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Cigar 101


Table of Contents

1. Intro

2. History

3. Anatomy of a Cigar

4. Choosing your Smoke

5. Cutting

6. Lighting your Cigar

7. How to Smoke

8. Etiquette

9. Humidor

10. Resuscitating your Cigar



Welcome to Cigars 101. This article is meant for beginners and seasoned cigar vets alike and it’s my goal to let this be the beginning of conversation about cigars and the culture that surrounds the love of smoking. I want this to be easily digestible; something that you can read effortlessly and comprehend. Smoking cigars for the first time in public can be intimidating, but that shouldn’t be the case. Knowledge is the key to confidence, and this will give you basic knowledge.

I’d consider myself to be a relatively new cigar smoker as I have only been smoking consistently for 3 years. My passion for cigars has grown exponentially over that time and I feel like I am back in school, minus the buckteeth and zero game. How was I supposed to know that chicks didn’t dig Trek?

I digress.

The first time I smoked a stick with the boys, I unknowingly violated about 38 unwritten rules of cigar etiquette. I had no way of knowing what I was doing wrong. I was treating the cigar like a cigarette, which led to a burning canoe and me looking like a noob. I had never really been around cigars and the cigar culture that are so inextricably entwined.

Now that I am about 500 cigars into my journey, I have picked up a thing or two; things I wish I knew when I started smoking. This piece is different from anything else on SOTR, because I consider this to be a living document. I’m sure that I have left out certain things that will drive you crazy. Be gentle. But also feel free to let me know what you think. If you believe I am wrong, right or crazy, @jeremyaellis is my Twitter handle. Tweet me and give me your two cents, especially if you think I’m right! I will continue to add, subtract and revise this as my knowledge and passion for cigars grow. Enjoy.



Christopher Columbus is credited with bringing tobacco back to Europe from the Americas. Two of his sailors rolled and smoked a rudimentary cigar that they saw the natives making, and there you have it. Natives started it and Columbus brought it back to Europe where it became popular. Anyone who tries to tell you more may or may not be right, but is most certainly a douche.



Primary Growing Regions for Cigar Tobacco

Dominican Republic
United States
Cameroon, Africa

I have an affinity for Nicaraguan tobacco. I put it right up there with Cuban tobacco. I’ve been fortunate enough to smoke 20 Cubans or so, and while they are good, the legend of the Cuban cigar is fueled greatly by the fact that we can’t get them legally in the States.

The most expensive tobacco in the world is the Connecticut shade grown, out of… you guessed it, the US of A. Also, make sure to pay attention to the region where the tobacco in your favorite cigars is grown. I bet you will start to see a trend.


Anatomy of a Cigar


Wrapper– The tobacco leaf that typically defines the cigar. Cigars will be described by the wrapper and size. IE Maduro Toro. You will also read that the wrapper contributes anywhere from 40-70% of the flavor of the cigar. Whatever the percentage, just know that the wrapper is what you will think of when you picture a cigar in your mind’s eye. The two most popular wrappers that you will come across:

Connecticut Shade – lighter in color and on the mild end

Maduro – Dark and oily with a stronger flavor

Binder – The leaf between the Wrapper and the Filler. It holds the filler in and usually compliments the strength of the cigar. If your stogie has an uneven burn, the binder is the culprit (or you might be puffing too fast too hard. More on that later.)

Filler – Bunches of tobacco leaves that make up the bulk of the cigar. Two things you need to know about filler:

Length – Long and short. Premium cigars are long filler leaf and are almost always hand rolled (explains the price). The leaves are whole, and go from Cap to Foot. Short filler is used for machine rolled cigars that tend to be of lower quality. Every experience I have had with short filler has been negative. The taste just isn’t there. Long filler is like Five Guys while short filler is like White Castle.



Sunlight – Sunlight plays a major role in how tobacco develops, especially in regards to flavor. Less sun means weaker flavor, while more sun means more boom (you will see there are shade and sun grown cigars).  Here is a diagram of the filler classifications. Strongest is Ligero, weakest is Volado.


Size – The size of a cigar is measured by two dimensions: its ring gauge (its diameter in sixty-fourths of an inch) and its length (in inches).




Nuts and Bolts – The cap is the top of the cigar, while the foot is the bottom (no BLEEP, Sherlock). Then we have the body and the band.



Choosing your smoke

Ok. We’ve covered the History and Anatomy of the cigar, let’s get into the good stuff. So you are ready to go, you decide to go to your local B&M (Brick and Mortar) and venture into their humidor. With anywhere from tens to hundreds of cigars to choose from, which one do you pick? I speak from experience when I say there is nothing worse than trying a new smoke and hating it. Especially when you know you could have spent that money on a cigar you have previously tried and already know you enjoy. A cigar that feels like an old friend, or like a warm blanket on a cold night. Conversely, finding a new cigar that you love brings a great feeling. You get to add a new smoke to your repertoire!

An easy way to choose is to read a review on a smoke from a trusted source like Stogies on the Rocks, and then go find it and smoke it. BTW, we aren’t the only ones who write a good cigar review. There are some other sites that do great work as well. I just know the guys who review for SOTR and can vouch for their passion and palate.

If you want to be adventurous, go into your B&M flying blind. But, before you go, ask yourself these questions:

How long do I want this cigar to last? – The cigar size directly affects the length of the smoke. A Robusto will take you a half an hour to finish, while a Gran Corona will take you over two hours. Use our chart above to match the size with the time you want to spend.

What type of cigar am I in the mood for? – Do you want a mild smoke, or a bold one? One of the biggest factors in my decision is time of day. If I am smoking during the day, maybe on a lunch break, I tend to go for the milder smoke. After work, with a  drink in hand, I almost always go big. If I know I am going to smoke two or more in a row, I will start mild and work my way up. Generally, the lighter the wrapper color, the lighter the smoke. The darker wrappers will produce more flavor. Cigars are classified just like wine: Full, Medium, Mild.

My favorite cigars in each category:


Headley Grange

Liga Privada T52

Oliva V Belicoso


Four Kicks

La Duena

1502 Emerald


Perdomo 10th Anny Champagne

Emilio AF Suave

Now that you have an idea of what you want, head into your B&M. This is probably a good time to mention that you should become pals with the guys who work at the cigar shop. The shop is probably getting in new inventory frequently, and it’s always great when your buddy at the shop gets to know your palate and recommends a new cigar for you as soon as you walk in the door. Also, most of the guys I have met that work in cigar shops know their craft. If you go in with the flavor you are looking for and the general size you want, they will usually pick out a winner.

Go into the humidor, and find the cigar you want to enjoy. Always, and I mean always, do a quick test of the exact cigar you have chosen. It’s not difficult, but it is necessary as there is always the chance of a bum stick. What to do:

1. Gently squeeze up and down the cigar. You are feeling for hard or soft spots. If you find a bad spot, put it down and grab another. It will greatly affect your draw. It could be plugged, or it could canoe. All around bad things.

2. Glance at the wrapper. Make sure it has been properly stored and there are not cracks or torn spots. Also, you generally don’t want huge veins in the wrapper. It can hurt the even burn and is considered to be inferior.

3. Take a look at the foot. Just make sure that there is a nice tight, even pack. Stems are a bad sign.

Time to choose where to smoke! I love smoking outdoors, but if it’s windy out, it can hurt your cigar experience. The wind can cause an uneven burn, and can also over heat the cigar. That’s why God created cigar lounges. Rain, shine, tornado or snow storm, the lounge is always there for you.



I am going to get some flak for this, but cutting isn’t that complicated.

You can do the single guillotine, double guillotine, or cigar scissors for a clean cut.



You can do a V cut. I generally use this to make an X.



You can also do a punch.


Try them out and see what works. As long as the draw is solid, the cut has done it’s job.


Lighting your cigar

How you light your cigar is very important. You can ruin your cigar by lighting it with a Bic or Zippo. The lighter fluid puts off a taste that will contaminate your cigar and give off a flavor you can’t shake. The best way is either cigar matches or butane torch. Neither will affect the flavor at all.

You want to give your cigar a great start. Toasting the foot of the cigar is a surefire way to ensure an even, steady burn. When you fire up the matches or torch, keep the flame at a safe distance and move the cigar to the flame slowly, always rotating to keep the toasting even.

Once the foot is toasted, I put the cigar in my mouth and gently puff as I bring the flame close. I always rotate the cigar when I am puffing to keep the burn right. It helps after the first 3-4 puffs to blow on the lit end of the cigar. Seems to spread the cherry to the unlit portion.

How to Smoke

Now that your cigar is fired up, relax and enjoy. When I was new to smoking cigars, I would smoke them like I would a cigarette. I would puff every 10 seconds or so, which lead to major burn issues. They would always canoe or tunnel, and I would have to relight multiple times. It took awhile for me to slow down, but once I did, I found that I enjoyed my cigar even more. 2 puffs a minute is a good pace, and your cigar will stay lit.

Don’t inhale the cigar smoke. The smoke is thick and quite harsh on your lungs. Keep the smoke in your mouth for a couple of seconds, and then blow it out, allowing the incredible flavor to linger on your palate.

When you get used to smoking, you can try the retrohale. To retrohale, you want to blow 60-70% of the smoke out of your mouth and then close it. Then, blow the remaining smoke out of your nose. It will take some getting used to! With any cigar, the best way to taste the spice is to retrohale. But beware, if you have a spicy one, it could be too much and make your eyes water. Have had it happen a few times. It’s worth learning though, as it brings an added dimension of flavor and spice.

Finally, don’t ash too frequently. A good ash will prevent an uneven burn. As you start to smoke more cigars, you will notice that well constructed cigars will hold a longer ash.


Your cigar is lit, and you are enjoying the rich smoke permeating your palate. Let’s not tick off your fellow cigar smokers with poor cigar manners. As good manners will represent you well in life, good cigar etiquette will serve you well with new friends around the cigar shop and give you instant cred. My top 10 (+1):

1. Make sure to light your cigar with proper cigar matches or butane lighter. Regular matches and flame from lighter fluid puts off a bad taste that will ruin your cigar.

2. Never light another person’s cigar. This may seem like a nice thing to do, but lighting a cigar is an art form and each smoker is an artist. Everyone has his or her own method as you have yours.

3. Along those lines; don’t cut another person’s cigar. This is also a personal preference, and what you like may not appeal to someone else.

4. Direct your exhaled smoke. Everyone enjoys cigar smoke, it’s why we do it. But no one enjoys a plume of smoke sneak attacking your face.

5. Please don’t dip your cigars in liquor. I realize I am going to catch hell for this, but don’t prostitute your cigar by adding cognac or bourbon to it. A good cigar should stand on it’s own. If the cigar needs liquor, don’t smoke it.

6. Holding your cigar is a matter of preference for the most part. As long as you aren’t holding it like a cigarette or joint, you should be ok.

7. If your ash is getting uncomfortably long, don’t tap it on the ashtray like you would a cig. Roll the cigar ash along the rim of the tray to gently brush excess ash off. Try to leave a layer of ash on there always, as that promotes an even burn.

8. I have been asked many times how far is too far when smoking a cigar. Let the cigar tell you. I have smoked some great sticks that get bitter towards the end. I have smoked some great sticks that have burned all the way down to the nub and never tasted like tar. You will know when it starts to turn south.

9. Take your time smoking. 1-2 puffs a minute is the intended pace and will keep your cigar even while maximizing flavor.

10. This is a recommendation for new smokers especially; bring something to drink. I love pairing cigars with a great craft beer, glass of red wine, or fine Scotch. But I don’t always want to drink alcohol when I smoke. At minimum, I will drink water. But I also enjoy a coffee or even a Coke when I am in the mood. Cigars can dry your mouth out, and if you can’t generate spit, it can ruin your experience. Better safe than sorry.

11. When you are finished with a cigar, let it burn out naturally. Don’t mash it or crush it like you would a cigarette. This is a huge no-no. If you do this, you will be announcing that you are either a rookie smoker or you have no cigar couth. Respect the cigar.


Alright, so you love cigars. You want to start collecting cigars. You need to store your cigars. A humidor is your answer. You can get an affordable humidor for a great price, and the upkeep is minimal. You need to buy a crystal gel to keep the humidity around 65-70%. I keep mine on the high side, around 74%, but that is just personal preference.  You can also buy a humidor that is electric and will keep your humidity on point digitally. Start small; say a box that will hold 50-75. That’s what I have and while it may get full from time to time, I have never needed more space.


Resuscitating your Cigar

This is something I learned recently. When I was smoking an Illusione with Siz and Frank, the last third started to give off some tar flavor. I was really enjoying the smoke, and was disappointed that the flavor was being affected. Siz asked me why I wasn’t resuscitating it, and I had no answer. I hadn’t heard of such a thing. He was also smoking an Illusione, and showed me how to do it. Put the cigar in your mouth, and get your torch in hand. Gently start to blow air out of the cigar. Light your torch and bring the flame close to the end of the cherry. As you get to the right distance, you will notice blue flames surrounding the end of your cigar. Do this for as long as your breath will allow. Let the cigar rest for a second, and then take a pull in. I noticed that the flavor was better instantly. Back to where it was before the buildup. It makes sense, because each pull of smoke is leaving deposits of burned tobacco throughout the body of your cigar. This is a great way to make sure the flavor is where it should be!

Feel free to get in touch with me here.


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