Italians on Italians
Beyond Toscano
Il Sigaro della Sera
It’s an iconic image, the picture of a smart-suited gentleman relaxing in his favorite chair with a fine cigar and a class of liquor. But while there’s no denying the elegant impression, not all liquors works well with cigars.

The classic pairing is often whisky, or cognac on the rocks. Like cigars, good whisky and cognac has a rich, elegant range of flavors and taste notes, that when paired with pleasures of similar complexity, are only enhanced. 
Darker, complex spirits and liquors work best with cigars, especially a single malt whisky, bourbon or rum, where the smooth, malty tastes offer a warming companion whose flavors can hold their own against a cigar. By contrast, white liquors like vodka, gin or tequila tend to become easily overwhelmed by the complexities of a cigar. 

Even if you stick to dark liquors with your pairing, there are a few things to watch out for. Whiskies with a smoky finish can seem to lose their flavor, as the cigar smoke will confuse the taste-buds. So if you enjoy stronger cigars, pair them with rich liquors, so as not to overpower and pick a malt with hints of vanilla or oak if you’re after a lingering finish.