When it's time to explore the decadent side of life, you'll be hard-pressed to do better than enjoying two bold indulgences: whiskey and cigars. And with just a little guidance, learning to pair the two can actually enhance the experience of both, treating you to the opulent luxury you deserve.The world's best cigars and whiskey share one common trait: they are both crafted with an aficionado's care and individual taste, creating a vast array of flavors that spans the gamut. Pairing them is almost as much an art as their creation, but a few simple guidelines can steer the uninitiated in the right direction.When smoking a cigar, be sure to give yourself time to fully enjoy the flavors it has to offer. You shouldn't puff any more often than every minute or so, and don't inhale the smoke. Likewise, sip your whiskey slowly and focus on how its unique flavor blends with the taste of the cigar.Both cigars and whiskey can be characterized as either mild or strong, and a good way to start off your exploration of pairing is to try matching a mild cigar with a mild whiskey. Mild cigars like the Houndouran Casa Toranos, the Cuban Romeo and Juliet Vintage, or the Dominican-made Macanudo Hyde Park cigars are nutty and somewhat sweet, and go well with a nicely balanced bourbon like the Van Winkle Lot B, or a slightly aged Dewar's 12-year scotch.Strong and mild can also refer to the amount of nicotine in a cigar, or the proof of a whiskey. But for the sake of pairing, you should concentrate more on the depth of flavor in each, and which ones serve to best complement the other.Strong cigars can be characterized as being rich, robust, or even peppery to the taste––Hemingway Classic Sun Grown cigars, Arturo Fuente 858 Rosados, and Leon Jimines 300s meet up well with the equally bold flavors of bourbons like Booker's True Barrel, Blanton's Single Barrel, or any reputable single-malt scotch aged over 20 years.Once you start to get the feel for what's out there, you might enjoy contrasting the flavors of strong and mild cigars and whiskeys. And remember, no matter what anyone else says, it's your palate that's the ultimate judge.Pairing a strong cigar like the Romeo and Juliet Reserve Maduro with a cognac-like Sazerac Kentucky Straight Rye Whiskey or the solidly medium and maple-sweet Maker's Mark are sublime combinations that aim to please. Likewise, a super-peaty 20-year Laphroig can be assuaged by the soothing mellowness of a Macanudo.And definitely don't be afraid to stand on the shoulders of giants here, and read up on other specific pairings tried and approved by world-renowned enthusiasts. Once you have a good feel for which pairings appeal most to you, branch out and experiment on your own, and you just might discover the next magical combination.I'm Jonathon Stewart with Your Best Life.