Each cigar has unique flavor and characteristics that you should focus on when pairing with liquor. Start by focusing on your favorite cigars and your favorite types of liquor. As a basic rule, pair big bodied cigars with full bodies liquors, and lighter cigars with lighter choices, so neither overwhelms the other. After a bit of taste testing, you'll find a combo that works for each of your favorite cigars.
Brandy and Cognac
A glass of cognac and a cigar almost seems expected, but when paired poorly, the two can clash. Cognac is just one type of brandy, but by far the best known. Choose a VSOP (very special old pale) or XO (extra old), avoiding the younger VS varieties. A brandy that has aged longer presents more delicate flavor nuances. Cognacs tend to have a hint of vanilla and nuts, which can accent the same flavors in the cigar. You'll want a full-bodied cigar to avoid the strong alcohol scent from overwhelming the palate. Other types of brandy have fruitier or smokier flavors and can pair well with more delicate cigars. As the best traditional choice, a glass of brandy with your after-dinner cigar will almost always work.
Whiskey, Bourbon and Rye
Learning the difference between whiskey, bourbon and rye at this stage is less important than realizing that all three make great liquors to drink along with a cigar. These spirits offer a sweet, woody flavor that seems to make almost any cigar better. Just remember that rye tends to be spicier, which pair best with a mild cigar. As you select a drink, look for leather, nut and even butter with just a hint of sweet in both the liquor and the cigar. If you detect too much sweetness, with almost a syrupy aftertaste, the cigar will not gain much from the pairing. If you generally like American whiskey, then this pairing will serve you well.
With hundreds of scotches to choose from, in both the single malt and blended varieties, you will most likely find a challenge when pairing it with cigars. Start by finding a scotch you like, then taste other offerings from the same distillery. You'll find scotches with more honey and fruit will pair well with mild cigars, while those with more smokiness and nuttiness pair well with full-bodied cigars. Look to enhance the flavor of your scotch by choosing a cigar with similar qualities.
Rum tends to be made alongside cigars, which makes it a shoe-in for a perfect pairing. Most clear rums tend to be mainly used for mixing, while darker rums can stand alone for sipping. Your first challenge is to find a sipping rum, which should be smooth and sweet, without tasting like cough syrup. Then look for a cigar that has a natural creaminess to it with hints of vanilla. Spicier cigars tend to not pair as well with rum. If at a loss, pair cigars and rum from the same country or manufacturer.
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