How to enjoy cigars, a beginner's guide (part one)

How to enjoy cigars, a beginner's guide (part one)

Most men will never forget their first cigar. Sure, we forget our first drink; the first time we tried a cigarette; perhaps even a first kiss or first job offer. But rarely does a man forget the first time he smokes a cigar.

It was the winter of 2000. I was eighteen, and my parents went to Cuba on vacation. I asked them to bring me back a cigar. I had never smoked one before, nor been around anyone who did. My parents came home and presented me with a Romeo Y Julieta.

I was ecstatic. I took the cigar from its tube and immediately went to smoke it. However, I didn’t have a lighter. Knowing my mother would never let me smoke it indoors, I quickly fired up the stove, placed the cigar on the hot element and let it cook the foot of the cigar until it glowed red hot. Then, as fast as my legs could carry me, I darted out the back door to enjoy my first cigar.

In the depths of Canadian winter, I stood in the snow and sucked back on the end of the cigar. Nothing happened. I tried again.

What on earth? How come I wasn’t able to smoke it?

That’s when I remembered that in the movies, they always cut off the other end of the cigar. That must be it, I thought to myself. So, just like in the great mob movies of the 1970s and 80s, I turned the cigar around, clamped my teeth around the unlit end of the cigar and tried to rip off the cap. It was like biting into a stick. It was hard, and if I kept going, I’d probably end up putting my dentist’s kids through college.

So, I put out the lit cigar by rubbing it against the stucco of the house and went inside. I grabbed a serrated bread knife, placed the cigar on the counter and sawed off the cap about an inch into the cigar. Tobacco was falling everywhere. I went back to the stove to relight the cigar when my mother asked me to light it outside.

So I turned on the propane barbecue. I lit the cigar, put it to my mouth and sucked in.

How could anyone enjoy this?!?

Fortunately, after a couple of years, I took a second chance and tried another cigar, this time with the help of someone who knew what he was doing.

Since then, I have smoked thousands of cigars, hosted numerous tastings and have written many articles for dozens of magazines including Cigar Aficionado.

Steve McQueen smoking a cigar

If you open a magazine to an article about cigars, you’ll likely find that it’s geared towards the aficionado. Unfortunately, there is no cigar school. Because of this, most people either smoke their first cigars with someone they know; research how to do it properly; or have an experience like I did.

In this first part of a series on how to enjoy cigars, we’re going to focus on what you need to know to select, cut, light and smoke a cigar properly. Without any of the bad habit.

Then, in the next chapters in this series, we’ll focus on recommended accessories, how to store cigars, and how to troubleshoot lighters and cigars that aren't behaving. Finally, we’ll concentrate on recommended cigars and which sticks are worthy of your attention.

First, it’s important to note that if you’ve never tried a cigar before, it can be quite an expensive pastime and requires a relatively significant upfront expense. I highly recommend trying a few cigars before making the decision whether this is a hobby worth it to you to invest in.

The best way to begin smoking a cigar is to buy a cigar and smoke it right away. This can be done either at a local tobacconist, a cigar lounge or in the company of friends or family who already enjoy smoking.Ideally, just as you learn to crawl before you walk, it’s wise to procure a mellow to medium bodied cigar. Selecting one that’s too strong can either result in a poor experience thanks to a palate not accustomed to its richness, or worse, becoming intoxicated from the cigar which replicates the symptoms of alcohol intoxication but without the buzz.

The second most important step in selecting a cigar is to choose one that’s well made. Inexpensive machine-made cigars won’t give you the same experience as a finely aged hand-rolled cigar. Many of the cheaper sticks use chemical agents and the risk of becoming sick is far greater than if you choose one from a reputable brand.

If you’re purchasing the cigar at a tobacconist or lounge, be upfront with the purveyor and tell them you’re brand new to cigar smoking. Ask for their advice, but be clear you want a milder cigar that you can smoke in about 30 minutes and has been in the humidor for a while and therefore ready to smoke. Keep in mind that each cigar, like a fine wine, will have its own flavor profile. Just because you didn’t enjoy one, doesn’t mean you won’t like the next.

Once you’ve selected the cigar, ask them if you can borrow a guillotine cutter. Most cigar establishments will be happy to lend you a cutter.

When cutting the cap, you want to ensure you only use an actual cigar cutter. Ripping it with your teeth or sawing it as I did shouldn’t even be considered as it can destroy the cigar, causing it to unravel completely. Take the cutter, and at the closed end nearest the wrapper, find a small line wrapping around the cigar about 3mm from the end. This is where the cap was secured to the cigar and where we ideally want to cut the cigar to ensure it remains intact and that the flavor profile isn’t compromised. Taking the guillotine cutter, gently slide the blades, so they just touch the point where you want to cut the cigar. Then, in a swift motion, cut the cap clean off.

How to cut a cigar

If some tobacco becomes loose, lick the tip of your finger and use your finger to smooth down the tobacco. The saliva will act as an adhesive and hopefully, prevent the cigar from further unraveling or getting bits of loose tobacco in your mouth.

Now it’s time to light the cigar. For this, you can use wooden cigar matches or cedar strips which most tobacconists are happy to give away. However, it can be tricky enough with a lighter, so I highly recommend purchasing an inexpensive torch lighter from the tobacconist. Bear in mind that you require a torch lighter because other types of fuel can impact the flavor and aroma of the cigar.

Once you’re ready to light the cigar, hold the cigar sideways in your dominant hand so it rests between your thumb and fingers and can easily be rotated with the twist of your fingers.Holding the lighter in the other hand, ignite the lighter and slowly bring it to the cigar, being sure you can clearly see the foot of the cigar that you’re lighting. The goal here is to toast the cigar, not light it.


Think of it as a marshmallow. If you light the marshmallow on fire, it becomes burnt and bitter, but if you slowly rotate it, so it’s lightly touched by the flame of the campfire, it becomes this golden treat, so many of us crave. Cigars are much the same way. If you light it quickly, it will begin to burn too hot and affect the flavor of the cigar. Instead, slowly rotate the cigar in your fingers as the flame slightly grazes the foot of the cigar to lightly toast it to perfection. Take your time. It’s perfectly acceptable to spend a minute gracefully toasting the cigar until the entire foot is evenly lit.

Once the cigar is evenly lit, bring it up to your mouth and begin to enjoy the smoke.


Unlike a cigarette, cigar smoke should never be inhaled. The risk is extraordinary, and you will certainly make yourself sick. A cigarette is a habit, whereas a cigar is a passion. As you slowly draw the smoke into your mouth, allow it to float around your mouth being sure to let it pass over and under your tongue, against your cheeks and your gums. Then, once you’ve enjoyed the taste of the draw, allow it to escape back out into the world gracefully.

A cigar doesn’t need to be drawn more than once every 45-60 seconds. Smoking it too quickly can make you sick or cause it to overheat. Smoking it too slowly, on the other hand, will cause it to extinguish and ideally, you never want to relight a cigar.

If you spend the time enjoying the cigar and find it relaxing and flavourful, chances are cigar smoking is a journey worth taking. On the other hand, if you find it challenging, dislike the taste or are appalled by the smell, cigar smoking may not be for you. However, I do recommend giving it a second, third or even a fourth attempt as every cigar will taste different. Not to mention, you might just need to hone your skills which we will delve further into in the next chapter of this series on learning how to smoke cigars.

Until then, here are three first time cigars I recommend for the greenhorn:

1 - Davidoff Nicaragua Toro

Davidoff Nicaragua Toro

2- Romeo Y Julieta Short Churchills

Romeo Y Julieta Short Churchill

3- Dunhill 1907 Robusto


Stay tuned for part two where we will take you through the entire cigar smoking process and recommend some accessories worthy of even the most discerning gentleman’s attention.

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