So, you want to grow a little hair on your chest and light up a delicious, one-of-a-kind smoke and get into the handcrafted goodness that is the modern cigar industry. Great, grand, wonderful. As a brother of the leaf myself, welcome. Why don’t you pour yourself a drink — if you don’t want anything heavy, coffee or soda works, too — take a seat, and let’s get you ready to embark on this adventure. This guide to smoking a cigar will walk you through every step, every stage, every rule in the process. When I’m done with you, you’ll be a veritable Churchill in the making. Indubitably.
Of course, there are some things you need to know first. Keep in mind, everything I’m going to share is, as Captain Barbosa says, “more like guidelines than rules, really.” Doing some of the things I advise against will just make you look like a fool, in most cases. If you want to be a rebel, go for it. However, I will make it clear when a certain activity or habit is disrespectful — you’ll see what I mean when we get there.
“[…] I must point out that my rule of life prescribed as an absolutely sacred rite, smoking cigars and also the drinking of alcohol before, after and if need be during all meals and in the intervals between them.” — Winston Churchill
You have to know already, I’m smoking a cigar while I write this. A Boneshaker Lunatic. It’s delicious. Let’s get this thing ignited.
Cigar advice to kick off this guide to smoking a cigar
Respect the craft — Cigars are the culmination of no fewer than 300 hands. Many people put their blood, sweat and tears into making these unique products. Try to be mindful of that.
Enjoy it to the fullest — With number 1 in mind, it’s also important that you enjoy your experience. If you’re not having a good time or don’t like the flavors in the cigar, put it out.
Cigars are both solitary and social — Choose how and where you want to smoke beforehand. More specifically, who you want to smoke with. It absolutely affects how you experience a cigar. Smoking alone is excellent for relaxation and recovery, but there’s nothing wrong with making it a social activity, either. Just be advised, smoking in the wrong company is going to make it suck.
Pair with a sweet drink — Water and hydration are important, but with your first cigar, you don’t know how you’ll react to the nicotine. People get sick because they either smoked too fast or don’t pair with something sweet, which helps offset the nicotine effects. Soda is good, but if you’re watching sugar intake, you can also go with tea, juice, coffee or sparkling water. Whiskey, bourbon, scotch, gin, tequila, and beer, are also obvious choices.
Don’t inhale —Just don’t. There are some idiots who say they do. They’re idiots.
Find your palate — Everyone has a different palate. You might pick up similar flavors as your buddies or you may not. It depends on what you’ve eaten, what you’re drinking, and how sophisticated your palate is. There will be flavors you don’t like. Learn to trust in that and you’ll find your top cigars in no time.
Learn to retrohale — Your tongue can only pick up so many flavors. If you’re only drawing smoke into your mouth and exhaling, you’ll never get the full experience. Learn to retrohale. It is exactly what cigar makers want you to do.
Pay it forward — The cigar community is generous, as you’ll soon find. You may meet people who offer cigars, invite you to social events, or send you cool shit. There are no rules for these experiences other than it’s an unspoken agreement you always pay it forward when you can. Eventually, you’ll know enough to take another newbie under your wing or share your favorite smokes.
Choosing your first cigar
Source: Briley Kenney / The BS Lounge
The community is great and you’ll discover a lot of fantastic advice. Unfortunately, I often come across some pretty poor cigar recommendations for those who are just starting. There are a few reasons for this, namely, experienced smokers have tried a lot of different options and it’s easy to forget what it’s like when you light up your first.
I’m not saying anyone is wrong, nor that you should never take advice. But you want to come into this craft on your own, especially at the start. You should choose your own cigar entry point, if you’re up for it.
Begin with something light and by that I mean no stronger than a medium-bodied cigar. You might also consider going with a much smaller vitola like a Robusto. The bigger the cigar, the longer it takes to smoke, and the more exposure to nicotine — that can lead to getting nauseous or sick.
Start small, win big.
“A best practice for everyone, and I do mean everyone, is to experiment. Don’t be afraid to try something new, even if you have smoked for years.”
Great cigar brands for beginners
Arturo Fuente
AVO
Cohiba
Davidoff
Kristoff
Macanudo
Montecristo
Nub by Oliva
Oliva
Partagas
Perdomo
Rocky Patel
Romeo y Julieta
The brand doesn’t really matter. Some people will tell you Davidoff is the best, Fuente is the best, Cubans are the best — you may agree with all of that or none of it.
Flavor profile doesn’t matter as much either, because starting out you’ll have no idea what you like. Again, just remember to start small and light and work your way up from there, after you’ve had a few cigars. If you’re buying online, cigar retailers include this information with each cigar listing. When you’re buying in a lounge or shop, you can always ask an employee or an attendant.
You need tools before you can tackle this guide to smoking a cigar
Source: Briley Kenney / The BS Lounge
You’re going to need some gear to get started. You can start cheap. I would avoid buying expensive accessories like ST Dupont gear until you know you’re sticking with the craft. If you find the right mentor, they might even gift you the necessities.
Basically, here’s what you’ll need:
A cutter (straight/guillotine, punch, V cutter or scissors)
A torch lighter
An ash tray or something to toss your ashes into
A place to smoke, preferably outside
A delicious beverage to pair with your cigar
If you buy cigars through any retailer, online or not, you can usually find bundles that include freebies. That’s a great way to get your hands on some cheap but viable cutters, lighters, and ashtrays. You don’t always have to buy full boxes to get the deals either. Good places to check include Cigar Page, Best Cigar Prices, JR Cigars, Cigars.com, Atlantic Cigar Company, and if you’re feeling lucky, Cigar Bid.
Keep it simple, newbie
While there are several ways to light your cigar, including a cedar spill, I would recommend against doing anything exotic for your first few times. There’s an art to lighting a cigar even with a torch lighter, which is one of the easiest methods, so you don’t want to get too advanced from the get-go.
Torch lighters take butane, so you might need some of that, as well. Also, it’s entirely possible to torch the shit out of your cigar, burning it too much. So, take it easy. A single flame or multi-flame torch is still one of the most reliable ways to light a cigar, especially one with a big ring gauge.
Guide to smoking a cigar: Double check the conditions
Before lighting, you’ll want to make sure the cigar is humidified correctly. Too wet or too dry and it’s going to burn hot and funny. That will also make the experience poor for you, and could even sway you to stop smoking altogether — a bad burn can ruin everything, especially flavors.
Hold the cigar between your thumb and index finger and pinch slightly. It should be a little squishy, enough to where the cigar compresses easily, and you don’t hear any crackling. You’re not strong-arming the cigar, so keep that in mind, you should still be gentle here.
If it cracks or it’s too tight, it may be under-humidified or dry. If it’s too squishy, then it’s likely over-humidified and too wet. You want it somewhere in between and just right. It will take a few tries before you can really pick out the ideal feeling.
For a dry cigar, you want to put it back in a humidor and let it acclimate for longer. For a wet cigar, you want to leave it out for a day or two to lose some humidity and dry out. If you just bought the cigar from a store or lounge, talk to an attendant, they might allow you to exchange for a more optimal stick, if you haven’t opened or cut it yet.
Cutting your first cigar
Source: Briley Kenney / The BS Lounge
Source: Briley Kenney / The BS Lounge
Source: Briley Kenney / The BS Lounge
I recommend going with a straight cutter, also called a guillotine cutter, for your first few stogies. You can experiment with other options later. It’s all about the experience they offer, like a loose versus a tight draw, and you won’t know the difference, or what you prefer, until you’ve had a few.
The downside to a straight cutter is that it’s very easy to cut too much off the cigar. You want to barely trim the cap — the layers of tobacco covering the head of the cigar for protection. We’re opening the end of the cigar so that the smoke can pass through as the tobacco burns, and the flavors with it. You don’t want to butcher the wrapper, which is the outer layer of tobacco, as that is what will provide most of your flavor.
If you’re using someone else’s cutter or a community cutter, like one at the lounge, don’t lick the cigar beforehand and don’t put it in your mouth until after it’s cut. I think it’s fairly obvious why, but people still do it and it’s gross (if you do this, you’re a dirty bastard). I’ve seen people deep throat cigars before, no joke.
That’s one reason why I always carry my own cutter with me. If it’s yours, all bets are off and you can chew on the damn cigar beforehand, if you so desire. Just avoid sharing your cutter if you like to slobber.
Alternative cigar cuts include:
A punch — The tool bores a small hole through the head, allowing smoke to pass through a tight, concentrated opening.
V-cut — The tool makes a V-shaped cut in the head of the cigar, similar to a punch, with improved airflow and draw.
Scissors — Meant to be portable, cigar scissors allow you to trim the cap with better precision than a straight cutter.
X-cut — Using a V-cutter, you make two cross-cuts in the shape of an X at the head of the cigar.
If you have no tools, you can also get by using your fingernail to cut and pick apart the cigar cap. Just press against the edges of the cap with your nail. It’s easy to crush the cap if you’re not gentle, which is why I don’t normally recommend this method.
Although the picture above depicts this, and many smokers do it this way, I don’t recommend holding the cigar in your mouth the first time you light one.
Hold the lighter in one hand and the cigar in the other. Treat your cigar and lighter like you would a paintbrush and a canvas. Touch up the end of the cigar as you start the burn. Roll it ever so slightly, so the flame ignites the entire foot. You want a nice orange cherry, with a small amount of white ash visible. Try not to charr the foot (like I did in the video), but it happens sometimes. It helps to take a draw or a puff, to heat the cherry, and then blow on the foot, which achieves the same.
“If heaven has no cigars, I shall not go there.” — Mark Twain
The biggest tip here is to pay attention. At least for your first couple of cigars, watch what you’re doing with the lighter. Don’t get distracted, don’t be talking, and don’t look away until you’re done igniting the tobacco.
It’s not rocket science, but if and when you do light your cigar wrong, it can mess with the burn. Outside of poor construction at the factory, that’s when you can run into uneven burns, canoeing, and other issues.
The ultimate guide to smoking a cigar: Actually smoking
Your first cigar is lit. It’s exciting and you feel like a badass, I get it. You will be tempted to continue puffing or drawing in smoke often. Try not to smoke too fast. Smoking is a slow, deliberate process when you do it right. That’s why a lot of people love the experience. It’s a chance to kick back, relax, and really enjoy yourself as opposed to the fast-paced, always busy world of today.
“There’s […] etiquette required in a cigar lounge, right? Other than that, it’s about conversations, camaraderie, but above all personal taste. So, if somebody tells you that you can’t enjoy a cigar together with a beer, that’s personal preference. Whatever rocks your boat. Venture out, there’s a whole universe of cigars to discover. You can go very broad and very deep, or just smoke them occasionally.” — Karaoke Andi, Legend and Cigar Expert
This is why it’s necessary to have an ashtray nearby, or even a cigar stand. Take a couple of puffs, draw the smoke into your mouth, let it rest for a sec, retrohale, and take in the flavors and aromas. Then, put the cigar down for a minute or two. A well-constructed cigar will not go out on you. But if you’re puffing too often, that keeps the cherry hot and also encourages the tobacco to burn hot. As mentioned, that can ruin the entire experience.
Between puffs, the cherry should cool enough to where it’s not lit up and bright orange. You’re looking for a dull hue behind the ash. A great way to test if your cigar is burning hot is to take your thumb and index finger and hold the cigar about a half inch from the ash line. If it’s too hot to touch, then your cigar is burning way too quickly and hot, for whatever reason. It should be warm but bearable to hold.
A cigar burning too hot is why you hear a lot of new smokers say they could only taste smoky flavors. Either they were smoking too fast or they didn’t pick a cigar that was cared for properly. You might assume that all lounges and cigar shops keep their cigars perfectly stored, but that’s really not the case. I’ve had many, many cigars that were over or under-humidified right from the lounge’s humidor.
It sucks when that happens, but that’s out of your control. What is in your control is how fast you smoke. Slow down. Take in the aromas and flavors. Enjoy yourself. It’s not a race, and no one cares how quickly you blow through a stogie. I know people that take hours upon hours to smoke a robusto-sized cigar, which is pretty wild. It also shows the kind of attitude you should have with your own smoking sessions.
For the love of God, retrohale. Don’t do it once per cigar. Do it, at the very least, several times per third. Cigars are divided into thirds: first, second, and third. Some remain consistent all the way through, but for most cigars, they evolve as you smoke by introducing new flavors. The only way you’ll pick up a lot of those nuanced flavors is by retrohaling.
Retrohaling involves pulling the smoke through your nasal cavity and out of your nostrils without inhaling. It works best when you have cool smoke, so draw it into your mouth and let it sit for a second or two. Push your tongue to the roof of your mouth, slightly in the back. Then, pull the smoke up and out. That draws the smoke across your olfactory senses, letting you taste many, many more flavors than just what your tongue can pick out. It takes practice and you won’t get it right away. That’s okay. But work towards being able to retrohale every time you smoke.
When you first do it, you might notice the cigar burns a little more, especially if it’s stronger. This is usually the pepper or baking spices in the tobacco that everyone talks about. Even if you don’t like that sensation, keep at it. Eventually, you’ll build up a tolerance.
Otherwise, enjoy your cigar. Congratulations, you’re well on your way to becoming a true cigar aficionado.
The three fingers rule is a good one to follow, or you can use the cigar bands as a guideline. From where you cut the cigar at the head, place your index, middle and ring fingers together and gauge the distance of the ashline. If it’s at or past your three fingers, you can put out the cigar. Alternatively, just stop when the ashline reaches the secondary bands. If you’re enjoying it, by all means, continue smoking. Some people will smoke down to a nub.
The true signal of a cigar’s endpoint is where it starts getting uncomfortable. When it starts burning your lips, tongue or mouth, it’s time to put it down. You’ll know the difference between that and your regular smoking experience. The cigar gets just a bit too hot to bear. Sometimes, the cigar never gets there and you can smoke it all the way down.
How do I put out my cigar when I’m done?
If you’re at a lounge or an event, don’t stamp, crush, or toss the cigar into the ashtray. Not only is it disrespectful, it can make a mess. Instead, put the cigar on the rest or down inside the basin and let it go out on its own.
Now, if you’re at home, alone, who cares what you do? Etiquette doesn’t matter as much when it’s just you or a couple of close buddies. Chuck that cigar to your heart’s content. If you get hot ash all over your guests, they might have something to say, though.
When do you remove the band?
You can remove the band anytime you want, but a good, secure band might give you a little trouble if the cigar is cold. Cigar manufacturers use a type of food-safe glue called pectin. As the cigar burns, and the ashline moves up the cigar, the rest of it gets hotter. It’s common sense. But the closer that warmth is to the bands, and the glue, the easier they are to remove.
If you try to remove them too early, you risk cracking or ripping the cigar wrapper. That’s why it’s a good idea to wait until the ashline creeps fairly close to the bands.
Obviously, any bands on the foot or extra inserts, like a cedar covering, should be removed before you light the cigar. But I think even beginners will know that already.
What if the cigar won’t stay lit?
If you’re having issues where the cigar just won’t stay lit or isn’t burning evenly, you can try to touch up the foot with your lighter. I’d recommend tapping off any ash first. Touch up the areas that aren’t lit, or roll the cigar foot across the flames as you did initially. You can also use the lighter to touch up the exterior wrapper when there’s a portion that’s burning faster, just be careful not to charr the tobacco.
“Smoking cigars is like falling in love. First, you are attracted by its shape; you stay for its flavor, and you must always remember never, never to let the flame go out!” — Winston Churchill
What if I don’t like the cigar?
Put it out. We’ve all been there. No one will get upset with you if you’re genuinely not enjoying the cigar.
If you keep wasting cigars, then you might get a few comments, but why would you do that, anyway? That’s a lot of money down the drain.
I tried a few, and I still don’t like it? What should I do?
Don’t force it. If you don’t like it, you don’t like it and that’s okay. Cigars aren’t for everyone, but there is a cigar out there for everyone. What do I mean by that? Again, some people are never going to enjoy smoking a cigar. But there’s a difference between not liking the experience at all and not finding a cigar that’s right for your palate.
No one can tell you what to do here. It’s really about knowing yourself. But you can absolutely find a cigar that matches your personal tastes. Whether you like sweet, extra peppery and strong, very mild, or the gamut of flavors from fruits and vanilla to ginger, earth or even lemongrass. Infused cigars, Cuban-seed cigars, and cigars with mild, medium, strong, light, or dark profiles exist; it all depends on your preference.
You’ll get recommendations all day long about brands, blends, and various labels. I’m not saying ignore them, but you have to understand enthusiasts share through the filter of their own palate. Most likely, yours won’t be the same. The best practice for everyone, and I do mean everyone, is to experiment. Don’t be afraid to try something new, even if you have smoked for years.
Can you relight a cigar or put it out and save it for later?
Technically, yes. There are all sorts of guides for doing this. I would not recommend it. On average, a cigar takes between an hour to two and a half hours to smoke. You should plan to smoke the entire thing before you sit down to enjoy one.
Now, there are absolutely situations where you might let one go out for a few minutes. A great example is if you light up before dinner. When the food is ready, you can put down your cigar and let it go out. If you’re coming back out within the next couple of hours, you can just relight, or trim from the ashline a bit and light up again. I will say, learn to purge the cigar first before you try that. It can get rid of tar buildup in the foot or chemical flavors you might taste.
But if you’re putting it out for any longer than a day, with plans to come back, you’re on your own. I would just put out and toss the cigar at that point, personally.
My cigar cracked; what do I do?
Remember that cigar glue I talked about? Pectin? You can actually buy a vial and use it to repair your cigars. I will say some cigars are not worth recovering. That threshold of breakage is really up to you, though.
A broken or cracked cigar, even repaired, probably won’t burn right, which makes for a sub-par experience. But if you spent a lot of money, it’s hard to give up a cigar. Trust me, I get it. That’s when you can try repairing with the glue. It’s easy, too. Just paint a thin layer of the glue on the crack or damage and wait for it to dry — it takes about 90 seconds. Then, you can light up or relight.
Briley has over 16 years in the publishing and content marketing business. He's been writing about cigars for nearly half that in various forms. What makes him a tour de force is he also smokes them.
Source: Briley Kenney / The BS Lounge
Source: Briley Kenney / The BS Lounge
Source: Rendy Novantino / Unsplash
Source: Briley Kenney / The BS Lounge
Source: Briley Kenney / The BS Lounge
Source: Briley Kenney / The BS Lounge
Source: Mohd Jon Ramlan / Unsplash
Source: Charles Etoroma / Unsplash
Source: Ionela Mat / Unsplash
Source: Alek Olson / Unsplash
