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A Gentleman's Guide To Cigar Smoking

I was in Scotland two summers ago, and I did a tour of the Oban scotch distillery. It was fascinating stepping into scotch and Scottish history like that. Oban has been around since 1794 and has the shining reputation that any company over 200 years old needs to stay relevant for so long. During my tour of the quaint facility, I asked the guide if there was a “right” way to drink whiskey.

“Not at all,” he replied. “The way you enjoy whiskey is your

business. Whether you drink it straight, on the rocks or shoot it back, there’s no wrong way to enjoy this drink.”

I enjoyed that answer because it took a lot of the mystique and rigid tradition out of scotch drinking and made it appealing to everyone. So often, when talking about high-quality scotch, rye and bourbon, men love to obsess over the details.

“Things must be done this way,” they’ll stress. “These whiskeys are good and those are bad.”

Whiskey connoisseurs love tradition and order but ultimately, their order is arbitrary and entirely subjective.

I mention whiskey because I believe fine spirits and cigars have a lot in common. Each are enjoyed (typically) by esteemed men with money and both hobbies have an obsessively rigid, if not authoritarian, fan base. Yet, like whiskey, the traditions surrounding the “proper” ways smoke a cigar are, more or less, a personal preference.

First and foremost, there is no right taste for a cigar.

By that I mean your taste buds will determine what you think is good or bad. That isn’t to say, however, that too much or too little humidity in a cigar won’t drastically influence its taste and make it better or worse. While I am no fan of rigidity when it comes to smoking, I do recognise many factors go into getting the most out of a cigar and that’s what I want to share with you today.

So, let’s look at the commandments of cigar smoking, shall we?


I have smoked $10 cigars that, in my opinion, taste and smoke far better than $50 cigars. This is why when someone comes in a store and asks for a good cigar, I have trouble saying, “THIS…this is the best cigar in the world. No questions asked.”

What I try to do, and what I urge you to do when you buy a cigar, is look for quality. Forget the price tag as much as possible and ask the store clerk, “What’s a cigar that sells well and is consistently a good smoke?”

When people ask me this, I generally show them anything made by My Father Cigars and the Montecristo Open series.


Hollywood and a decades-long embargo in the United States has created an incredible mystique around Cuban cigars. Are Cubans good? Sure, some are good, some aren’t. It’s like anything else. Try out the Romeo y Julieta and Montecristo and Cohiba for the same reason you try out Glenfiddich or Johnny Walker: they’re iconic brands. But you’re going to find terrific cigars for far less cost when you venture outside the country of Cuba.

Variety is the spice of life. Cigars don’t break this rule.


Cigars are meant to be drawn into your mouth, held for a brief moment and the released. This will allow you to experience the full flavour of the stick without the detrimental effects of inhaling a pack of cigarettes worth of nicotine, which is obviously horrendous for your health.

Some people like to inhale a bit of their cigar to get the head rush that comes with a hit of nicotine. After a long week of work, no one is going to blame you.


If you’re not committed to the 40 minutes and more it takes to finish a “full size” cigar, buy a cheap stick for a couple dollars or buy a cigarillo.

Putting out and relighting a cigar comes with a plethora of downsides including altering the taste of the stick. I equate relighting a cigar to drinking a can of beer that’s been left open overnight. By that I mean you can do it, but I wouldn’t recommend it.


Rule of thumb says to wait between 30 seconds and one minute between draws. You can decide what works best for the stogie you’re smoking but it’d be a shame to buy a good cigar – like a Montecristo No. 2 or a My Father Le Bijou – and smoke it like a cheap cigarette. Cigars are meant for long conversations or long stretches of quiet relaxation and they should be enjoyed at a pace that extends both those scenarios.


Enjoying a cigar begins before you’ve even chosen your stick.

The moment you walk into a cigar shop, your experience with a Cuban or Dominican or Honduran or Nicaraguan can be improved by asking questions. Generally speaking, even if the person at the shop isn’t a connoisseur, they will know what sells well at different price ranges and origins, so be vocal and pick the brains of the folks working.

As someone who works at a cigar shop, I love nothing more than a customer who comes in and asks me a handful of questions about our product. Like wine or whiskey, cigars are a premium, organic product and there is just so much to learn and share.


Yes, even though I called this guide a set of commandments, and commandments are supposed to be unwavering rules, take it all with a grain of salt.

I cannot stress enough how much more important your enjoyment is than my gentlemanly suggestions. If you like cheap cigars you can smoke like cigarettes and put out three or four times before finishing, I promise you I won’t get in your way.

…I may judge you to no end and question your path in life but dammit, I’ll defend your right to choose how to best enjoy your tobacco.

I hope you enjoyed this post. If you have any suggestions, questions or comments let me know on Twitter or Facebook.


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