Novice to Natural: How to Enjoy Your First Cigar

Ever wondered how to choose a cigar, what tools to use, or the proper way to light it? Join our own Jack Collins as he learns from experienced cigar smokers Austin Pollak and Nick Hendry in TomTom Cigars, London. Understand the basics—from ring gauges to flavor profiles—and discover how to appreciate the slow pleasure of a well-made cigar.

Video Transcript [Lightly Edited for Clarity]:

Jack: Today, we’re at TomTom Cigars at 63 Elizabeth Street in London. What better place to learn about the fundamentals of enjoying a fine cigar? I’m here with my friends Austin and Nick. Thanks for being here, guys.

Nick: Thank you for having us.

Jack: Absolutely. So, you guys know that I’m a beginner when it comes to cigars. But I’ve been around you guys quite a bit when you’ve enjoyed cigars, so I’d really like to learn today what goes into enjoying a good cigar.

Austin: Why don’t we start with maybe what we have here in front of us that we’re going to smoke, and then we can, you know, go beyond that.

Jack: Excellent.

Austin: Okay, so we have three cigars here. Give one to you and one to Nick.

Nick: Thank you.

Austin: So these are from a brand called EGM, and EGM is an online specialist retailer of Cuban cigars, but they’ve also created their own line of cigars, which is what we’re smoking today. This is one of the vitolas, or one of the formats, called Tiburones.

Cigars or tobacco can come from different countries. This is from the Dominican Republic, which is referred to as the New World—Cuba, or Cubans, being from the Old World. And this is entirely handmade, using Dominican filler, binder, and wrapper.

So, is there a difference between Cuban cigars?

Jack: So, is there a difference between Cuban cigars? I know that there’s a lot of prestige in Cuban cigars.

Nick: I think the main reason Cuban cigars are given that much prestige is the age of the tradition of making cigars in that country, and also the terrain of Cuba itself. Much like wine is affected by the soil it’s grown in, so is tobacco. It’s fairly well accepted, if not universally, that the terrain in Cuba is the best, and the tobacco they grow there is the best. But that is not to say that the tobacco in other places, like Nicaragua, Honduras, and, in this case, the Dominican Republic, is not fantastic as well.

Jack: So it’s similar to shoemaking. For instance, I know that places like England have a rich heritage of shoemaking, and people kind of frown upon shoes made in Spain or China. But the reality is there’s excellent shoemaking all over the world. So it’s similar to that?

Nick: Just because one place is the best doesn’t mean the rest are rubbish.

Austin: The way I think about a similar analogy is tailoring. Italian or English tailoring—there’s obviously high skill in both places. It just depends on what you’re looking for and what your preferences are.

Jack: So the EGM cigars are what we’ll be smoking today, and these are quite small cigars.

Austin: When you’re talking about cigar formats or lengths, there are a couple of things to consider. You have the gauge, which is like the circumference and the length. This is a 52-ring gauge, which I would say is pretty average or standard. They can get quite narrow and quite wide.

Nick: Yeah, I think these days that’s fairly common. The ring gauge is sort of between 48 to 52 and 54.

Austin: And Nick, what do they measure ring gauge in? It’s some obscure—

Nick:  It’s 64ths to an inch, for some Victorian reason, but it is still, to this day, 64ths to an inch. In the catalogs from brands, you will see inches and millimeters for the length and ring gauge in millimeters for the diameter as well. I don’t know why it’s in 64ths of an inch, but it is.

Austin: So this is like a 52. I don’t know exactly how long it is in millimeters, but this would be, I think, for a lot of cigar smokers, on the shorter side—meaning less time actually spent smoking. So this is about, I’d say, a 30- to 40-minute smoke, more like 30. But if you’re taking your time, maybe sipping a coffee or another beverage, you could extend it a bit. Sometimes, you just want something quicker, and this is maybe why you’d go for a shorter format like the Tiburones.

Jack: Interesting. Okay, understood. So it sounds like there are other formats of cigars out there as well.

Nick: Yeah. Many.

Austin: Many.

Nick: Many, many.

Jack: Do you have a preference?

Austin: I think it just depends on the occasion. Sometimes, they make cigars that are very long and skinny, and there’s something very elegant about that. But I kind of like a bigger ring gauge, a longer smoke, especially after a good heavy meal or something like that.

I just, you know, and I like the time that smoking that kind of cigar, you know, affords me during the day—just, you know, maybe an hour, hour and a half to just sort of decompress and, you know, relax. So I’m a fan of—I generally a fan of—larger cigars.

Jack: What would you say, Nick?

Nick: I would say so, yeah. I think if you’re short on time, a shorter cigar, and if you’ve got plenty of time, then a larger cigar. Yeah, and especially, as Austin says, after a big meal, a big cigar is just, and it’s a nice sort of luxurious experience.

So, what would be the first step in the process of enjoying a cigar?

Jack: Awesome. So, what would be the first step in the process of enjoying a cigar?

Austin: I always sort of visually inspect the cigar first because, like with clothing—like with good tailoring, I’ll rephrase—good cigars are entirely handmade. So, you know, there’s a lot of work and time and steps and labor that goes into making a cigar, and I think it’s nice to sort of take a moment to appreciate that. So, just looking, there are certain visual cues, you know—I look for the evenness of color of the wrapper, the actual rolling to see if it’s nice and tightly rolled, and you can see the veins in the tobacco leaf running through there. And I just like to visually inspect it before I actually start enjoying it or lighting it.

Nick: You can also use touch. If you give it a squeeze sort of along the length of it, you can feel if there’s—if there’s any points that feel a little bit too tough. It should be kind of springy, as these ones are. And that way you can tell it’s not over- or under-humidified or over- or under-filled. And then you can satisfy yourself that it’s going to draw properly; it’s going to smoke properly.

Jack: ’Cause that’s a thing to remember, isn’t it? The fact is that these are a hundred percent natural.

Nick: 100 percent natural. Yeah, there’s nothing in here but tobacco. That’s all there is. There are no preservatives, no additives, no nothing. It’s just tobacco leaves bunched, wrapped once with a binder, and then wrapped again with a nice, pretty wrapper, a little cap on top, and that’s that. This may sound a little bit simple, but obviously, the reality is a lot more complex. But basically, yeah, that’s what it is.

What telltale signs are there if you’ve got a bad cigar?

Jack: So you mentioned whether a cigar hasn’t been humidified correctly. Yeah, what sort of telltale signs are there if you’ve got a bad cigar, so to speak?

Nick: Personally, sometimes, if it’s really bad, you can smell it, which is never a good thing. If it feels damp to the touch, then it’s over-humidified, and it’s—it’s not going to be good. If it’s overly spongy when you squeeze, that probably means it’s too damp and it’s not going to perform well. The leaves are going to be too wet to burn properly, and you’re not going to enjoy it. It can be rescued—just put it in a proper humidor and leave it for a while, and it will come back to life, so to speak, but I wouldn’t smoke it that day when it feels like that.

Jack: Understood. Okay.

Austin: And conversely, if it’s not humidified enough, it will be very sort of crunchy, and it won’t have that nice, you know, springiness to it. And I mean, like Nick said, you can also re-humidify that and get it back to, you know, a better condition where it eventually will be an enjoyable smoke.

Jack: Interesting. So unlike wine or any alcohol like that, where if it goes bad, it’s kind of bad forever, it sounds like you’re able to rescue a cigar.

Nick: You can rescue a cigar that’s been poorly humidified, yeah, absolutely.

Austin: And I hate to stick with the clothing analogies, but it’s kind of like tailoring. Like if you lose weight, you can have your trousers taken in, and if you gain weight, you can have them let out. I mean, it’s sort of a similar thing. Like these are, you know, they—they have a second life. I mean, they adapt to sort of, you know, the circumstances in which you keep them. So you can always, you know, re-humidify or dehumidify.

Jack: Interesting, good to know, good to know. So we’ve inspected the cigars, and I think it’s safe to say that we’ve all got very good ones here.

Austin: Yes.

Nick: Agreed.

Jack: What’s the next step?

Austin: Let’s cut it and get ready to light it.

Is there a difference between the tools that you would use to cut cigars?

Jack: Okay. Is there a difference between the tools that you would use to cut it?

Nick: There are sort of two or three main options, I think. A straight cut, a punch cut—which I know is Austin’s preference, especially for a smaller cigar like this. Some people would also like a V cut, which would, instead of chopping the head off, cut sort of into the middle.

Jack: Okay.

Nick: Some people like that for ones that are pointed in, some people like it for all cigars. Personally, I always use a flat cut, but it’s really sort of down to personal preference. There is no right or wrong; it’s down to just how one enjoys one’s cigar.

Jack: Interesting. I was going to say, is there a benefit or a drawback to using one type of cutter over another?

Austin: I think it depends on—well, first of all, like Nick said, it’s purely preference. I think the only time maybe you start to consider which cut to use is when you let the cigar dictate a little bit. Like if it’s a very—if it has a very large ring gauge, you know, the punch that I normally use is a pretty small punch, so you wouldn’t want to use that on a cigar with a large ring gauge because you wouldn’t be able to draw effectively.

So I think a straight cutter and SV cut would be better on, you know, something like that, but you also couldn’t use a punch on a really, really, you know, small cigar either. It wouldn’t make sense that a straight cut would probably work better there. So generally, it’s a preference, but I think there are some times when the cigar actually dictates what cut would maybe be better.

Jack: Okay. So I’ve definitely seen online that there are loads of different cutters available in terms of price range, materials used, and things like that. Do you have a preference?

Nick: For— do you mean for material or for the shape of the cut?

Jack: Yes, yes. Excellent.

What cut has everybody brought today?

Nick: So, I have a straight cut from Colibri, which has been in the wars a little bit since I bought it. I bought this at the Vegas airport. It’s my only win that week. I won 30 on the slot machine in the airport and bought a cutter. It’s quite robust. It’s nice, thick steel, which gives it a sort of—allows the edge to keep nice and sharp.

It’s got a bit of weight to it so that when you push it through the cigar, it just goes cleanly through. That’s generally what I think you should look for in a cutter: nice, heavy steel, properly sharp blades. If you go too cheap, it’s gonna be too thin, and it’s gonna sort of crack and get all raggedy, and that’s gonna ruin the end of your cigar, and that’s not gonna be good.

Jack: Austin, what about you? Do you enjoy the same sort of straight cut, or do you have a different one?

Austin: I do. I mean, I do enjoy a straight cut, and I mean, I have a straight cut myself. I think it was a party favor at an event I went to. So it’s nothing special; it’s just, you know, it’s got some heft to it, and it’s sharp, and it does the job. But I prefer a punch, and this is a plastic keychain punch that I picked up at a tobacco shop in Florence, Italy.

I think it was probably a Euro or two, but it’s just what I prefer, you know. So it’s just really simple, and I just sort of like the mouthfeel and the experience of a punch. So I tend to go for something like this more of the time.

Jack: So I get the sense that from both of you guys— and I know that you enjoy cigars quite often— you don’t put too much emphasis on your tools being super high quality. It’s a case of, you know, not necessarily super high price, should I say?

Nick: That’s— yeah, the second one is it doesn’t have to— you don’t have to go super high price to get high quality. It should be high quality because the cigar is going to be high quality, so you want to match the two so that it doesn’t ruin it. But you don’t have to go super high price to find that. It’s surprising how, for a Euro, you can get a tool that’s going to work perfectly well.

What cigar cut would you suggest for a beginner?

Jack: Excellent. So you’re going to punch yours, and you’re going to straight cut. What would you suggest for me as a beginner?

Nick: I think, as a beginner, I’d go for a straight cut. Yeah. If you’d like, I could do yours for you and put you through the process. It’s a fairly simple process, actually. People often get sort of intimidated by it if they haven’t done it before, but it’s actually quite easy. You see on the top of a cigar here, there is a little line going all the way around.

Jack: Okay.

Nick: That’s where the torsador, the roller, has put a cap on to cover the end after they’ve rolled it. We want to cut north of that line so that we don’t unravel the wrapper leaf.

Jack: Oh, well, that makes sense. You don’t want your cigar falling apart.

Nick: You don’t want it falling apart as you smoke it. Yeah, exactly. So we would open our cutter, find a nice little area just north of the line, and then a nice, firm cut slices it right off. And then that can just be deposited in the ashtray there.

Jack: Excellent. Definitely not your first rodeo.

Nick: You can see there that that’s nice and smooth off the top. You’ve got just enough that you’re going to get the smoke coming through but not so much that it’s going to fall apart. And then we would take our lighter.

Jack: Beautiful lighter.

Nick: Thank you. Thank you. This was a gift from my fiancée. I prefer a soft flame in a sort of lovely enclosed environment like this. When you’re not outside, and you can use a soft flame, I always prefer to do so. Jet flame is also an option if you are outside. If you’ve got wind to worry about, then it’s much more practical than using one of these. But since we have the luxury of smoking inside, we shall use a soft flame. You want to hold it just a little above the tip. You can see where the tip of the flame is with your eyes. The heat is actually about a centimeter above that.

Jack: Okay.

Nick: So you want to just hold a little bit above that and sort of gently roll it around in your fingers, toasting the tobacco as you go.

Jack: Is that the technical name for this part of the process? Toasting?

Nick: Toasting, yeah. Toasting.

Jack: Reminds me of that episode of Mad Men— “It’s toasted.”

Austin: And this is a step that a lot of, I think, beginner cigar smokers don’t do; that is really important to achieve a good smoke and even burn because this you’re sort of pre-lighting it, and that’s going to ensure that you don’t have, you know, some hot spots and some cold spots. You’re evenly toasting the end.

Nick: And then as we get to about this stage, where we can see it’s all nice and toasted because this is for you and not for me, I’m going to just sort of gently waft it through the air. This is just to get a little bit more air going through it so that, for hygiene reasons, I’m not putting my mouth toward your cigar.

Jack: Well, I mean, we’re friends, but I agree.

Nick: We’re friends, but we’re not that close, yeah. And then I would give it to you, and you’re ready to take a little puff.

Jack: Thank you.

Nick: And if you need to, you can always top it off with this lovely sort of table flame lighter. Other than that, it should be ready for you to enjoy.

So, what am I looking for when I take the first draw? Am I looking to take it into the lungs, or?

Jack: Excellent. So, what am I looking for when I take the first draw? Am I looking to take it into the lungs, or?

Nick: No, never into the lungs, just into the mouth. Let it roll over your palate, so let the smoke sort of coat your tongue and the roof of your mouth so that you can begin to pick out flavors. And then, when you’re ready, just pull it back out again. That’s it. Nice and simple. I think we’ll give you just a little bit more flame. If you take a puff, you take a puff, and I will just finish that off there.

Austin: Beautiful. I think when you light it and you’ve taken the first puff or two, you’re sort of—you’re—there are a couple of things you’re assessing. I mean, you’re looking to assess the quality of the draw, you know, if it’s too tight and you’re not getting enough air through, and therefore enough smoke; if it’s very loose and you’re getting a lot of smoke.

You know, I also look for the quality of the smoke. I happen to like a really sort of creamy, thick smoke, and I always find that that’s the case with the EGM cigars. So, you know, these—I sort of prefer them for everyday smokes for that reason. But yeah, I think those, you know, the three things are what I generally look for after I’ve lit it.

Jack: Interesting, awesome. So, we take the smoke into the mouth, and it’s—it’s—already it feels like it’s similar to appreciating, like, a whiskey or a fine spirit, where it’s about the taste and the experience, rather than a nicotine hit or something like that.

Nick: Agreed.

Jack: With that in mind, are there any health concerns with smoking a cigar? Because I know that, obviously, smoking is becoming slightly less prevalent in certain parts of the world. Would you consider that enjoying a cigar occasionally is like enjoying a drink occasionally, perhaps?

Austin: I think everything in moderation—I don’t know. I have a family member who’s an ER doctor, and he likes to smoke cigars. I asked him this exact question, and he said, you know, a cigar every, you know, a cigar every once in a while or on occasion is not gonna really hurt you, but I think, you know, people—it just, it depends. I mean, if this is your one vice, you know, and you’re not a big drinker, you’re not doing, you know, other things.

I think it’s totally fine. And, you know, if this is what you enjoy and it brings you happiness, you know, I think, in my opinion, go for it. I mean, I always sort of think about the health implications, too, but I also, you know, I try to save cigars maybe for more special occasions or moments, you know, not just sort of smoking mindlessly.

Jack: Mm-hmm, that’s understandable.

Nick: Yeah. Yeah, the same for me. There’s—there was actually a study done recently, funded by the FDA into premium cigar smoking, and it found that, because of the frequency of, of enjoyment of premium cigars, it’s not as much of a health issue as other forms of smoking. Yes, tobacco smoke does have bad things in it.

We all know that, and there’s no getting away from that. But what that study said was that if you’re doing one to two per week, as Austin just alluded to—and that’s certainly what I do, it’s certainly what a lot of people do, premium cigar smokers do—their finding was that that presents no significant increase in risk.

At that frequency, if you’re smoking three a day, then obviously, then that’s, you know, with more smoking comes more risk. One or two a week as a special occasion, according to them, is no real—no real—problem.

How often should you take a draw from a cigar?

Jack: Good to know. Okay. So, how often should you take a draw from a cigar?

Austin: I don’t know if there’s a hard and fast rule. I—I had someone once told me that about a puff a minute is like a good rule of thumb. I mean, I think I probably, on average, take more frequent puffs, but I think a puff a minute will sort of then ensure that your cigar won’t go out on you. But there really aren’t any rules. I think it’s just personal preference with cigars.

I mean, you know, you should—sure, there are maybe, you know, customs or norms, but at the end of the day, it’s about your enjoyment of the cigar, your enjoyment of the experience. I think you should just do whatever you enjoy.

Jack: That makes sense. Is there anything I’m looking for when enjoying the cigar? So, for instance, I can see at the moment that I’m starting to get some ash along the tip here, but it’s not necessarily even. Is that a normal experience?

Nick: It can be. Again, you could just top up the side of the cigar, which is not burning fully with your lighter. This will occasionally happen with cigars. Sometimes, the person who lit your cigar for you didn’t do it properly.

Jack: There’s no judgment here, you know.

Austin: I don’t know if this is true or not, but I had someone tell me this once, too. Like on my cigar, the way I’m holding it, the top is not burning properly. And if you sort of hold it with that up and then you take a couple of draws, it’ll sort of even itself out. So you can kind of self-maintain.

Nick: I’ve actually been told the opposite.

Austin: Oh really?

Nick: Yeah, which is weird because heat rises, right? So your way should be proper. But when it was explained to me by a gentleman who’s a cigar professional—he knows more about cigars than I ever will and than most people in the city—and he said, it is counterintuitive, heat should rise, but apparently if you put the non-burning side on the bottom and take a couple of puffs, then it will right itself. The science behind it is beyond me. He told me to do it, so I do it because I trust him.

Austin: Well, let’s give it a go.

To enjoy the cigar, is it about just slowing down and appreciating the taste of the smoke?

Jack: Absolutely. So, as you’re enjoying the cigar, is it about sort of just slowing down and appreciating the taste of the smoke?

Austin: I’ll be honest with you. I am not so great at picking up cigar flavors. I mean, I know people that sit there with a journal and write down all the different flavors and things that they pick up on their palate. I mean, I just get a lot of your typical sort of flavors when I smoke, but I try not to pay attention to that because I think that’s sort of, you know, single-minded, or, you know, then you just focus on that. So I just look for, you know, overall pleasurable taste.

Jack: There’s a slight sort of spicy, woody sort of quality.

Austin: Almondy. I mean, it depends also on, you know, on the tobacco that’s used.

Nick: It will depend on the tobacco and the way—the ratios in which it’s been blended by the blender who’s put together the recipe, if you will, and also where it’s from. Like, Nicaraguan cigars would tend to be a lot spicier because of its volcanic soil. Yeah. And, you know, you can blend stronger leaves with more mild leaves, and that’s going to have an effect on it as well.

Austin’s perfectly correct. There are a few regular flavors that you get, I think, from cigars. It’s not like wine, where there’s a big list of hundreds of summer fruits and all this sort of stuff you can get from it. There are a few classics, one of which is tobacco—it tastes like nicely roasted tobacco. But yeah, nuts and almonds and sometimes like black coffee and that sort of thing.

Austin: I think like black pepper, and sometimes you get spiciness. Like we were talking about before, this is a smaller cigar format, and I think the flavors are a little bit more condensed. So, I mean, I would say this is a medium-bodied cigar, and, you know, I tend to get a little bit more spiciness from this cigar versus other EGM cigars. And I guess while we’re talking about that, we can talk about generally how flavor develops in cigars, right?

So, cigars are broken down into thirds. You have the first third, the second third, and the last third. And as you’re smoking, you’re drawing in the heat; the flavors are going to develop. So what starts as a nice mild cigar towards the end, you might pick up entirely different flavors, and also it might get much stronger. Just like Nick was saying, it depends on, you know, how the person who rolled it, how they’ve blended the tobacco.

Jack: So, is that thirds in terms of literally?

Nick: Thirds of the length.

What’s the etiquette for ashing your cigar?

Jack: So, as the ash starts to form and the cigar is burned, what’s the etiquette for ashing your cigar?

Nick: You should just, when you feel it’s time for the ash to be removed from the edge, just put it to the ashtray and gently roll it off. There’s no need to be overly aggressive or forceful with it. It will generally stay on for quite a long time.

Jack: Oh, really?

Nick: Yeah, it would. It could have lasted far longer than that, I’m sure. And that’s a sign of good construction. When it’s been well made, and they’ve used good tobacco, it will hold together surprisingly well. What you don’t want is for it to fall on your clothes. I generally find roughly a centimeter, every centimeter or so, or every half inch or so; I’ll do that just to make sure it doesn’t fall on my clothes. There are people who enjoy making the longest hunk of ash they can on the cigar. There are actually competitions devoted to it.

Jack: Oh, really?

Nick: Yep. But to me, it involves too much that you end up smoking like this—like, really, really carefully. And to me, that—I’m not enjoying that anymore. I’m worried too much about not removing the ash and not worried enough about just sitting back and enjoying the cigar. If that’s for you, then that’s for you, but it’s not me.

Austin: You see people laying down horizontally with just a cigar pointed up and, you know, you know where the ash is going to end up. It’s just a matter of time. But I, I mean, I’m notorious for, like, always getting ash on myself, but that’s because I find that when you ash, it actually changes the dynamic of the smoke and the flavor a little bit.

I think the longer ash you have, the cooler the smoke is, and the less, like, forceful, maybe, the flavor. So, I like to sort of take the ash down until I get to a point where I start worrying it’s going to fall, at which point I’ll ash it because when you do ash it and then take another draw, I mean, I think it’s a little hotter, spicier.

Nick: That’s right.

Austin: Yeah, so there’s, you know, it’s a flavor thing as well.

If the ash does get on your clothes, is there anything that you need to be aware of or do to ensure you don’t get stains?

Jack: So you mentioned if the ash does get on your clothes, is there anything that you need to be aware of or do to ensure you don’t get stains? I’ve probably not worn the right color suit for this.

Nick: You’d be surprised. I’ve ashed on lighter color suits than that. Oh yeah, yeah. The one thing I would always say is remember to look—I’ve got some ash on me right now—brush, don’t rub.

Jack: Okay.

Nick: And then it’ll just float off.

Austin: And you can even sort of, like, you know, flick it, which I find works.

Jack: Okay.

Austin: But yeah, like Nick said, you do not want to rub it in.

Nick: Don’t massage.

Austin: Yeah, then that’s kind of there.

Jack: So, as the smoke continues, I see that the band is here. I’ve heard that the band is the stopping point; is that true?

Nick: I mean, not for me. I like to enjoy more of the cigar. It can be if you want it to be, but the band is really so you can tell whose cigar you’re smoking and from which brand it is.

Jack: Oh, I see, this is just advertising.

Nick: This is just decoration.

Jack: Yeah.

Nick: Many people would probably stop around an inch from the end. Some people would put a little spear into the side of it so they could smoke every last bit. Personally, I’m an inch-from-the-end kind of person. But when you feel, when you see the cigar getting to around this sort of stage, you can just remove the next band in sequence and put it in your pocket. Some people like to save them.

Jack: Okay, so almost like a catalog of cigars that they’ve smoked. Some people make—

Nick: Yeah, some people have, like, little notebooks. Some people make collages of artwork and things like that. Some people, like me, just throw them in a bin.

Austin: And really, especially cigars, I like to sort of write on the back, you know, like if I’m smoking a cigar with, you know, my dad and it’s a particular, memorable cigar, you know, or an experience, you know, I just sort of like to make a note of that on the back of the band, and I stick it in, you know, a little catch-all that I have at home, just for memory’s sake.

It’s nice. You know, I’ll give it to him. It’s a little gift. But one of the—one, one—another sign of actually a well-made cigar is how easily the band sort of comes off because the bands are applied with a little bit of glue or tack, or it’s actually a little bit of gum, natural gum. And if it just sort of pulls off very cleanly and easily, that’s, you know, another sign of a well-made cigar.

Jack: I see. Okay. So, there are a few factors to look out for when judging the quality of a cigar, and it’s useful to know that the band is one of those things.

Austin: Useful but not ultimately that important because, at the end of the day, it’s more about the actual cigar. But it’s one of those little—it’s like, I don’t know, you know, pick stitching or something on a lapel. It’s a little tiny detail that maybe isn’t so relevant, but sort of, if you know, you know.

Nick: You can tell if you see that detail. If this manufacturer has paid attention to that, then the chances are they’ve paid attention to everything all the way through, and you can trust their quality.

Austin: Since we’re filming, I’m going to actually ash my cigars. I would keep going if I was at home in my garden or something, but I don’t want to be the only guy.

And that’s important—to actually take a, you know, a draw sort of right after you ash. It sort of helps to maintain, you know, an even burn. So I probably waited for a second too long here, but you want to take a draw after you ash, generally.

Jack: So when it comes to enjoying a cigar, and you’re probably going to be doing this in the company, what sort of etiquette amongst cigar smokers do you think is important for newcomers to know?

Nick: Well, I think first of all, as we discussed when I was lighting your cigar for you, the reason I waved it is because you don’t put your mouth on someone else’s cigar. People sometimes say to me, “Would you like to taste this?” and I’m like, “No, no, that’s yours, and I’ll have mine.” And that’s fine, but generally, it’s just, you know, respect. If you’re in a place like this, don’t be too loud.

Austin: Yeah.

Nick: Don’t be sort of too ostentatious or trying to—every now and again, you’ll find the guy who likes to shout about how expensive his cigar is. Shut up and enjoy it. There’s no need for that sort of thing. And yeah, just sort of acceptance of the fact that everyone has their own tastes, and it’s everyone’s hobby. You tend to find in a place like this that everyone has that common ground of loving cigars, and that will generally be your conversation, and just respect everyone’s sort of opinions on it.

Jack: Is that your experience of the cigar community that they’re quite open and accepting of newcomers?

Austin: For the most part.

Nick: Yeah.

Austin: Yeah, I mean, it’s not nice to be a snob about anything. I don’t think it’s, you know, to turn it off or put it off, but I find that in London, there’s a really rich cigar culture and community here. You know, a lot of it happens in cigar lounges like this, but also, you know, on terraces and back patios. But people tend to be very knowledgeable here, very open, and willing to share, which is lovely.

I mean, not just share knowledge, but also, you know, share cigars, trade cigars, you know, open up others to, you know, new experiences—cigars they haven’t smoked before, maybe from regions that they haven’t, you know, had cigars from. I’m from the States, and when I moved here, that was my first time with access to Cuban cigars, so that was entirely new for me and so much fun. And I’ve learned a lot just from, you know, sitting with Nick and other people in the cigar community smoking Cubans. So—

Jack: Awesome. So it looks like mine’s potentially gone out. What happens at this stage? Do you just relight it?

Nick: Yeah, it happens. It happens to everyone. If there’s a lot of ash on the end, I would clear that off first. But other than that, yeah, just pick up a light.

Jack: What would you suggest with this one?

Nick: And I would give it a little tap just to, yeah, just to sort of clear that little bit off the top. And then, and for a relight, I would tend to go with a jet flame.

Jack: So a jet flame like this, a bluer flame?

Nick: Yeah, yeah, it’s much more sort of high power coming out, so the flame goes blue, and you can be a lot more accurate with that than you can with the softer flame, seeing that that’s perfect, ready to go again.

Jack: So when it comes to enjoying cigars, do you just stay at home and enjoy them, or do you travel to enjoy cigars and enjoy smoking around the world, I suppose?

Nick: Yes! Yeah!

Jack: That wasn’t a surprise.

Nick: All of the above. Yeah, all of the above.

Austin: I think there’s nothing nicer than if you’re traveling. I always bring some cigars with me because you never know when you might find a nice environment to sit down in. Like, we were—my wife, and I were in San Sebastian a couple of weeks ago, and we were walking along the promenade, and there was a bench there right on the bay, and you know, sat there with a beautiful cigar, you know, at sunset, and it’s just—it was so perfect. So, I like to be prepared for any situation. But my favorite is just a more casual setting. Like, I love smoking in my garden or—yeah, I love smoky environments like this too; it’s just a little bit of a different experience.

Jack: So, with that in mind, do you ever run into any issues with taking your cigars with you abroad? Are there any legalities around that? What sort of issues might you run into?

Nick: Every country has its own laws and regulations on how many cigars you can bring in. Generally speaking, it doesn’t really affect personal use. I think the lowest number I’ve seen is five. If you’re going somewhere for a week, you don’t need more than five cigars. You could maybe even buy some there, but if you wanted to have, as Austin said, it’s nice to be prepared for finding that bench in San Sebastian. You can have two, three, four, or five in a little sort of travel humidor or just a leather pouch. They’re not gonna—nothing bad is going to happen to them then. I would say if you are traveling by plane, they go in the hand luggage, not the hold.

Jack: Okay.

Nick: Because you want them to remain at your temperature. You don’t want them going in the coldness of the hold.

Jack: Oh, so that can ruin the smoke.

Nick: It’s not gonna ruin it, but it’s gonna maybe take a few more days to recover them than you have in your destination.

Jack: I see.

Nick: So yeah, if— and also I don’t want to lose them. If the airline loses my bag, yeah. Yeah, I want my cigars with me. But yeah, and also, traveling with your lighter, I would have liked a really cheap throwaway gas lighter. It’s allowed in your liquids bag. Take that one with you. You should be able to take it anywhere. And if you’re not, you’ve lost a couple of dollars; it’s not the end of the world. Don’t take your good lighter.

Jack: I was gonna say, because you do have a beautiful lighter. Is it a DuPont?

Nick: It is an S. T. DuPont, yep. I do not travel with that except on the Eurostar because—

Jack: It’s the train—

Nick: Because it’s the train. So they let me, but I never, I never take it on a plane just in case. I have plenty of little gas lighters that I’ve paid four or five pounds for.

Austin: It’s like Nick said, it’s not worth risking losing a very expensive lighter for. And you can never travel with a torch lighter, like a blue flame. Technically, you can travel with a soft gas flame. You just have to make sure you empty the gas entirely, but then again, you’re sort of at the mercy of the security agent, and it’s just really—

Nick: Did they know that rule? Probably in a bad mood…

Austin: Yeah. It’s not risk—not a risk worth taking. So I just travel with the Bic, or even just buy a Bic, you know, or something similar at the destination I’m going.

Jack: Oh, that’s not a bad idea then. Yeah, so just don’t even bother with the lighter in your luggage. Buy one when you’re there.

Austin: Yeah, cutters are fine. No issue there.

Jack: Cutters are fine.

Nick: Yep.

Austin: But yeah, just be careful with your lighter.

Are matches a viable option for lighting a cigar?

Jack: What about matches? Are matches a viable option for lighting a cigar?

Nick: I think they are, yeah. I think they’re the most—well, one of the most elegant and certainly the most traditional way of lighting a cigar. Not necessarily the most practical way, but again, in an environment like this, if you have the luxury of being in a lounge, then you’re not disturbed by wind, and you can light a nice, long cigar match. Make sure you let the head burn off. So you want the little phosphorous head, you want that to burn off and wait for the wood to catch. And then you can use that to light your cigar very, very easily, and it does look good. It makes you look cool.

Jack: Does it inform the flavor?

Nick: Not really, no. It will if you light it with the phosphorous part; it could taint the flavour.

Jack: So you don’t want to just strike it and immediately—

Nick: I would—yeah, I would avoid that, yeah.

Austin: And some people claim the jet flame will burn the tobacco and create, you know, maybe an off flavor, but that’s why you sort of hold the jet flame away from the tip of the cigar, and you just sort of use the heat at the top and not just, you know, shoving the jet flame in there and lighting, you know, point-blank essentially.

Jack: So, gas lighters—what about, for instance, at home, I have a petrol lighter, you know, like lighter fuel.

Nick: Like a Zippo or something.

Do the different fuels affect the cigar smoke?

Jack: Yeah, exactly. Would that sort of thing be permissible, or would you say that the different fuel affects the smoke?

Nick: It’s widely held that the petrol will taint the flavor as well. So widely held, I’ve never tried it.

Jack: Have you?

Austin: No, I’ve not, no.

Jack: Interesting, okay. So maybe that’ll be a topic for another video. Taste testing.

Nick: Taste-testing Zippos.

Austin: We were talking about health concerns before, maybe if it’s in there, yeah.

Jack: Excellent. So, as we continue to enjoy the smoke, we’ll obviously reach a point where the cigar ends. What would you do? Do you just have a natural stopping point? Is there any indication that tells you that the smoke is over?

Nick: If you stop enjoying it, I say the smoke is over. As we were saying, for some people, that’s when they get right to the bitter end with their little spear in it. For some people, it’s when their fingers start being singed because the burn line is too close to them. Whichever you decide, when you’ve decided it’s done, put it in the ashtray. And that’s it. Don’t stub it out. Don’t—just put it in the ashtray. 

In a few seconds, it will go out on its own. And it’s sort of; it’s, I suppose, part of cigar etiquette that this has gone through a lot of different hands, from the seedling to the plant in the field, all the way up through the curers in the barn, and etcetera, etcetera, to the rollers. It’s a sort of sign of respect for their craft and dedication that you let it die with dignity. You don’t stamp it out. You just put it down and let it finish.

“It’s a sort of sign of respect for their craft and dedication that you let it die with dignity. You don’t stamp it out. You just put it down and let it finish.”

Nick Hendry

Jack: So the cigar etiquette continues all the way—

Nick: All the way to the end.

Austin: I think that’s probably actually one of the signs of a newer cigar smoker, which is how they put out a cigar. I mean, if you see them really sort of, you know, stubbing it out in the ashtray, you know, there’s again nothing really wrong with that. It’s just not the most elegant way to do it.

Nick: We’ve all done it. I did it when I first started smoking cigars, and then that was explained to me by someone else in the lounge, and I went, “Oh, you know what? Yeah, that makes sense.” And since then, I’ve followed that.

Jack: Awesome. So, how do you guys think I’m doing so far?

Nick: Like a true professional.

Jack: Because I think this is the point where I need to come clean. This isn’t my very first cigar. I actually—before we filmed, I made sure that I wasn’t a complete novice, and I enjoyed a cigar, my very first cigar, with you guys a couple of days ago. And that was a big part of me getting over the fear, any stigma, of enjoying a cigar. What was your first cigar experience like?

What was your first cigar experience like?

Austin: It was a long time ago. I mean, I think I—probably too young. I was, I don’t know, probably ten or something, but all the guys in my family smoked cigars. And, you know, when my dad and my uncles and my grandfather, you know, we all get together, it’s always around a cigar. And I think my grandfather, you know, allowed me to have a puff of his cigar too when I was probably like eight years old or something like that. My mom wasn’t too happy about that one. But, you know, I think that was my first time experiencing a cigar. I can’t say I enjoyed it or anything like that. Obviously, I was way too young, but yeah, it was a fond memory.

Jack: I was gonna say it sounds like it definitely stays with you.

Nick: Similarly, I think my—technically, my first experience of cigars, I was probably illegally young. But I would say my first experience with premium cigars was in a place not dissimilar to this, where Austin and I like to go and drink whiskey and smoke cigars. And I found myself there one evening, I was drinking a nice whisky in an armchair very similar to this one.

And one of my friends, who I’d made there, said, “Oh, why don’t you try this cigar?” He was exceptionally knowledgeable and very well prepared for the occasion. So he kindly gave me one from his humidor. And it just—the cigar he gave me was a Cuban cigar—it went really, really well with this Scotch whisky that I was drinking.

And from then on, I was like, yeah, this is the kind of— that happened to be at the end of a particularly difficult work week. And now, at the end of, frankly, easy work weeks, I still use that as an excuse to sit with a good whiskey and a good cigar.

Jack: Nick, Austin, thank you so much for sharing a cigar with me. Beautiful EGM cigar at the TomTom’s Lounge in London. It was a real pleasure.

Nick: Pleasure to be here.

Jack: Thank you.

Austin: Thank you.

Jack: Thank you.

Do you have a preferred cigar brand, a unique ritual, or a memorable smoking experience? Share your thoughts and stories in the comments below!