We are fortunate to live in an age when there are many things available to the affluent male, from craft-brewed ales to exotic five-star cuisine. While an evening spent sampling various IPAs from around the globe may be a trendy choice, it is the old pastimes that offer the most luxurious and rewarding experiences. After all, the uniting of a fine, flavorful cigar with a balance, old whiskey tastes just as delectable in the 21^st Century as it did in yesteryears. It is a combination that has stood the test of time, enjoyed by great men like Ernest Hemingway and Winston Churchill, as well as contemporary intellectuals and captains of industry.

Of course, there is more to the experience than simply picking up any old gas-station cigar and a bottle of Jack Daniels. While the two together may look the part, they’re like a cheap suit and a bad haircut, and your experience will suffer greatly for want of an appropriate cigar and complementary spirit. The choices available to you by branching out may seem intimidating at first, but by following a few simple guidelines you’ll be well on your way to immersing yourself in an experience that you can enjoy for the rest of your life.

Choosing the Right Cigar

Much like the people who enjoy them, cigars come in a wide spectrum of sizes, colors and qualities. The first of those characteristics that you should consider when choosing a cigar is size. Although the length and thickness of the product affects flavor greatly, you should first determine the amount of time that you have to enjoy a fine smoke. If you plan on going out for 18 holes with a group of colleagues, a longer, fuller cigar would be appropriate. It should last for several hours as you make your way around the course, without fear of putting it out early. On the other hand, if you’re looking for a quick smoke after dinner and before a night out, you will want to select a shorter cigar that can burn a bit more quickly.

Your next consideration should be the boldness and flavor of the cigar, and you’ll want to select one that is appropriate for your palate and experience as a cigar-smoker. The thickness of the cigar has a lot to do with the boldness of the flavor, as this greatly determines the amount of smoke taken in to the mouth per pull. With this in mind, you will want to pay attention to the color of the cigar’s wrapper, which is itself made out of tobacco and greatly influences the overall taste. As a general rule of thumb, a lighter-colored wrapper will lead to a drier smoke, and a darker-colored one will lead to a sweeter, more complex taste. In selecting a cigar along this spectrum, you may find it useful to consult a tobacconist, who should be able to make recommendations based upon your taste and experience level.

Finally, in terms of quality, there are three basic types of cigar: handmade, machine-made and hand-rolled. Of the three types, handmade cigars are undoubtedly the highest quality and most luxurious. Cigar-makers, or Torcedors, are renowned the world over for their craft, and the quality they lend to their product is palpable to even the most undiscerning palate. Without a doubt, to have a truly remarkable experience you will want to select a handmade cigar. If you have difficulty finding these in traditional stores, you can buy cigars from online shops like JR Cigars.

Selecting a Whiskey

Much like cigars, whiskeys come in a wide-spectrum of shades and flavors. Once you’ve selected the cigar that you wish to enjoy, choosing a whiskey (or scotch, bourbon or rye) becomes a kind of balancing act. You will want to pick a spirit that can hold its own against the richness of the cigar without clashing with it or being overpowered. Therefore, you will want to do a bit of research. The Internet is an excellent resource for finding insights and suggestions in regards to the myriad of whiskey options available. However, if you’re fortunate enough to live near a well-stocked and well-curated liquor store, you may find that its purveyor is an excellent resource as well. In terms of matching the whiskey to your cigar, you will want to find a spirit with comparable tasting notes, as the interplay of the similar flavors will enhance your enjoyment of both.

One important consideration that will be apparent without any research is the proof of the whiskey. A higher proof bourbon, like Bookers, for example, will be much stronger in flavor than its 80-proof brethren. For potent spirits like these, you will want to have a bolder, richer cigar, or otherwise its flavor will be easily overtaken by the drink. You can use the guidelines to try new, adventurous combinations with the reassurance that it will most likely work. However, much like you would with a cigar, try to stick to handcrafted, small-batch whiskeys, as the difference in quality from mass-market, uncertain-vintage whiskeys is extreme.

Enjoying Them Together

When trimming the end off of your cigar with a cutter (you have one, right?), make sure that the snip is straight, as an uneven cut will lead to an irregular burn and possible unraveling. For lighting the cigar, use something with a neutral flavor. You may find a butane lighter is helpful here, but be careful! While the fuel may be tasteless and odorless, it burns at a very high temperature–you want to light your cigar, not set it on fire. Holding the flame about half an inch away and slowly puffing as you turn it should do the trick. As for your whiskey, neat is the way to go. If you prefer your whiskey chilled, consider investing in whiskey stones. These are small stones that, once frozen, can be placed in your glass in lieu of rocks to chill the spirit without diluting it. They will add immediate class to any evening, are great for gifts, and aren’t actually that expensive from places like Dean & Deluca. If, though, you do find that the flavor of the whiskey is overpowering your cigar, do feel free to add an ice cube or two to balance things out.

Now that the hard part is out of the way, all you need to do now is find a comfortable place to sit, take a deep breath, and relax. You are now participating in a tradition that has occupied the leisure time of countless great men before you. Enjoy yourself.