How to Smoke a Cigar, a Step-by-Step Guide

There are signals of cool that need no explanation. Tipping the valet with a $100 bill. Confidently ordering rare whiskey. And smoking the best cigars like it’s no big deal.

But how do you smoke a cigar if you’re giving it a try for the first time? Don’t feel intimidated. First, you need to get familiar with the process, like how to cut, light, and ash your cigar (it's like learning how to drink whiskey neat). Next, you should learn about the tools you need, like cutters, lighters, and humidors. Finally, you can pick up on the lingo, like cap, foot, wrapper, binder, and filler. Soon, you’ll be lighting up a stogie with effortless ease—starting with the best cigars for beginners, then learning the nuances to smoke a cigar like a pro.

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If you're looking for something to pair with your cigar, try one of the best Scotch whiskies or our favorite dark rums. The flavors complement each other well—especially when shared with a group of likeminded aficionados.

Now, onto the Men's Journal step-by-step guide on how to smoke a cigar properly.

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How to Smoke a Cigar

To smoke a cigar for the first time, follow these step-by-step instructions complete with comprehensive illustrations. Cigars are meant to be enjoyed, not stressed about. So even if you take a misstep, just relish the experience for what it is: your first foray into the exciting, delicious world of smoking cigars.

1. Choose Your Cigar

As a newbie, don’t break the bank here, and don’t try to show off. Go for a modestly priced stick with a middle-of-the-pack flavor, so you can get the gist of things as you’re settling into the smoke.

2. Trim the Cap

Use a cutter to trim the wrapped end of your cigar. Look for the seam, a line of wrapper around the head, or cap, of the cigar. You want to cut above that seam, which keeps the rest of the wrapper in place. Take off enough of the cap to ensure a good draw. Start small—you can always cut off a bit more if you need to.

3. Light the Cigar

It takes more flame to light a cigar than a cigarette, so using a lighter is recommended. Start by toasting the end of the cigar you didn’t cut, which is called the foot. Hold the cigar at about a 45-degree angle above the flame, rotating it around, and allowing the end to dry out, then begin to smolder. You might take a small puff or two at this stage.

If the cigar catches on fire, don’t panic; just remove the lighter until it flames out. The cigar is ready to smoke when the foot is gently smoldering. Look for an even orange glow throughout, especially when you take that first draw.

4. Smoke the Cigar

Getting this part wrong is a dead giveaway that you’ve never smoked a cigar before. The trick is to draw in your breath, and the cigar’s smoke, without actually inhaling it.

It’s easier than it sounds. Think of the difference between sipping a whiskey and shooting it. You want to take it easy, pull the smoke in gently, let it sit in your mouth for a moment, then exhale smoothly. The point is to taste the cigar, just like you would a good bourbon or red wine.

5. Ash, Re-light, and Finish the Cigar

As you smoke, ash will build up on the end of the cigar. Although a long ash can look cool, it can also hinder airflow—or fall off onto your clothes. Remove it every so often by gently rolling it along the groove of an ashtray. If it doesn’t fall off with ease, don’t force it; just keep smoking and try again in a few minutes.

If you pause too long between draws, the cigar can begin to burn out. In this case, simply light it as you did before, paying attention not to overdo it on any sections that are still ablaze.

As you smoke it down, the cigar gets shorter, and eventually your session must come to an end. Don’t stub out the cigar; just leave it in the ashtray and it will extinguish naturally.

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What to Know Before Smoking a Cigar

You should keep a few things in mind as you start your cigar journey. First, know your own taste preferences. If you tend to like dark roast coffee and barrel-proof bourbon, you might prefer a maduro. More of a flat white and single-malt Scotch guy? Try a natural first.

Scope out cigar stores in your area and get to know the staff. The best ones will answer questions and guide you to cigars that are perfectly suited to your palate and preferred smoking occasions.

If you plan to keep cigars on hand to light up on a whim, be sure you’re storing them correctly. Invest in a good humidor, and check its levels regularly. If you can’t afford a proper humidor, at least pick up a humidor bag, which will keep your cigars in good shape in the short term.

Make sure you find a comfortable place to smoke. That could very well be your own home, deck, or balcony. But you may sometimes want to smoke in company, so check out smoking bars and cigar lounges to see if they fit your vibe.

Best Cigar Smoking Tools

Cigar Cutter

A good cutter is essential for every cigar smoker. Make sure to choose one that’s sharp, and keep it clean. There are different styles of cutter, but for a beginner, the guillotine, like Zertone Cigar Cutter Guillotine, is a good choice for versatility and ease of use.

Lighter

While you could use a wood match to light your cigar, a butane lighter or torch makes it much easier. Save the tabletop version for kitting out your home smoking lounge further down the road—a pocket-size option works well for every occasion. Our pick is Zippo Butane Torch Lighter.

Ashtray

Your ashtray can be cheap or spendy, basic or over-engineered, and it can reflect any aspect of your personality. There’s a lot of choice, but it’s hard to go wrong. If you think you’ll be smoking in a breeze, a lidded version is a great option, allowing the ash to collect without blowing onto clothing. Try U.Like Relax Zone Cigar Ashtray Aluminum.

Humidor

Although it can be expensive, the humidor is an essential piece of equipment if you plan to smoke cigars regularly. It keeps your sticks in prime shape, preventing them from drying out over time, and allowing them to age safely. A good humidor can last decades, so it’s well worth the investment. Opt for one with a built-in hygrometer, like TISFA Cigar Humidor, to keep accurate track of the humidity level.

Humidor Bag

If you don’t want to pony up for a full humidor yet, you can store a few cigars in a humidor bag. They should stay in good shape for up to a year. This is also a great option if you’re traveling and want to take some smokes with you. We like Boveda Portable Humidity Resealable Bag.

Key Cigar Terms

Knowing essential cigar vocabulary will make you sound like a seasoned, expert smoker.

• Cap: The closed end of a cigar, sealed by a seam of wrapper. You cut above the seam to prepare the cigar for smoking.

• Foot: The end opposite the cap, usually open. This is the end of the cigar that you light.

• Wrapper: The tobacco leaf that makes up the outermost layer of the cigar. There are dozens of wrapper varieties, usually identified by the plant’s seed type and where it was grown.

• Binder: The middle layer of tobacco in a cigar. It encases the filler and ensures the cigar’s structural integrity.

• Filler: The tobacco in the center of the cigar. Much like a whiskey or wine, the filler is blended and matched to the binder and wrapper to create a particular taste experience for the smoker.

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Cigar Shapes and Sizes

Cigars come in all shapes and sizes. They're measured by length, in inches, and ring gauge, the diameter expressed in sixty-fourths of an inch.

Some of the most common are parejos, cigars that are straight-sided. The most popular sizes for parejos include the corona (5.5 to 6 inches and 42 to 44 ring gauge); the Churchill (7 inches and 47 ring gauge); and the robusto (4.75 to 5.5 inches and 48 to 52 ring gauge).

There are also figurados, cigars that are not straight-sided. Common figurados include pyramids, which have a tapered cap, and perfectos, which taper at both head and foot.

How to Choose the Best Cigar

The best cigar is the one you like. Obviously as a first-timer, you don’t know your taste in smokes yet. In this scenario, getting the advice of a tobacconist is crucial. Let them ask you questions about your taste in other areas and they can guide you to a good first cigar.

As you explore, try a variety of cigars, and make notes if there are ones you particularly enjoy—that’ll help you remember the style and producer, so you can try similar offerings in the future.

Once you feel comfortable knowing your preferences, choose cigars based on how you plan to enjoy them. Do you want a stick to pair with your favorite cognac? A smoke that you can enjoy casually while golfing? Maybe you’re looking for something to share to celebrate the birth of a child or another special event.

When evaluating a cigar for quality, inspect the wrapper to make sure it’s intact and shows no signs of mold. A white powdery substance, called plume, is fine—that means it’s been well-aged—but green, blue, or gray fuzz is a sure sign the cigar has gone bad.

Next, give it a good sniff. You should smell rich, well-aged tobacco. If you note anything off, like mustiness or staleness, the cigar is no longer good.

Finally, pinch the cigar gently between your thumb and forefinger. It should be neither soft nor stiff, but should have a slight give.

History of Cigar Smoking

Tobacco is a New World plant, so it’s no surprise the earliest smokers were natives of the Americas. Columbus’s ships observed Taíno people smoking on the island now called Cuba.

As Europeans adopted tobacco, they initially smoked it in pipes. The cigar began taking hold in the late 18th century, after the Revolutionary War, and became widespread in the 19th century.

Cigars were made by hand until the advent of machine-rolling in the late 19th and early 20th centuries. Today, some of the best cigars are still rolled by hand.

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