How to Pair Whisky and Cigars.

Generally speaking, when Pairing a spirit with cigars you want to stick to the brown or darker spirits like whisky, rum, cognac and brandy.  The cardinal rule when pairing spirits with cigars is that you should always match the body of the smoke with the body of the drink.  A full-bodied cigar tends to pair best with a full-bodied whisky.  Milder cigars often perform well is lighter whiskies.  An imbalance in one flavour profile can drown out the other or worse, a milder spirit might find the off-notes in a fuller cigar.  This rule will ensure that you will avoid mistakes more than discover great unions.  Despite this logic occasionally some sublime pairings will lead you to discover opposites attract.

The important thing to remember when pairing anything with whisky is that you want to try to focus on complementing the flavours.  This being said, when starting with a pairing think of the flavours of vanilla, maple syrup, honey, caramel, nuts, charred wood and dried fruit.  These notes will often go well with many cigars.  This is due to the way they pair with the flavours of leather, dark toast, peppery tobacco,

and earthiness of the cigar. 

So which Whisky with what Cigar?

Bourbon tends to work well with a large amount of cigars as the structure of the bourbon provides the sweet and woody notes that will compliment a large number of stronger cigars.

Canadian Whisky tends to work well with milder cigars as it is very smooth and will not over power the cigars notes.  Notes of vanilla from the whisky will work well with the tone of the cigar.  Some of the higher rye whiskies can work with stronger cigars.

Irish Whiskey tends to work similar to the way Canadian Whisky pairs with cigars but can also pair very well with cigars that have a bit more of a fruitier side.  I would also recommend testing Irish Whiskey with medium to strong cigars simply because of how well Irish Whiskey works with coffee. 

Scotch Whisky is a little bit more fickle as different regions have different flavour profiles.  I recommend working with a few options to find the right balance when it comes to Scotch and Cigars as there is a larger gambit of flavours with the Strong cigars and smokiness of Islay Scotches to the lighter fruitier cigars with a smooth Lowland Scotch. 

Sources:

https://www.whiskyadvocate.com/pair-whisky-cigars/#:~:text=The%20cardinal%20rule%20is%20that,perform%20well%20with%20lighter%20whiskies.

https://www.cigaraficionado.com/cigar101