua. Whenever I travel to visit a distillery, I always look into the local cigar shops. On occasion I’ll find shops that are well known to the distilleries – in one such instance a local shop had a retrofitted vintage airstream that it would bring out to the distillery every weekend. At a certain point I became curious about how to best pair whiskey and cigars, so I would ask wherever I went.

The result was somewhat shocking. No matter who I asked, it seemed that everyone had the same answer: if you smoke a full-bodied cigar, pair it with a full-bodied whiskey, and if you smoke a light-bodied cigar, pair it with a light-bodied whiskey. I heard that enough that I realized that most people were just repeating what they’d been told without really thinking critically about it.

Several years later I finally discovered what I believe to be the source of this information. I was interviewing someone from a cigar shop in Atlanta and I asked her how she made cigar recommendations to patrons. She said that she would ask them about their favorite beverage and if they liked black coffee or strong espresso, she would recommend a bold cigar, but if they liked sweeter drinks she would recommend something on the lighter side. It’s easy to see how this would get mistranslated into advice to pair bold with bold.

After I’d heard the same thing over and over, I was complaining to my friend Michael Veach. He told me I should just start writing about pairing whiskey and cigars. So I did. I’ve now been writing about and teaching my whiskey and cigar pairing methodology for eight years. What’s unique about it is that I am teaching folks how to find what they enjoy, rather than saying you will enjoy this cigar with this whiskey. All the recommendations I make for pairings come from this same process. 

The process begins with choosing a flight of whiskeys with varying flavor profiles. If I am using Kentucky bourbons, I will use Maker’s Mark, a wheated bourbon, Jim Beam Black, a traditional Kentucky bourbon, and Four Roses Yellow Label, a high-rye bourbon. If I am doing American whiskeys, I will use a bourbon, a rye, and an American single malt. You can choose whiskeys with different flavor profiles from the same distillery. I recently did a Heaven Hill flight that included Bernheim wheat whiskey, Larceny wheated bourbon, and Evan Williams bottled-in-bond bourbon for a more traditional Kentucky mash bill. 

There are a few key tips when creating a flight of whiskeys to pair with a cigar. First, start with a basic understanding of the flavor profile of the cigar. Bold, spicy cigars may tend to pair better with a sweeter wheated bourbon or a whiskey finished in a rum cask, so make your selections wisely. Second, don’t choose anything with an overly high proof. While whiskeys over 100 or 110 proof can pair well with cigars, that is advanced level. Choose whiskeys between 80 and 100 proof, at least for your first several flights. 

Then when it comes time to start smoking your cigar, take note of the predominant flavors. Take a sip of the whiskey and a puff of the cigar and take note of how those flavors interact. Then try the pairing the other way, starting with a puff of the cigar and then a sip of the whiskey to see how the cigar changes the whiskey. It’s all about picking out the nuances and looking for balance between the whiskey and cigar you are trying to enjoy together. 

Using this methodology in a group is often interesting because everyone will like something different. That’s kind of the point here – this methodology is designed to help you to identify what is most enjoyable to you, not to anyone else.  Be sure to take notes, and don’t be surprised if your favorite pairing changes as you smoke – cigars can change flavor dramatically with each third smoked. Most importantly, have fun. If you aren’t having fun pairing whiskey and cigars, you’re doing it wrong!    

Where To Smoke

The Louisville Thoroughbred Society

209 E Main St #200, 

Louisville, KY 40202

thelouisvillethorough
bredsociety.com

Louisville has a new indoor-ish cigar smoking facility for the first time in more than a decade. Following a total indoor smoking ban in 2008, even cigar lounges had to close their doors. Now, thanks to a few loopholes, there’s a new lounge in town. The Louisville Thoroughbred Society is members only, but memberships are very affordable if you are from out of town. There’s a large walk-in humidor that is serviced by local retailer Liquor Barn, and the selection is solid if mainstream. The smoking lounge appears to be completely enclosed, but upon further inspection it is actually 20 per cent open air, which satisfies the requirements for private smoking clubs in the city. There is comfortable club-style seating, including leather couches and chairs. It is climate controlled so smokers will always be quite comfortable. There is also a great bar on-premise, so those who enjoy a whiskey or cocktail with their cigars will be in luck. There are plans to bring a cigar expert in during busy times to help patrons select their perfect cigar and peruse cigar accessories. There’s plenty of room for big groups, but it’s also a nice place to relax and enjoy the view of the adjoining patio.

Where To Smoke

Red Phone Booth Atlanta

17 Andrew Young International Blvd NE

Atlanta, GA 30303

redphonebooth.com

Enjoy the Prohibition-themed speakeasy cocktail bar, complete with rare whiskeys and handcrafted cocktails alongside a curated collection of cigars. The cocktail menu includes classics such as the French 75, the Zombie, a Smoked Old Fashioned, and a Sazerac, but there are also more unique cocktails like a modified Whiskey Sour, an Elderflower Margarita, and even a riff on a Manhattan called the Never Say No. Memberships are available for those wishing to maintain a locker, but membership is not necessary to enjoy the space. Events include whiskey and food pairings, whiskey tastings, and more. The walk-in humidor includes Drew Estate, Camacho, Fuente, Cohiba, and others – more than 100 labels in all. Visitors can enjoy shooting a game of pool while enjoying cigars and cocktails, or dine in from a menu that includes small plates, Neapolitan pizza, and a rotating menu of house-made desserts. The atmosphere is formal – be advised there is a dress code that includes no ball caps or athletic clothing. Private events, including the rental of the pool table and a private kitchen, are available.