The Ultimate Cigar Cocktail: ‘The Gentleman’s Flavor’

In 2018, I created The Gentleman’s Flavor as a website devoted to the interests of cigar lovers. The content to be found here was to encompass not only cigars, but also the many things that cigar lovers love to enjoy with them.

Things like cocktails.

Over the years, we’ve curated a wealth content geared toward heightening the experience of today’s cigar lover. This of course has come to include various pieces on cocktails, and more specifically – the pairing of cocktails with cigars.

Recently, this got me thinking, “the time has come to create the ultimate cocktail to be enjoyed with a cigar.”

Not something that just so happens to work well with a cigar, but rather something specifically crafted to serve as the perfect extension to a fine cigar; an optimal situation where a drink and a cigar can come together and marry as some sort of sublime unified whole.

I won’t bore you with details of the time-consuming processes that I took to finally establish this ultimate liquid companion to a cigar, but I will tell you this; at the outset, I felt that it had to be an old fashioned-style cocktail.

Something served over a large cube of ice in a double-old fashioned glass.

There’s just something special about holding a rocks glass and a lit cigar in the same hand, don’t you think?

Though the original lineup of ingredients make a wonderful team, if they all aren’t readily available in your locality, simply use your judgement and employ suitable substitutes.

Have some fun with it.

NOTE: The cigar is best held in your hand that holds the glass. Along with the torched orange zest, think of the cigar and the smoke that it exudes as a garnish.

Ingredient 1 – 100% Rye Whisky (Base Spirit)

I felt the need to center the cocktail around rye whisky.

Being in the midst of the biggest cocktail boom since pre-prohibition, rye has fallen into serious favour with cocktail creators. Rye typically embodies bold, spicy flavors that stand up well in mixed drinks, and can particularly stand up to the heat of a cigar.

The rye I ultimately landed on was Lot 40 Dark Oak 100% Rye.

World’s Best Whisky at the 2021 World Whisky Awards, it’s rested in #4 char barrels to create an unmistakably dark and bold character (we’ve also tried this with American straight rye, and our favorite is New Riff Kentucky Straight Rye).

Ingredient # 2 – Amaro (Bitter Element)

Amaro Averna is an herbaceous, bitter (Sicilian) Italian liqueur that always seems to jive particularly well with rye.

It is an excellent digestif, which means that though this cocktail can be enjoyed anytime, after a meal it will really hit the mark.

Averna displays complex notes of herbs, dried dark fruit, leather and spices. Like other amari (different varieties of amaro and meaning “bitter” in Italian), it has a ‘cola’ note, which hearkens to mind a rye and coke.

Ingredient #3 – Whisky Barrel-Aged Canadian Maple Syrup (Sweet Element)

I felt that the rich, smokey character to a whisky barrel-aged maple syrup adds the perfect amount of sweetness while remaining robust.

It creates more of a nice thick mouthfeel than basic simple syrup could ever dream of.

I was fortunate to have stumbled upon Giffin’s Whisky Barrel-Aged Canadian Grade A Maple Syrup. This dark grade syrup has been aged in freshly emptied Wolfhead Distillery whisky barrels for several months, which gives it smokey hints of charcoal, oak, and of course – whisky.

Ingredient # 4 – Tobacco Bitters (Bitter Element)

Flink’s Drinks Tobacco Bitters are meticulously crafted from locally grown Native American tobacco and a neutral spirit produced in southern Ontario. Two to three dashes contribute a bittersweet tobacco essence to the concoction. If Flink’s isn’t available, Fee Brothers’ Turkish Tobacco Bitters are easier to find and work great too.

Ingredient # 5 – Peated Single Malt Whisky or Smokey Mezcal (Supporting Spirit with an Element of Smoke)

To truly be a cocktail made to be paired with a cigar, it needed to have a pronounced element of smoke.

Knowing that some people aren’t lovers of peat, I’ve effectively made this cocktail to be enjoyed with either a smokey Islay Scotch whisky (I used Laphroig 10 here), or a mezcal with a smokey character if you wish to pass on the peat (I used Montelobos Espadin Mezcal here).

This liquid is to be added as a float on top of the finished cocktail prior to garnishing.

If you are a lover of peated whiskies, you can have a lot of fun by trying out countless different varieties, like Ardbeg or Lagavullin for example. To me, Laphroig 10 appears to be a bartenders peated whisky of choice, as it is used as a float in other cocktails, like the Penicillin.

It has elements of leather, wood and ash – all supported by an underlying heathered honey sweetness.

I continue to have a lot of fun in trying out different peated scotches and different smokey mezcals as the float on top of this drink and I encourage you to do the same.

The Cocktail: The Gentleman’s Flavor

‘The Gentleman’s Flavor’ was created as the ideal cocktail accompaniment to a cigar

Puff Puff Sip: Conclusion

As the creators of many of the world’s cocktails will tell you, arriving at the perfect combination of ingredients tends to take time and should not be rushed. I didn’t want to publish news of the ideal cigar-inspired cocktail until I was 100% certain that I that I had arrived upon a list of the best synergistic ingredients.

Thankfully, after testing out numerous formulas (and pairing them with different cigars), I am happy to say that I’ve devised what I believe to be is a cocktail that that is extremely complimentary to a cigar.

I have dubbed it “The Gentleman’s Flavor”, and hope that it can serve as an excellent accompaniment your cigar smoking experience.