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There is no straightforward answer to the question of what you should drink with a cigar. A lot of it is down to personal preference. You should drink what you feel comfortable with; after all, smoking a cigar is a very personal thing, and everything about the ritual should contribute to the enjoyment. To drink something purely because it seems to be the done thing is to miss the point of the cigar.
Other factors may contribute to deciding what to drink with your cigar. The time of day for example — a cigar smoked after dinner will require a different drink from a cigar smoked in the morning. It is an inexact science.
That said, the problem of what to drink with ones cigar can often seem like an insurmountable obstacle for the novice cigar smoker, so I have attempted to provide a short guide to some of the more common drinks, in order to simplify the situation.
Striking a balance
When selecting a good drink to go with your cigar, in general you should try
to match relative flavors and weights. A full-bodied cigar calls for a full-bodied
drink, while more delicate drinks such as champagne, while they may still work,
call for a far lighter cigar.
According to Jack Bettridge at Cigar Aficionado there are two main problems with this rule: As a generalization, it is not always true, and it’s a rule that is more useful for avoiding mistakes than for discovering sublime new marriages of drink and cigar.
Truly great pairings come when complex flavors within a cigar and a spirit create synergy -- that is, attributes that were not evident come to the forefront. A dull cigar suddenly smacks of cocoa; whiskey tastes of orange peel. Both cigar and spirit develop a nuttiness where it previously hadn't been. Predicting or pinpointing the causes behind such good fortune is harder than simply matching body weights. A spicy, salty cigar might soar when paired with a sweeter spirit because the tastes complement and create overtones of toast or nuts.
With that in mind, it becomes simply a matter of testing different combinations until you find one that suits you. Some people still enjoy the traditional accompaniments of cognac or port, others prefer single-malt Scotch or rum. Even non-alcoholic drinks such as coffee have been found to go well with cigars. In fact, it turns out that almost any drink with a complex enough flavor can be a good match to a fine cigar.
Cognac
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. 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
Scotch, especially single-malt, is another good drink to have with cigars.
Taken on the rocks, or straight up, 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. The sheer variety
available means that you will be able to continue experimenting for years to
find an inspiring match for your chosen cigars.
Rum
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.
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.
Non-alcoholic 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. According to Eric
Risberg, a cup of espresso contains more than 600 different taste characteristics,
which makes it an ideal accompaniment to a medium-bodied cigar.
