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How To Smoke Your First Cigar Properly

How To Smoke A Cigar 0 Hero
Photo: Shutterstock

Along with the discovery of the New World, explorer Christopher Columbus discovered a custom and tradition that at first seemed odd to the foreign explorers, but would soon overtake Europe and the surrounding empires at the time in a swift manner with little to no resistance. We’re talking of course about smoking tobacco, the strange plant Columbus discovered upon landing in the present-day Caribbean. It was here where he happened upon locals smoking the dried leaves of the plant, rolled up in a cylindrical manner with either dried palm or corn husks.

The earliest evidence of people smoking tobacco dates back to the 10th century Mayans, whose word for smoking “sikar” most likely had some bearing on the Spanish word “cigarro”- out of which the term was “cigar” became commonplace. Obviously, it didn’t take long for smoking to take off around the world, with Europeans spreading the habit across the world like wildfire throughout the following decades.

Needless to say, the act of smoking a stogie is nothing new. Though if it’s new to you then these tightly wound portals into the past can be a bit daunting to the novice smoker. However, once you’ve mastered the art, cigars are a great way to toast life achievements, catch up with old friends, or simply take some time for some self-introspection. And just like a fine wine or coffee bean, tobacco is flavored depending on the region and soil in which it’s grown, or how it’s wrapped. The experience is one to be relished, savored and appreciated up until the stale smoke a dead cigar butt closes out the ceremony. So if this sounds enticing, but the foundational knowledge isn’t quite there yet, we’re here to help you out though this guide on how to smoke a cigar.

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Choosing the Right Cigar

Everything about enjoying a fine cigar revolves around the notion of patience. This tradition isn’t about instant gratification. Just how cigars are a slow burn, so too should be the process surrounding the act, beginning with choosing the right cigar. Here, you’re going to want to make sure the cigar consists of 100 percent tobacco, but if you’re not sure, be sure to ask whoever is selling you the stogie to confirm. Next is the shape, (though we’ll dive more into this in a bit), but as a general rule, the length and diameter of the cigar are directly related to its intensity. So, as a beginning smoker, we’d recommend a thinner cigar as opposed to a thick and stubby one.

Once the cigar is in your hands, you’re going to want to check for quality control. Are there lumps in the tobacco? Is the tobacco discolored at the ends from improper storage, or is the wrapper itself discolored? Gently roll the cigar between your finger to assure yourself no lumps are present and take a good hard look at the condition of the roll under a light to determine no discoloring has taken place.

As for the size and shape of your preferred cigar, we’ve broken down the many offerings out there into several overarching types as to not overwhelm you. Trust us, the world out there is a large and fascinating one for cigars, but just like anything else, you must learn to crawl before you walk. So, here are the benchmark cigar shapes you need to know before walking into a storefront shop.


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As a whole, cigars boil down into two shapes: Parejo and Figurado. Parejo cigars are the stereotypical straight edged roll with a rolled head while a Figurado shape is anything that’s not a Parejo style roll. That being said, here are two common Parejo shapes you’ll find just about anywhere.

  • Corona: This is your standard stock Parejo cigar. And if you’ve casually smoked before this is probably the type of cigar you experienced. They’re typically rolled about 5.5-6-inches in length and boast a ring gauge (thickness) of 42-44.
  • Robusto: As a shorter and thicker cigar, these will offer a more “robust” smoking experience. As a general rule, they’re not typically recommended for novice smokers due to their intensity, though if you’re willing to give it a go be sure the measurements – between 5-5.5 inches in length and a 50 ring gauge – are up to snuff.


The world of Figuardos is quite vast, seeing how the definition opens the cigar world up to new and innovative rolling techniques. However, there are of course some foundational shapes to keep in mind when purchasing a cigar in this family.

  • Torpedo: What you see is what you get in this regard. A torpedo cigar can vary in length and width, however, the shape is always the same. It features a closed foot, pointed head and a slight bulge in the middle. Much like a, yep you guessed it, torpedo.
  • Pyramid: Again, thanks to a broad, open foot at the end of the cigar, tapering to a pointed and closed head, the pyramid cigar is an aptly-named and popular choice among smokers. They usually measure between 6 and 7 inches in length and boast a 52-54 ring gauge at the foot and a 40 gauge at the tapered head.
  • Perfecto: Similar to a Torpedo in shape (i.e. its closed foot and bulging middle) the main difference here is the rounded head as opposed to a pointed head. Length and thickness here can vary as well, with some Perfectos measuring up to 9-inches in length and housing anywhere between a 38-48 ring gauge.
  • Belicoso: Acting as a shorter version of the pyramid, the Belicoso typically measures in at about 5-5.5 inches in length with a ring gauge of 50 or less. Today, some feature modified shapes more aligned with a Corona but with a tapered head.
  • Presidente: Also known as the Diademas, the Presidente is the head honcho of this realm. They’re a minimum 8-inches in length with a closed head and a foot that’s occasionally open or closed as well depending on the brand. The Presidente’s ring gauge also measures between 40 and 52 as well.
  • Calebra: Spanish for snake, it’s obvious where this twisted bouquet of cigars got their name. They can be a bit of a rarity these days and are actually three cigars braided together and sold as one. However, they’re not smoked as one and are meant to be separated and shared amongst friends.
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Photo: Shutterstock

Cutting the Cigar

One of the biggest mistakes amateur smokers make is cutting the wrong end of the cigar. So before we proceed any further, it’s imperative to make sure you cut the end of the cigar that will be in your mouth (known as the head of the cigar). If and where you decide to cut the foot of the cigar depends on the cigar itself. Now for some rolls, such as the Perfecto with a pointed foot, some smokers will cut the tip off the end while others will leave it to help create a more even burn once the ember reaches the bulge of the roll. Clearly, there’s room for user preference but one thing’s for sure when you are cutting, make sure you commit to the cut, slicing in one fluid and confident motion. Otherwise, you’ll end up tearing the cigar wrapper before you even had a chance to enjoy it.

Which brings us to our next point, the type of cutter to use. Here you’ll want to use a single or double-blade cutter to horizontally cut the head of the cigar (these devices are ironically named guillotines) in a single swift motion. Now, before making that cut, you’ll want to bring the blade toward the cigar to make sure you’re cutting where you want to cut; ideally this is where the cap of the cigar meets the wrapper. Once, positioned, make a quick horizontal cut revealing the tobacco inside the cigar and gently brush off any loose tobacco from the newly sliced head.

In terms of quality cutters, there are a few out there to get you going. The majority of cigar smokers prefer guillotine cutters since they’re easier overall and more travel-friendly. Alaska Bear, for instance, makes a high-quality cutter built from brushed stainless steel and a hole diameter that fits up to a 60 ring gauge. However, one of the most recommended cutters we came across was this offering from Cuban Cutters, featuring self-sharpening double blades and a lifetime guarantee. And of course, is you wish to get fancy with it all, this carbon fiber Tonino Lamborghini Le Mans cigar cutter might be more your style.

Regardless, after making your cut it’s important to take a dry drag of the cigar to test the draw. This way you can make any necessary adjustments to the cut before moving on to the next stage of the process. Lighting the cigar.

Lighting the Cigar

We’re almost there. At this point, you’re ready to get things lit up and begin enjoying the sweet sweet taste of quality tobacco. So now that you’ve chosen the right cigar and properly cut the stogie, it’s time to the light it up. Now, before jumping the gun here it’s important to realize there are in fact a couple steps involved in getting the cigar properly lit, beginning with the lighter itself.

Ideally, you’re going to want to use a butane lighter for this, as the ammonia from matches can tarnish the flavor of the cigar. Instead, butane lighters burn at a higher temperature, producing an efficient flame that doesn’t affect the taste of the tobacco. And in case you’re in the market for a few, there are a handful of fantastic options out there that will get you started off on the right foot. For instance, this Blazer Torch Lighter will certainly get the job done, or perhaps if you wanted to enjoy the view from atop a mountain the Xikar Cirro Lighter boasts a windproof and high altitude flame for your lighting pleasure.

Now that your lighter is in order, time to light the cigar. Begin by holding the cigar above the flame. This will slightly roast the tobacco instead of automatically burning it. Pros will tell you that sticking the cigar directly in the flame will ruin the flavor. Also, at this stage, resisting the urge to smoke is crucial. Instead, you want the cigar to warm and loosen up. It’s called “priming” the tobacco. So be sure to rotate the cigar during this process as well in order to help you achieve an even burn come smoke time. Do this until you see the foot of the cigar begin to faintly glow with an orange hue. When this occurs, it’s time to smoke.

Smoking the Cigar

Here we are. Time has come to get smoking. So once the foot of the cigar is primed and ready to go it’s time to get tasting. Hold the cigar in your mouth and gently begin to draw in smoke, remember to not inhale however as cigars are unfiltered and have a much higher concentration of nicotine than cigarettes. Upon that initial first draw try holding the smoke in your mouth, savoring the flavor of the tobacco. After about 12 puffs or so the cigar should heat up enough to the point where you can remove the band from the roll.

And in case you’re wondering how to puff without inhaling, make sure you don’t draw in air from your diaphragm, instead, draw in air like your drinking from a straw with shallow breaths. Begin by drawing in like that for about four or five times once initially lit, or until the cigar begins to produce a thick white smoke.

Also, it’s important to learn how to hold the cigar with confidence, between your index and middle finger with the head (again the end you are smoking) resting on the crook of your thumb. It might feel awkward at first but soon enough you’ll get comfortable with it and look like a regular cigar aficionado.

Remember, this isn’t a race, cigars are meant to be enjoyed over the course of almost an hour. It’s a slow burn, generally taking a pull about every minute or so. This is what all that work was for, to slow down and enjoy a properly lit cigar in the company of old friends or a good read. And by God don’t forget the booze either. Pair it with a smokey scotch, a smooth bourbon or even a cognac if the moment is right. Most importantly cherish the moment, we’ve been smoking for centuries now so relish in the fact that you’re now participating in an age-old tradition that doesn’t appear to fall out of favor anytime soon. Cheers.

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Cigar Lounge Essentials

  • Xikar Silver Trezo Lighter ($80)
  • Xikar Cigar Cutter ($40)
  • Partagas Serie E No. 2 Cigar ($35)
  • Eames Lounge Chair ($6,895)
  • Derek Rose Smoking Jacket ($850)

Finally, what’s a cigar lounge without the essentials? Just a room if you ask us. That’s why if you’re going to do this right, might as well have the right gear to keep you comfortable during the nightly cigar smoking ritual. A lounge chair is necessary, and of course, a smoking jacket is imperative too. Also, a box Cuban cigars wouldn’t hurt either, now that they’re legal. Add in a triple jet flame lighter and granite grey cigar cutter with stainless steel blades in the mix and you have a recipe for an evening well spent. Now all you need is to update that bar cart with some after dinner spirits.