My parents had just returned from a three-week trip to Cuba. All I asked for was a cigar. So when they pulled out the shiny silver tube stamped “Romeo Y Julieta,” I was over the moon.

Being 18, living at home and never having smoked a cigar in my life, I decided this would be the opportune time to light it up. The problem was, I didn’t have a lighter.

So I turned on the kitchen stove, and I held the foot of the cigar to the element, and before I knew it, my cigar was lit. As fast as my legs could carry me, I ran outside to smoke my first stogie. I put the unlit end in my mouth and sucked in. Nothing happened.

“What the heck,” I wondered. Perhaps, it wasn’t lit enough. After all, only one side of the cigar was burning. So, knowing my mother would kill me if I brought smoke into the house, I fired up the propane barbecue and put my cigar into the flames.

Still nothing. Bewildered, the neighbor—a successful physician and overall nice guy—said, “you have to cut off the other end.”

This man was a genius! Why didn’t I think of that? I’ve seen gangster movies. I knew that they bit off the end. So I stuck the cigar between my teeth, chomped down and pulled. Wow, that hurt! It was like trying to gnaw through a fountain pen. Sure, I could do it, but it was so firm I’d likely need a trip to the dentist after. So, I asked my mom to pass me a knife, and when she handed me the serrated knife, I sawed my way through the cigar, taking a good inch off the top.

Partially unraveled, burnt, and yet no longer lit, I re-ignited the cigar, let all the air out of my lungs, put that mangled cigar into my mouth and inhaled like I was having an asthma attack.

It was a few years before I smoked again. I couldn’t figure out for the life of me, how anyone could enjoy a cigar.

Welcome to Cigar 101

Since that day, I have smoked thousands of cigars. My office and home are overrun with humidors, I write cigar reviews and articles for publishers like TIME Inc. and Cigar Aficionado, and occasionally, I’m hired as a consultant to help save failing cigar lounges or improve ones that are struggling.

I live and breathe cigars, and over the last two decades, I have heard variations of my first cigar experience from many men around the world.

Let me be blunt. If there was a way to screw up smoking a cigar, I’ve done it. Unfortunately, I had to learn how to smoke and appreciate cigars the hard way. But in this article, I’m going to show you exactly what you need to know so you can start your cigar journey off right—or get it back on track if you’ve been one of those guys smoking them wrong, like I did.

What Equipment Should You Have?

If you’re not sure you’ll even enjoy smoking cigars, don’t waste your time buying expensive equipment you may never use. All you’re going to need to start is a cutter, a lighting source, and a well-aged cigar. Aside from that, a re-sealable freezer bag, a new sponge and a room temperature bottle of water.

The Cutter

A cutter is an invaluable tool. It has one purpose and that is to cut the cap of the cigar off. Where I went wrong was trying to bite it, then attempting to saw it, and all-the-while, doing it on a cigar that had sat in my father’s suitcase for three weeks because they bought it their first day in Cuba.
There are a number of different cutters, all of which have their benefits. If you’re new to cigar smoking, the kind  I recommend is a guillotine cutter.

You don’t need anything fancy. In fact, I recommend the Cuban Crafter’s Perfecto cigar cutter. Unlike most guillotine cutters, this one is made for beginners. It’s the kind I suggest that cigar lounges keep stocked, and the plastic version costs less than $10. What separates it from the pack, is that it has a series of calibrated chambers that allow you to achieve the perfect cut on any shape cigar. One mistake often made is cutting off too little or too much, and this ten-dollar cutter takes the hassle out of the cut so you can be assured you don’t butcher the stogie.

Lighting Source

The Torch Lighter

Unfortunately, using the range on your stove or the barbecue isn’t an adequate lighting source. In fact, neither are most lighters. Using a gas-station BIC or Zippo is going to alter the profile of the cigar, so if you want a lighter, you need a torch lighter.

Like anything, there are some you can buy for under $10, and there are others—like the ones from S.T. Dupont—that cost more money than some people earn in a year. At first, I don’t even recommend buying a lighter. Unless you already know you’ll enjoy smoking cigars, or you have other uses for a torch lighter (think creme brûlée), most tobacconists will give you free cigar matches when you buy a cigar from them. If you do want a torch lighter, remember you’ll also need to buy quality butane such as Xikar, which is the one I recommend for most lighters.

As far as the quality of lighters goes, most tobacconists will have a fairly large selection to choose from, and will often fill it with butane on the house. If you intend to smoke outdoors, I suggest investing in a wind-resistant lighter.

Cigar Matches

Cigar matches are great for the greenhorn. Often free with purchase from the local tobacco shop, they’re a good option if you don’t want to spend money on an item you may never use again.

The downfall with matches is they can be tricky to use. Matches don’t get as hot as the flame from a lighter does. So, you may find that you need to use a few of them to get the cigar lit. It will take a little longer, and you’ll need to let the match burn for a second before lighting the cigar so that you don’t end up transferring sulfur to the tobacco.

This can be a little cumbersome for new smokers, so I suggest asking the tobacconist for cedar strips instead.

Cedar Strips

In my opinion, cedar strips are one of the most elegant ways of lighting a cigar. A thin and long strip of cedar—which is also used inside most humidors—can be used as an intermediary heat source to light your cigar without impacting its taste or aroma.

This is particularly useful for those who—like me—have to resort to a barbecue or stove to light the stogie. Instead of taking the heat source directly to the cigar, you light the cedar strip and then use that to light the cigar.

Cedar strips, like matches, are relatively easy to procure. Most tobacconists will have them available, and often, they’re happy to give some away with purchase.

Since the flame is less controlled with a cedar strip, use your hand to re-position the strip as you light the cigar. This way, you can slow the burn down or speed it up a bit. You may need more than one strip to enjoy smoking your cigar, so make sure you’re set up with at least a few.

The Well-Aged Cigar

When it comes to buying your first cigar, you want to make sure that the cigar is well aged and ready to smoke. The standard rule of thumb is a cigar should sit in a properly regulated humidor for at least six months, but if you don’t have a humidor, that can be problematic. So, if you plan to smoke the cigar right away, you’ll want to purchase it from a tobacconist or cigar-friendly establishment that has already been aging the cigar.

This is important to ask because rarely can a purveyor guarantee whether a cigar is ready to smoke, if it’s a new arrival. It’s possible that cigar may be just fine, but it’s also possible that it sat in a warehouse waiting to be inspected by customs, or that it spent months on a loading dock, before being shipped to your location. When a cigar has been exposed to humidity levels that are too low or too high, that can significantly impact the way it cuts, lights and smokes. Since, as a new smoker, it may be difficult to tell based on appearance, touch or scent how ripe the cigar is, you’ll have to ensure you are dealing with a reputable shopkeeper you can trust.

Saving It For A Special Occasion

Many men don’t intend to smoke their first cigar right away. Perhaps you’re saving it for a poker night with the guys, or to share one with your father-in-law after you announce his daughter is pregnant. Or maybe, you just don’t have the time to smoke it right away.

Purchasing a cigar and then leaving it to rest does nothing besides harm the experience. Cigars require very specific environments, which is why collectors store them in humidors. The humidity levels and temperature need to be precise. Leaving it on the counter, in your desk drawer, or freezing it won’t make for a fun experience whether you decide to smoke it the next day or next month. What’s worse, is that unless you have a good friend who is willing to store it for you in his humidor, purchasing a humidor and the required accessories can be expensive if you don’t even know whether you’ll enjoy it.

Thankfully, there is a hack for creating a makeshift humidor.

The Makeshift Humidor

You can use any sealable container, but I recommend a plastic Ziploc bag, a plastic container or even a cooler. You will also need a humidification device. For this, you can use a new sponge dampened with some distilled water, but I recommend the individual Water Pouch Portable Humidifier bags from Cigar Caddy. Simply place the humidifier in distilled water for 15 seconds and then put it back in its reusable bag and place it in your container. It should keep your cigars fresh for at least two months if not three.

Most well-stocked tobacconists will have the Cigar Caddy pouches on hand, but if not they’re relatively inexpensive to order off Amazon, eBay, or a handful of the online tobacco shops.

Selecting Your Cigar

There are scores of different cigars from all over the world. Like wine, each cigar will have its own flavor profile. There are mild, medium and full-bodied cigars to play to any palate.

As a new cigar smoker, I encourage you to stick with a cigar from one of the following countries:

• Cuba (if legally permitted)
• Nicaragua
• Dominican Republic

The prices of an individual stick can vary dramatically. Some cost just a couple of dollars, whereas others can cost well over $100 for a single cigar. The phrase “you get what you pay for” can sometimes ring true. However, when it comes to cigars, so long as you follow the tobacconist’s lead and stick with a cigar from one of the countries mentioned above, you’ll end up with a cigar that is worthy of your discerning tastes. Even if you just spend $10.

Cigars also come in a range of different shapes and sizes. For the most part, the shape and size selected by a seasoned enthusiast are based on his personal preference, the qualities of the cigar and how much time he wants to invest in smoking it. Unlike a cigarette, cigars can take a fairly long time to finish. It isn’t unusual for me to enjoy a cigar for two hours.

Cigar sizes are determined by two measurements: the length of the cigar, and the ring gauge, which is a fraction of an inch measured in 64ths. While it may score you some cool points going with a large ring gauge, it could also end up being something you’ll regret.

Instead of trying to get into specific sizes and shapes, ask the tobacconist to point you in the direction of a standard Robusto.

The Robusto is a great introductory style because it’s a comfortable size, but it will take less than an hour for you to smoke. Unlike some cigars that are larger and smaller than it, the Robusto is a great size and shape to give you that opportunity to see how a cigar changes as it’s smoked and to determine whether you enjoy the experience.

The biggest tip I can offer you is to stick with a mild or medium-bodied cigar. Even if you enjoy fine single malt Scotch or you’ve been a cigarette or pipe smoker for the last two decades, a full bodied cigar will literally knock you on your ass.

It’s called being “cigar drunk,” and it sucks.

If you want to know what being cigar drunk is like, down a bottle of cheap tequila and tell me how you feel. It’s one of the worst experiences new—and even experienced—cigar smokers can have.

The symptoms of being cigar drunk are similar to being intoxicated off alcohol but without a buzz. You will likely feel lightheaded, but you’ll also feel nauseous and dizzy in ways you’ve hopefully never had to experience.

Just because a cigar is mild or medium-bodied, doesn’t mean it’s not as good as a full-bodied cigar. In fact, many of my favorite cigars are milder, as are most of the cigars that receive the highest ratings and reviews.

Now, opting for a mild cigar isn’t a guarantee you won’t get cigar drunk. This is why instead of getting a large cigar, I suggest something slightly smaller. Because even if you drink light beer, you’ll still get drunk if you drink too much.

How to Choose Your Cigar

Don’t. That’s really the best advice I can offer. Don’t choose your first cigar. Instead, let a trusted friend who enjoys cigars help guide you, or ask the tobacconist for assistance.

Your best bet is to be honest. Walk into the cigar store and tell the shopkeeper that you’re interested in getting your first cigar and you’d like something mild and easy to enjoy so you can hopefully take pleasure in the experience. You may have heard that the color of the tobacco is an indicator of how strong the cigar will be. That’s not always the case though, and if the tobacconist wants your repeat business, he will take the time to lead you in the right direction, so you’ll come back begging for more.

How to Cut, Light and Smoke Your Cigar

Now that you’re ready to smoke your cigar, start by examining the cigar’s appearance and gently rolling the length of it between your fingers.

As a new smoker, you won’t be doing this to try and ascertain the flavor profile or critique the cigar. You’re doing this to ensure the cigar smells good throughout, doesn’t smell moldy and that the firmness of the cigar is consistent throughout. If you notice soft spots or hard spots, those can be indicators that the cigar wasn’t rolled properly, and you may find that the cigar either burns too hot or the draw (how much smoke comes in) is impacted when you hit those spots. If you do have some firmer spots, gently massage them between your fingers in a rolling motion, being careful not to impact the construction of the cigar.

Cutting the Cigar

The first step is to cut the cigar. If you’re using the recommended Cuban Crafters Perfect Guillotine Cutter then you won’t have to worry about where to cut the cap. The cap is the closed end of the cigar, closest to the paper band that’s likely wrapped around it. If you look at the cap closely from the side, you’ll notice that there is a line about 3mm or so from the end. This is where the cap was secured to the cigar which kept the wrapper from unraveling.

Right before the end of the cap is where you ideally want to cut the cigar. Cutting it too close to the end can result in difficulty drawing from the cigar, and cutting it too far from the end can cause the cigar to unravel. This is the end of the cigar you’re going to be putting your mouth on, so it’s ideal if you’re not getting small pieces of tobacco leaf stuck to your tongue or lips.

Tip: If you notice there are some loose bits of tobacco after the cut, lick the tip of your finger and gently use it to glue down the leaf.

To make the cut, you need to be decisive. The best way to cut a cigar using the guillotine cutter is to position the cigar between the cutter’s blades, so there is just enough tension to prevent the cigar from slipping. Once you have it positioned, hold both sides of the cutter and make a swift cutting motion to snap off the cap cleanly.

The next step is to light your cigar.

Lighting the Cigar

Regardless of whether you are using a torch lighter, matches or cedar strips to light your cigar, the goal is to toast it gently.

Forget the movies, and instead of clutching the cigar between your teeth and sucking back as you light, hold it in your dominant hand between your thumb and forefinger. Slowly rotate the cigar like it’s on a spit and holding the heat source slightly away from the foot (the lighting end), toast it gradually and evenly as you rotate the cigar.

This is kind of like roasting marshmallows over a campfire. Put it too close to the flame, and it lights on fire, but hold it just close enough, and if you take your time, it will become golden brown.

Once your cigar is evenly lit all the way around, you’re ready to start enjoying it. The reason we didn’t put it in our mouth and suck on it as we lit it, is because sucking on it draws the heat in and will cause it to burn too hot. When a cigar is too hot, its flavors react like a body on steroids and become far too potent, not allowing you to appreciate it the way it was intended. For new cigar smokers, it can continue to burn too hot and develop bitter flavor profiles that can be off-putting.

Smoking the Cigar

To smoke a cigar, hold it between your thumb and fingers, rather than between the V of your middle and forefinger like you would a cigarette. This is nothing like a cigarette. Cigarette smoking is an addiction, whereas cigar smoking is an experience.

Once you put the cigar to your lips and take your first draw, you also have to remember that unlike a cigarette, you should never inhale cigar smoke. Not only can it make you instantly sick, but inhaling the smoke from a cigar is far more dangerous than smoking cigarettes. The goal isn’t to inhale; it’s to enjoy the flavors.

As you take a draw from the cigar, do it slowly and try to focus on the depth of flavor you get as the smoke enters your mouth. Allow the smoke to linger in your mouth—being sure not to inhale it—and then release the smoke back out.

Cigar smoking should be a relaxing and leisurely escape. This isn’t something you do on your lunch break during a hectic day at work. That’s what vodka is for. A cigar is something you enjoy on a pleasant evening in your favorite chair, with Miles Davis playing in the background and a good book to read before bed.

You should be able to enjoy one draw roughly every minute while still keeping the cigar lit, and preventing it from burning too hot or getting cold. Don’t be alarmed if you have to re-light your cigar once or twice at first. While it’s not ideal, it can happen if you leave the cigar too long or the draw is somehow impacted. If it begins to burn too hot and you can feel your fingers getting warm, slow down and let the heat cool a bit before taking your next draw.

You’ll notice that the entire profile of the cigar may change as you progress down the length of the cigar. You may love parts of it, and dislike others. Just remember that every cigar, like wine or whiskey, is different. Chances are you won’t like all of them.

Once the cigar gets to its last quarter, it will begin to burn hotter. You are not expected to smoke it right down to the foot. Feel free to let it die gracefully with a few inches to spare. But, again, unlike a cigarette, remember that most quality cigars were handmade by artisans who spend their lives trying to craft the perfect blend of tobaccos. Cigars are their art, so rather than disrespect the cigar by thrusting it into the ashtray, just lay it on its side and allow it to take its last few breaths with some dignity.

Recommended Cigars:

Romeo Y Julieta Short Churchill
Davidoff Nicaragua

You might also like...

21 Ways to Thrive When You Have No Motivation to Do Anything

101 Motivational Quotes on Being a Gentleman

Table Manners 101: Basic Dining Etiquette