Bourbon and Cigar Pairing FAQ

What is the best cigar to pair with bourbon?

It depends on what is in your glass, so start with the bottle. Here are two of our favorites for each kind of pour.

Smooth, lower-proof bourbon: the Perdomo Lot 23 Connecticut Toro brings creamy cedar and toasted almond, and the Ashton Churchill adds cream and a slightly sweet finish over a long, unhurried smoke. Both are mild, so they let a soft or wheated bourbon do the talking.

Everyday, mid-proof bourbon: the Arturo Fuente Double Chateau Maduro leans into dark chocolate, sweet spice and roasted nuts, a natural match for caramel and vanilla. The Padrón 1964 Anniversary Hermoso, Cigar Aficionado's No. 3 Cigar of 2020 (97), brings cocoa, toasted almond and leather in a cigar short enough for one good pour.

High-proof or barrel-strength bourbon: you need a cigar with weight. The My Father Le Bijou 1922 Grand Robusto answers with dark chocolate, espresso and black pepper, and the CAO Flathead V660 Carb, Cigar Aficionado's No. 3 Cigar of 2015 (95), adds a molasses sweetness that stands right up to the heat.

How do you pair a cigar with whiskey?

Match intensity first and flavor second. A rough guide by proof: under 90 proof, try a mild or mild-medium cigar. From 90 to 100 proof, go medium to medium-full. Over 100 proof or cask strength, choose a full-bodied cigar. Take a sip before your first draw and again every few puffs, and let each one reset your palate for the other. If you are new to this, there is no wrong answer. Start in the middle, notice what you like, and adjust from there.

Should you pair a cigar with bourbon, rye or Scotch?

All three work, and each leans a different way. Bourbon's caramel and vanilla sweetness suits cocoa-rich maduros. Rye's spice lines up with peppery Habano and Corojo cigars. A lighter, unpeated Scotch fits creamy, cedar-forward cigars, while a heavily peated Scotch needs a fuller cigar so the smoke doesn't overpower it.

What is the difference between a whiskey pairing cigar and a whiskey-infused cigar?

The cigars in this collection are traditional, non-infused tobacco chosen because they taste great next to whiskey. A whiskey-infused cigar has whiskey flavor added to the tobacco itself. If you want a touch of whisky character in the cigar, the Davidoff Winston Churchill Late Hour uses filler aged in Scotch whisky casks, and you can browse our flavored cigars for infused options.

Why do cigars and bourbon taste so good together?

Both get their character from slow aging. Charred oak barrels give bourbon its caramel, vanilla and toasted notes, and long fermentation and aging give premium tobacco its own sweetness, spice and toast. Those overlapping flavors are why a good pairing feels like the cigar and the glass are finishing each other's sentences.

How long should a cigar last with a pour?

Pick by the time you have. A Quick Smoke fits a single neat pour, a Power Hour cigar suits a relaxed hour with a second glass, and a Weekend Warrior is for the long night when the bottle stays on the table.