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Cigar starter guide

Cigars for starters: Gentleman’s beginner guide

Think of a stereotypical gentleman enjoying his free time. Got an image in your mind? Chances are that this imaginary gentleman is smoking a nice cigar in your mind right now. You want to look just as sophisticated as the man in your imagination? Here is a quick beginner’s guide to cigars for you.


The setting in which you smoke a cigar is important. A cigar is a way to relax and enjoy your time, possibly with a nice drink. Smoking a cigar is a kind of “ritual”. It should be something a little special, you do at a special time.

Most bigger cigars can take a while to finish so you need plenty of time so you don’t have to rush. Time to think, relax maybe have a good conversation with a friend.

The other thing is a space where you can enjoy your cigar uninterrupted. May I suggest a man cave? Your own place where you can do whatever you want.

Take your time to enjoy a cigar.
Take your time to enjoy a cigar.

Types of cigars

Before you run out to the shop, you should probably know what you can expect there. Just like beer, coffee, wine, whiskey, etc. there is a huge variety of cigars. Let’s explore some of the most common variations.


The first thing you should know is there are two different types of “insides” or filler. The outer layer of a cigar is almost always a whole tobacco leaf. The inside is not always.

The quick and simple version of the difference is this;

A long filler cigar has whole leaves of tobacco running length-wise through the cigar.

A short filler is filled with short pieces of tobacco like a cigarette.

In general, long fillers are better quality cigars while short fillers are cheaper. But as always, you can find some exceptions to the rule.

There are countless types, brands, shapes of cigars.
There are countless types, brands, shapes of cigars.


For the sake of brevity, here is an external link with most of the types of cigars you can encounter. It covers shapes, sizes and colors.

Check it out at cigar aficionado.

Smoking your first cigar

Now onto the actual smoking of your cigar. It’s not rocket science but there are some things you should know. These are “best practices” that will help you enjoy your experience. But since you are the person who has to enjoy it so if you prefer to do something else, go ahead.  

1.     Cutting

Most decent cigars, you’ll have to cut the end cap off before you can do anything else. There are a few ways to do this but the easiest is to use a dedicated cigar cutter.

You want to create a hole that’s big enough to draw air through comfortably. If you’re using a normal, straight, cutter, you want to cut somewhere before the taper of the cap stops.

For more information, check out this article on Bespokeunit.com

2.     Lighting

Once you’ve got an opening you’re happy with, it’s time to light up. This is not like lighting a cigarette. It takes some time and a different approach. Here are a few things to keep in mind.

  • Never let the cigar touch the flame. Think roasting a marshmallow. Keep the cigar above the flame without touching.
  • Rotate the cigar to distribute the heat evenly.
  • Once you’ve got a glowing ring over the end of your cigar, take your first puff.
  • After the first puff, take another look at the lit end of the cigar. You want the end to glow evenly. If it doesn’t, touch up some spots with your flame or blow on it to distribute the glowing embers evenly.
  • Try to avoid gasoline lighters and sulfur containing matches. These can add unwanted tastes to your cigar. Traditionally a strip of cedar wood is used. A butane lighter will work perfectly fine as well though and is easier to find.  

3.     Drawing

Now we get to the actual smoking of the cigar. I don’t think I have to explain how to do that but there might be some things to keep in mind.

  • Draw the smoke into your mouth with your tongue. Don’t inhale the smoke. A cigar is about taste.
  • Go slow. You don’t have to finish in 10 minutes. You don’t have to draw too often.
  • Leaving a little gap between your lips and the cigar, so you draw a bit of “normal” air in with the smoke, can enhance the taste.

4.     Ash cone

Managing the ash cone is a bit of a skill you’ll have to acquire over time. The tobacco you burn by drawing air through the cigar will turn into ash. Unlike a cigarette, this ash doesn’t fall off very easily.

It will stay attached to the end of the cigar for until it gets too heavy at which time it falls off.

 Since the ash helps cool the cigar (which is good for the taste), you want to keep the ash on there as long as possible.

You do want to get rid of it before it drops on your pants or sofa and stains it.

That’s where the skill comes in. Finding the right time to knock off the ash before it drops by itself but preventing it getting too hot.

There is no need to use force when knocking off the ash. Just a light tap should be enough. If it isn’t, leave it a little longer.

Don't knock it off
Don’t knock it off

Cigar Tools

There are some tools you should get before lighting up your first cigar. If you’re missing these you might make a mess where you don’t want to. That’s not very gentlemanly. Having the right tools also helps you from fumbling and will make your first (and later) cigar experiences go over a bit smoother, making you look more sophisticated.

Let’s take a look at the necessities;


An absolute must have is an ashtray. You’re burning something. You can’t just drop the ash on the floor or put your cigar down on the table. Since you’re being fancy by smoking a cigar, why not get a nice ashtray?

Get one that has cutouts big enough to put your cigar down in a stable manner. You don’t want it to roll away, especially once it’s lit.

Cigar cutter

While some cigars come pre-cut, most of the bigger ones come with the cap in place. Don’t try to do like you’ve seen Hannibal do on the A-team. You won’t get a nice hole and will have little pieces of tobacco going into your mouth.

It’s better to get a purpose built cutter to do it properly. Normal scissors will flatten the cigar, making it lose its shape. A sharp knife is an option that might work, it’ll take some practice to get a good straight cut though.


There are a few ways to light your cigars. $100 bills are not the best way to light your cigar, contrary to what Hollywood might make you believe. As said above, you want something that uses butane or something else that doesn’t add nasty chemical tastes to your cigar.

Humidor (storing your cigars)

Once you’re starting to build up bigger cigar collection, you might want to invest in a humidor. If you’re just trying them out and smoke them soon after you get them, you don’t have to bother with this (yet).

Cigars taste and store best when kept at a certain humidity. While you don’t have to get a huge walk-in humidor, a smaller one that keeps around 40 cigars is perfect for the occasional smoker.