The Gentleman’s Guide to Smoking a Fine Cigar

July 30, 2018

Some of the most talented and renowned gentlemen in the world enjoyed a lifelong relationship with their cigars. So much so, the enduring image of these men still features a cigar hanging from their mouth.

Sir Winston Churchill, Groucho Marx, John F. Kennedy and Babe Ruth knew how to smoke a cigar with style and panache — and they did it with an effortless elegance. In fact, legendary British Prime Minister Churchill has inspired many cigars over the years that bear both his name and his image, including the Davidoff Winston Churchill.

By brushing up on the basics and practicing regularly, you can smoke a fine cigar like these exceptional gentlemen once did.

Buy the Right Cigar

The process starts with the right purchase. A great smoking experience requires a quality cigar, so you need to know what to look for. Of course, you can buy one of the world’s most respected brands with a degree of confidence. These include the likes of JR, Montecristo and Romeo y Julieta (a particular favorite of Winston Churchill’s).

However, you need to know that the cigars you’re buying have been well looked after. Buy your cigars from specialist tobacconists — who know how to store and care for them properly.

Start When You’re Alone and Relaxed

The famous people in history renowned for their cigar smoking made it look effortless. Their cigars looked like a permanent appendage, and gave these formidable men a certain gravitas. But they perfected the art of smoking cigars over many years — usually in private.

Take your more comfortable seat, and try to block out the rest of the world for a few minutes. Pick up your cigar, and inspect it for imperfections. Once you’re happy you have a quality product in your hand, smell it. A great cigar has an unmistakable scent. If yours hasn’t, there’s probably something wrong with it.

Cut Your Cigar

Every gentleman cigar smoker has his own cutter. Some receive their cutter from their father or grandfather, while others have an extensive collection. Choose a cutter that looks stylish, and gets used to keeping it on your person at all times.

Most cigar smokers now use a simple guillotine cutter, which is effective and inexpensive. Exactly how much you need to cut off depends on the cigar. You need to remove enough to get a good draw, but remove too much and the cigar will fall apart. Cutting perfectly and in various environments takes practice. But the easiest way is usually to use the edge of a table — with the cutting end of the cutting hanging over it. Insert the end of the cigar into the cutting hole, and slice it off.

Lighting a Cigar

Try not to use cheap cigarette lighters to light your cigars. Not only do they spoil the image you’re trying to create, the fluid used in them can affect the flavor of the cigar. Always use a match or a butane torch lighter to light your cigar.

Lighting a cigar while it’s perched in your mouth can look sophisticated and effortless, but some smokers believe it makes the cigar too hot. Hold your cigar a foot or so away from your body, and light it as evenly as you can.


The more you smoke cigars, the more you’ll feel comfortable with them. You’ll eventually develop your own smoking style. You might, for example, prefer to smoke cigars with your favorite whiskey. Or you may prefer an after-dinner cigar with coffee.

The only thing you need to remember is not to inhale like you would with a cigarette. Take your time with it, and don’t feel you have to get your money’s worth before it burns out. Cigars are designed to burn slowly, so savor the experience and smoke at your own pace.

Finally, don’t crush your cigar like a cheap cigarette when you’re finished with it. Lay it on your ashtray, and it will slowly burn out on its own.

Over time, you will naturally develop your own style and routine. As long as you have quality cigars


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