Spirits and Cigars
There is no straightforward answer when pairing drinks with cigars. Most of the time, it comes down to personal preference. And at the end of the day you should drink and smoke whatever makes you most comfortable. If you're enjoying it, then it's NEVER wrong.
While there is no right or wrong, there are some good guidelines you can follow before you pinpoint your specific taste. First off, you should try to match relative flavors and weight. For example, a full-bodied cigar should be paired with a full-bodied drink and a mild cigar should be paired with a delicate drink. However, keep in mind that these rules aren't always true. They are just guidelines to get you started. I would say they are more useful in avoiding bad pairings. They will NOT help you discover synergy between drink and cigar.
Then what's a great pairing? Well, truly great pairings happen when complex flavors within a cigar and spirit compliment each other. In other words, qualities that were not evident when experienced separately are suddenly there with the pairing. That being said, it simply becomes a matter of testing different combinations until you find the one that suits you. Once again, this is not an exact science. What works for one person may not work for another.
Here are a few suggestions to get you started:
Cognac is the traditional drink to have with cigars. This is largely because of timing - both are usually taken after meals, and so they naturally became linked.
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. The highest age bracket is XO, standing for Extra Old, and has a minimum ageing requirement of six and a half years, although much older brandies can sometimes be part of the blend.
Scotch, especially single-malt, is another good drink to have with cigars. Scotch will not be overpowered by even a strong cigar, and unlike cognac, you can drink scotch at any time of the day. There are hundreds of different blends of scotch available today, and you will never have time to taste every cigar with every scotch. In many cases, the differences are so subtle that it is difficult to recommend a particular pairing of cigar and scotch, but half of the enjoyment is in the experimentation.
Traditionally, rum and cigars come from a similar geographical area. Whether we are talking Cuba or the Caribbean, the people who make cigars have also made rum. For this reason, the two things complement each other very well. The cigar makers make their cigars to go with the drink they know. This has changed somewhat in the modern world; cigar-makers are not necessarily limited to only drinking rum, and thus the cigars they produce might be better suited to other drinks.
Believe it or not, it is possible to drink non-alcoholic drinks with cigars. As long as you are careful about which drinks you choose, a non-alcoholic drink can be just as pleasurable as a good cognac or single-malt scotch. One of the best non-alcoholic choices is coffee, particularly espresso, as it has strong, complex flavors, which complement the taste of a good cigar.