Cigars are fine, but a cigar and a drink? Damn fine, indeed.
Now, if you're here, you're wondering if there are guiding principles behind pairing cigars and drinks. And there are! Here are some basic thoughts:
For a result that generally works, try to match flavors and strength levels. For example, dark oscuro wrapper cigars and 1) espresso, 2) a strong stout, or 3) a potent brown liquor (like bourbon). Or, on the other end of the spectrum, a nice blonde mild cigar and 1) a wheat beer, 2) a new coffee you've wanted to try, or 3) an easygoing port.
Of course, this isn't a hard and fast rule. The piece of advice that serves you best will be to experiment. There are definitely wrong answers on the pairing test. And if you experiment, you're sure to find them. But if you go against the rules, you might find some things that are fantastic. A strong smoke may overpower a weak drink... or it may accentuate a particular flavor that makes the experience worthwhile. A strong drink may shine with a weak smoke - you never know until you try.
The worst that happens is, you say, "Gross. Not doing this again." (It's the same risk your wife takes when you talk her into something sordid in the bedroom, and she's survived the marriage so far! You can be just as courageous.)
Remember, the goal is to taste things that are interesting together. Each flavor will be influencing each other flavor. So take things slow, see what works, and enjoy the ride.
Here's the basic list of drinks to start with:
- Brown liquor (dark rum, whiskey, bourbon, cognac, brandy)
- Coffee, especially espresso
- Wines, especially reds and ports
- Beers, especially porters and stouts
