When I started studying bourbon and cigar pairings with Michael Veach last spring, we already knew one thing: the conventional wisdom about pairing bourbon and cigars has got it all wrong. Everywhere you turn there are people telling you a full-bodied cigar needs a full-bodied bourbon and a light cigar needs a lighter-bodied bourbon. The problem with that is the full-bodied bourbon and cigar compete with each other for your attention and the light-bodied bourbon and cigar don’t have enough complexity. There has to be something opposite about each to complement each other.

What I didn’t expect is that proof would play such a huge role in the pairings. While I love a great barrel-proof bourbon as much as the next person, when you are looking for the flavor nuances brought out by a good bourbon and cigar pairing, high proof gets in the way. You could, of course, add a little water to proof it down. If you only drink Booker’s, try Booker’s with a hefty splash of water, preferably mixing water.

The learning curve is steep, but once you get the first few tastings under your belt you will be a pro. Now when I choose a cigar I have a pretty good idea of what bourbon will pair best with it. It’s not an exact science by any means, and the bottom line is go with what works for you. For this pairing I chose 3 bourbons that were all between 80 and 100 proof.

The Cigar

For this pairing I chose a Liga Undercrown Gran Toro gifted to me by a friend in celebration of my first publication on Cigar Aficianado.

This cigar has a Maduro wrapper and a medium body. There are notes of chocolate, leather, and spice in the smoke, which grows in complexity as it burns. This is around $10, making it a great cigar for the money.

Old Fitzgerald BiB 100 Proof

Nose– Stone fruit, brown sugar, baking spice

Palate– Stone fruit and leather

Together – The bourbon makes the smoke earthy with rich chocolate tones, while the cigar makes the bourbon taste like dark red cherry and baking spices. The combination is like a chocolate covered cherry pie.

Four Roses Yellow Label 80 Proof

Nose– Green apple and honey

Palate– Green apple and baking spice

Together– The bourbon mellows the smoke, bringing out honey and chocolate notes. The smoke brings the baking spices of the bourbon to the forefront. The combination tastes like apple pie a la mode.

Whiskey Row 88 Proof

Nose– Beautiful floral notes, brown sugar, and vanilla

Palate– Sweet corn and heavy baking spices

Together– The cigar dulls the sweetness of the bourbon and brings the baking spices to the forefront. The bourbon brings out the earthy notes in the cigar. They balance each other out very well.

The Verdict

Because I started with three bourbons I knew would work well together, I ended up with three enjoyable combinations. If I had to pick one I would say the Old Fitzgerald Bottled in Bond was my favorite combination, but again it’s hard to choose. Having a flight of bourbon with a cigar is totally legit if you don’t want to choose.


Photos Courtesy of Maggie Kimberl