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As an increasing number of Bourbon and whiskey events are featuring special cigar tastings or pairings, we wanted to provide a few tips on how to best taste a cigar with a whiskey.

Similar to tasting and pairing cuisine with whiskey, we’re looking for flavors that can complement, enhance or contrast. A combination of the three is also possible.

For the cigar, I wanted to pick a good classic smooth smoke like The Davidoff Nicaragua Pairing.  I headed to Holt’s Cigar Company where I purchase many cigars online.  (By the way, I ended up taking these Davidoff cigars and sharing them at the recent Kentucky Derby 144 –  see video below and on this link).


For the whiskey, I selected the Widow Jane Baby Jane Bourbon Whiskey from Brooklyn, New York. It’s youthful yet well-thought zest along with a creamy texture make one of our favorite craft Bourbon whiskeys.

This particular pairing allows the creamy and smooth nature of the cigar to be enhanced by the chocolate and candy corn flavors of the Bourbon whiskey.  The result is a candied and bolder experience of Davidoff Nicaragua which makes it taste even more like an “after dinner” within the smoke itself. More noticeable notes of cocoa, chocolate truffles, even hints of cappuccino are brought forward within the cigar as a result of the enhanced pairing.

Want to try this yourself?

Davidoff Nicaragua is available on this link. For the Bourbon, if you can’t find the Widow Jane Baby, I recommend a “corn forward” and sweeter Bourbon.

How to Taste a Cigar with a Whiskey


1. Much like cuisine, take a sip of the Bourbon or whiskey first. This is called “coating the palate” or “priming the palate.” The elements of the whiskey have to chemically get into your tongue, your mouth.

2. Take a draw of the cigar. It has to enter and greet your palate too.

3. Now the smoke and whiskey are combined and getting friendly with one another. Go back and forth and slowly and consciously be aware that each is coating your palette and continuing to build on the other for a flavor which will progress throughout the session.


4. Now ask yourself and discuss with your friends, what are the flavors doing?

Are they complementary? I.e. the same way mint and chocolate or peanut butter and chocolate would go together

Are they enhancing? Turning up both flavors on the volume scale for something new?

Or, are they contrasting? Do they fight each other? But if so, does the fight and conflict give birth to something either enjoyable?  Or do you need a new pairing?



Kentucky Derby 144 Video


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