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Pairing Drinks With Cigars
While the exact history is unknown, the origins of the modern cigar can be traced back thousands of years. Ever since those tobacco leaves were rolled to create the first primitive cigar, the fascination has spread all over the world. A cigar can tell a story; from the shape and shade of the wrapper to the specific ageing, drying, and infusing, each make is unique in its own right.
Because of the variety of flavors that are available to a smoker, it should be no surprise that some specific makes work better with certain alcoholic beverages more than others. A carelessly thrown together combination of booze and tobacco can result in the worsening of both flavors; contrastingly, an artfully constructed pairing of drinks and cigars can smartly compliment one another for a wondrous taste. While there may be some trial-and-error involved when finding the right combination for your own personal preference, below are some guidelines to help you.

Cognac is the traditional, almost clichéd, drink to have with cigars. This is largely because of timing – both were usually taken after meals, and so they naturally became linked. Arguably, there is no better drink to combine with a cigar after a meal.

When buying cognac, pay attention to the age designation of the bottle. VS (Very Special) is the lowest category of age, and should generally be ignored for pairing with cigars. The middle age bracket is designated VSOP (Very Special Old Pale), and indicates ageing of at least four and a half years. Mild and medium-bodied cigars go particularly well with this age of cognac.

Ah, scotch, the characteristic “ying” to a cigar’s “yang” . . . a skillful pairing of this spirit with the right cigar can be a life changing experience. The smoky quality of a fine single malt, derived from the smoked peat used to filter the spirit, marries perfectly with a good cigar. Carefully aged in oak barrels to achieve a smoky flavor, this particular whisky seems predestined to be intertwined with a fine stick. However, be warned that scotch is not for everyone; packing a powerful punch of flavor, this masculine drink often needs to be approached slowly and may take time to develop an affinity for. With this in mind, if you aren’t fond of this spirit, perhaps reserve your cigars for a different beverage. However, if you have developed a refined palette for this expensive whisky, than a whole wide world of cigar possibilities await you. As holds true for all alcoholic beverages, the more mild or watered down the drink is, the wider the cigar should be in order to couple with the lightness of flavors.

In the world of spirits, small batch and single barrel Bourbons are super premium products that have the complexity and depth of flavor to stand up to a cigar. The small batch Bourbons are bottled at a higher proof level, which gives them a backbone of strong flavors, and they marry well with medium- and full-bodied cigars.

Rum and cigars both hail from the Caribbean, so it’s no coincidence that they work well with one another. Match the spiced and sweet molasses undertones of this full-bodied dark spirit with a creamy cigar. There are clear rums as well but, in all honesty, most combinations with this spirit will be subpar. Rum in its cheapest and most basic form can ruin even the best cigar, accentuating any roughness of the smoke until all pleasure is lost completely. However, if you buy carefully, the right rum can be a perfect complement to a good cigar.

When pairing a cigar with wine, the most commonly made mistake is overpowering the taste of a light wine with a darker cigar, and this is especially true if you’re a fan of white. Generally speaking, white wine is best accompanied by a mild cigar. However, this is perhaps the most difficult drink to find an ideal smoking match for; if you’re looking to have a successful pairing of crushed grapes with cigars, look to red wine.
Like tobaccos and wrappers, red wines can cover a wide spectrum that ranges from earthy to sweet. Naturally, you’ll want to find a cigar that harmonizes. Take into account whether the particular drink is medium or full-bodied and strive to find a cigar that will match the wine’s robust taste without it being overwhelming or masked. 

While it would be disappointing to pair a quality cigar with a classic American Adjunct Lager (ie Budweiser, Miller, Coors, et al), but the marriage of a superb craft beer with the right tobacco can make for one amazing night. As with wines, it all comes down to corresponding the flavors and subtleties with your chosen stick. Because wheat beer tends to be smoother and fruity, opt for a lighter smoke. For a stout (such as the classic Guinness) you may want to pair it with a darker cigar. You may be surprised to find that more bitter hops can keep up with even the full-bodied cigars your humidor might be holding,

Other Spirits
As with any complementary coupling, it is crucial neither item overpowers the other too strongly. Because most cigars have robust flavors (even the mild ones) it is generally best to stick with the darker spirits when pairing with a cigar. Clear or lighter colored spirits such as vodka or gin tend to get cloaked by the stronger flavor profile of the cigar so, for the sake of this article, let’s move onto our brown drinks.
While these are just suggestions for you to get started, the only way for you to know for sure what couples well is to try various combinations. Start with the basic guidelines just given, and experiment for yourself. Because, after all, the only thing that truly matters is that you are enjoying yourself while puffing on a premium cigar