How to Properly Smoke and Enjoy a Fine Cigar

For the past 26 years, I’ve gained much pleasure in smoking quality cigars. Firing one up sounds simple, yet there are a few things to know about how to properly smoke and enjoy a fine cigar.

Recently, I discovered a fantastic southern cigar shop, Spring Street Cigars, with locations in Tupelo and Oxford, Mississippi. I sat down with John Higgins, Spring Street’s owner, and  Mo Daher, the general manager, for a brief tutorial on the best methods to cut, light and maintain a cigar for maximum enjoyment.

Keep in mind that opinions vary widely on this topic, especially among aficionados, so in essence, there is no right or wrong way to prepare and smoke fine cigars. Yet, there are ways to maximize the enjoyment of a cigar.

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Choosing a Cigar

When you’re standing in a humidor of a specialty cigar shop, seeing hundreds of cigars priced from around $5.00 to a hefty $500.00 can be overwhelming. Today, the average price of a good cigar ranges between $8.00 to 14.00, so maximizing your experience is essential. Fine cigars are always kept in humidor rooms where the temperature and humidity are controlled. Maintaining the proper moisture content is vital to both the flavor and smokability of the cigar.

Cigars come in a variety of shapes and sizes, so I highly recommend you let a trained professional recommend one for you.

The bottom line is there isn’t a definitive way to select the right cigar for your taste. Like beer, wine, bourbon, or any other type of food or beverage, it depends on your preference. Cigars will range from mild to intense, If you’re a beginner or novice cigar smoker, I recommend you start on the mild side. Visiting a specialty cigar shop such as Spring Street is the best place for advice on selecting and smoking cigars. Davidoff is one of the more popular brands, so this Grand Cru is a smart choice. I chose Crowned Heads Las Calaveras, which retails for $11.99.

Cigar Preparation

Cutting the Cigar

Fine cigars are individually hand-rolled, so we’re not talking about the ready-to-smoke versions you find behind a convenience store counter. In fact, Mo told me that, on average, about 200 hands will touch a cigar before it is purchased and smoked.

The first step to smoking a fine, hand-rolled cigar is to cut or clip a small portion of the wrapped end so you can draw, or inhale the favor. If you look closely at the round tip, you’ll notice it is “capped” or wrapped separately. On the cap, you’ll find three small lines. You don’t want to cut below the bottom or last line. If the entire cap is cut off, then the main piece of tobacco the cigar is wrapped in will tend to unravel. However, a cigar remains smokable without the cap.

There are a few ways to cut a cigar, and I prefer a traditional, guillotine-style cutter with two blades, which provides an even cut. You don’t want to cut off the entire cap, so imagine “scalping” it, or cut off about a quarter inch. This will give you a nice, even cut. If, for some reason, you get overzealous or mistakenly cut past the cap, don’t worry because you can still smoke the cigar.

Whatever you do, don’t attempt to bite off the end. If some type of cutter isn’t accessible, you can take a small pocket knife and gently cut an “X” on the end. This will allow you to inhale and smoke a cigar properly.

Lighting the Cigar

Lighting a cigarette is quick and easy. Cigars are different. A fine cigar has several full layers of tobacco under the outside leaf, so it will take longer to light. Some cigars, like the one I’m smoking today, have bands at the top and bottom. Be sure to remove the band at the bottom, or it will impede how the cigar burns.

Here’s something new I learned. Mo advised me that before lighting a cigar I should take a “cold draw,” which is inhaling the cigar before it’s lit. This allows you to savor the cigar’s notes or flavor; similar to smelling a glass of wine or bourbon before drinking. These “notes” will be different than what you will taste once the cigar is burning. It also gives you an indication of how the cigar will draw, providing you an indication if you need to clip more off the end.

There are several ways to light a cigar. Sometimes matches or a Bic lighter are all that’s available. Both are fine and will get the job done. However, a torch lighter is best. 

First, hold the tip of the flame directly in front of the cigar without getting too close. Mo compared the process to roasting a marshmallow. If you place it directly on the flame, it will catch fire and burn too quickly, which impacts the taste. But if you place it just over the flame, you’ll get that nice brown color on the marshmallow, providing a better taste. At this point, you’re “toasting” the end of the cigar without drawing on the end.

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Now comes the fun part. Place the tip of the cigar to your lips and briefly inhale while rolling the cigar around the flame. Or, you can move the lighter or matches around the end of the cigar, helping the wrapper burn evenly.

Sometimes after initially lighting the cigar, I will blow on the end. I have no idea where I picked up this habit, so I asked Mo if that was okay.  He said it really doesn’t matter, because whether you are drawing or inhaling on the cigar or blowing on the end, you’re still providing air or combustion, for the flame.

Tip: If you are using matches, allow them to burn for a second to eliminate any sulfur they might contain. If matches are your only option, longer ones are best.

The most important part of property lighting a cigar is to make sure the outside wrapper is burning evenly. Use your lighter or matches as needed to get the cigar burning evenly.

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Enjoying Your Cigar and Keeping It Lit

After the cigar is properly lit, smoke it for a few minutes to allow the inside tobacco to burn. While there’s no set speed in which to smoke a cigar, try not to smoke it too fast. Mo advises puffing on it every 30 to 60 seconds to keep the combustion process going. I tend to smoke more quickly, so I’m trying to follow Mo’s advice and wait at least 30 seconds between puffs.

If you smoke a cigar too fast, it will tend to burn hot and impact the taste and flavor. Remember, there are many preferences for smoking cigars, and some smokers enjoy the taste of a quick-burning cigar. Mo recounted he smoked cigars faster when he first began than he does now.

Think of it this way; if someone poured you a glass of Pappy Van Winkle bourbon, would you shoot it at once or take smaller sips to maximize the flavor and enjoyment?

Here’s another tip. Take a smaller puff followed by an extended draw. Then blow a small portion of the smoke out of your mouth, rolling the remainder around your mouth to taste the notes and flavor. Unlike cigarettes, cigars are not meant to be inhaled, although everyone will inhale at least some smoke.

Dumping the Ash

At some point, you will need to dispose of the excess ash. Again, we’re dealing with a cigar and not a cigarette, so avoid “flicking” the ash off by thumping the end with your fingers.

Mo’s advice is not to dump the ash until it’s about a half-inch long. It’s preferable to have some ash because it allows the cigar to burn cooler since there’s no direct airflow at the end. Finer cigars will hold the ash longer since they are constructed of longer leaves, as opposed to chopped-up or smaller filler pieces found in cheaper versions.

When dumping the ash, gently press or roll it around the edge of the ashtray. Avoid pressing too hard, so some of the ash remains intact. If you find the ash isn’t falling off quickly, then wait a bit longer and try again. Remember, the better the cigar, the longer the ash will remain intact.

How Long Should You Smoke Your Cigar?

My personal preference is to smoke a cigar until I can no longer comfortably hold it in my hand. Cigars will produce more tar or bitterness as it gets shorter. Some smokers don’t like the bitter taste. I do.

Like fine wines or bourbons, a cigar’s aromas and charter will change as it’s smoked. John, Spring Street’s owner, will generally stop smoking his cigar after 60 or 70 percent is burned. Again, it’s all about personal preference.

If you want to minimize the bitterness or tar taste as you smoke, then gently tap the end of the cigar at some point and relight. 

Extinguishing Your Cigar

When you’ve completed smoking your cigar, don’t crush the end at the bottom of the ashtray or against another flat surface. Crushing a cigar can produce a massive smoke cloud and add unwanted odors to a room. 

Simply lay the cigar on its side in the ashtray, and it will eventually extinguish itself.

Can You Relight and Smoke a Cigar That’s Been Sitting Around

Yes, and maybe not, is the short answer. If you had to attend to guests or other pressing matters that required you to walk away from your cigar, you could relight and smoke it if too much time has not elapsed. How long is too long? Mo says coming back to cigar a half-hour or hour after it has extinguished itself is fine. However, restarting one that has been sitting around for more extended periods or overnight isn’t recommended.

Find and Visit a Quality Tobacco Shop

If smoking and enjoying cigars are of interest, I highly recommend finding a quality tobacco shop. Ask for the manager or someone experienced in the art of smoking and enjoying fine cigars. They’ll be more than happy to introduce you to the cigar experience. The fundamental knowledge you’ll gain from someone with Mo’s expertise will increase the likelihood that you’ll enjoy your first of many excellent cigars. 

Spring Street Cigars

Spring Street has five locations. Their main store is located in downtown Tupelo, Mississippi, and has one of the largest humidors you will find anywhere. Ask for Mo or the store manager, Katrina.

The second store is just off the square in Oxford, Mississippi, right next to The Chancellor’s House hotel. Ask for Todd or “Bowtie Teddy.” They’ll take excellent care of you. Recent locations are in Booneville, Starkville, and Southaven, Mississippi.