Cigars and whiskeys have always been closely associated. For many aficionados, they are a match made in heaven, meant to be enjoyed together. And while that is a generally accepted fact about nearly all cigars and whiskeys, there is no doubt that some cigar-and-whiskey pairings are more satisfying than others. Unfortunately, discovering the best combination to enjoy together can be tricky. A great place to start searching is in cigar and whiskey magazines where new pairings are suggested every month. Another good source is from your cigar friends. Not surprisingly, every cigar aficionado has a favorite pairing or two that they will likely share. Obviously, there is a surplus of information available, but unfortunately, the results of those pairing suggestions are often disappointing. It is a problem, I have found, that many cigar smokers share.

There are several reasons why a suggested cigar-and-whiskey pairing can fail. Often, it is the simple fact that the recommended cigars and whiskeys cannot be found locally. But, perhaps the biggest reason is because everyone’s palate is different. A perfect match for one may underwhelm another. Plus, I suspect many cigar smokers possess unsophisticated and untrained palates. For example, I have often failed to find the hints of coffee, hazelnut, cocoa, caramel, kitchen spices, and salted butter flavors, to name a few, that are said to be lurking in my cigar or whiskey. If I can’t taste the flavors, then they’re probably not doing much to enhance the pairing. And some of the suggested flavors seem like an overreach to me. Old leather and pecan shells come to mind. I’m not sure whether I really want those flavors in my smoke or drink. An obvious solution to these problems is to create your own personal pairings.

Here again, the information available in magazines and online can be misleading. Many will recommend focusing pairing efforts only on Scotch and bourbon whiskeys. Moreover, they will propose pairing cigars and whiskeys according to their strength—strong with strong and weak with weak. They also suggest carefully analyzing cigars and whiskeys to discover complementary flavors. Those are logical suggestions, but they are not without issues. First, finding subtle flavors can be challenging. Then, if you can identify them, deciding what flavors complement each other is difficult. Do the flavors of cooking spices and caramel work well together? Maybe? Additionally, I have enjoyed a wide variety of cigars with añejo tequila, rye, dark rums, ports, porter and stout beer, and even coffee. Every now and then, a mild cigar will delicately smooth out and open up a strong, high-proof whiskey for me. What these perplexing situations suggest is that less analyzing and more actual tasting are the best ways to discover an agreeable pairing. With that in mind, this is how my friend Rick and I find delicious cigar-and-whiskey combinations.

Instead of expending a lot of effort analyzing flavors, we simply begin with a favorite cigar and several whiskeys. I suppose starting with a familiar cigar is a form of unintended research into taste profiles and strengths, making it easy to understand how a whiskey is affecting the smoke. Rick and I are often less acquainted with the whiskeys we pair with the cigar, but we are somewhat discerning. We always keep the whiskeys in basic groups: bourbons with bourbons, Scotches with Scotches, and rums with rums. Sometimes we chose from a more specific group, limiting our sampling to wheated bourbons one week, high-proof bourbons the next, and Islay Scotches the following.

Once we start, we simply take small sips of the selected whiskeys while smoking the cigar. There is nothing sophisticated about this process. We are merely tasting the available whiskeys during all phases of the cigar and noting which combinations taste better together. Interestingly, Rick and I have found that nearly every cigar-and-whiskey combination was acceptable. Some were great, some were adequate, but none were disastrous. Also, because our palates differ, we rarely agreed on the best pairing. Not surprisingly, as our pairing sessions expanded with the addition of other cigar-smoking friends, it became even more difficult to reach any consensus about which pairings were the best.

Our sessions of testing a favorite cigar with several whiskeys successfully revealed many delicious pairings and just as many different opinions about those combinations. Those differences highlight how the uniqueness of every palate produces conflicting perceptions of what is delicious. That means you should experiment and discover for yourself what whiskeys complement your favorite smokes. After all, your tastes are unique, and that perfect pairing that you’re searching for is probably one that only you can discover.

Instead of expending a lot of effort analyzing flavors, we simply begin with a favorite cigar and several whiskeys. I suppose starting with a familiar cigar is a form of unintended research into taste profiles and strengths, making it easy to understand how a whiskey is affecting the smoke.