How to Smoke Cigars: A GP Primer

Speak Softly and Carry a Big Stick

The tradition of throwing on a well-tailored suit and enjoying a ten course meal with your best friends that’s topped off with a glass of single malt and a fine cigar is rarity in most male circles these days. Well, at least the cigar part — thanks to our societal epiphany on the dangers of smoking. We won’t attempt to downplay the risks and health concerns of cigars, but we do believe that when enjoyed in moderation, they’re unlikely to strip off any additional time from your life that wasn’t already squandered by other reckless actions. We’re clearly not alone, since you’ll still find cigars are enjoyed in places like private clubs, backyard decks, or on the golf course by men who truly appreciate a relaxing, well-made, smoke.

As with any hobby or subject matter though, a lack of education can prevent curious types from understanding what all the fuss is about. This primer is designed to clue you in on three critical skills you’ll need to explore the cigar world without alerting the world to your novice ways. We’re here to talk about the following:

1. How to handle yourself at the local tobacconist and not look like a complete fool.
2. How to distinguish a well-made cigar from one with poor construction, and the best part…
3. How to cut, light and smoke for maximum enjoyment.

Our primer continues after the jump.

A Trip to the Cigar Shop

Let’s say you’re the best man and you’re responsible for tracking down and choosing stogies for the bachelor party or you just want to enjoy a backyard barbeque on the 4th of July. You go to the local cigar shop and say something vaguely intelligent like, “I need some good cigars.” Any tobacconist will know that you are a novice and will either give you a brief education on what to try, steering you towards universally appreciated cigars, or he will relish the moment like a hungry used car salesman and look for smokes that don’t sell well and have a high profit margin. What you want to do is enter with confidence and mention the event for which you are buying and what you budget is. Ask for mild to medium bodied, Dominican, Nicaraguan or Honduran hand-rolled smokes with a decent sized ring gauge (between 46 and 50), which is the diameter of the cigar measured in 64ths of an inch. Essentially, what you are communicating is:

1. That although you may not remember any specific brand, you do know that mild to medium bodied cigars will appeal to a range of smokers, from novice to aficionado, with a strength that is not overpowering.

2. That you know where the best U.S. legal cigars are made.

3. That you know that ring gauge (or diameter) matters when smoking— the larger ring gauges means that the cigar burns cooler and the draw (or basically the flow of smoke) tends to be easier.


Don’t be afraid to state your price range, and don’t forget to know what the tobacco tax is in your city/state. It could be steep. Also don’t make the mistake of thinking that the cigar must be high-priced to be smoke-worthy. Just because you pay $20 for a stick doesn’t mean it’s going to outrank a 6-dollar cigar. That segues nicely into our next topic. How can you tell actually tell what’s good?

What is a Quality Cigar?

A good cigar is a hand-rolled, whole leaf filler cigar, along with the binder and wrapper. This means the cigar has no tobacco leaf “particles” in its construction, and the cigar is rolled by hand, not a machine (those can be found at your local pharmacy for next to nothing… and they are worth every penny). Their origin can be Dominican Republic, Honduran, Nicaraguan and if you’re lucky, Cuban. The first three are U.S. legal. The fourth is not, but if you happen to be traveling abroad, get your mitts on a true Havana. It is an earthy experience not to be missed.


Check 1: The color of the cigar should be fairly consistent from head (the part which meets the lips) to foot (the end you light, the hot end) with no significant discolorations. It should also be easy on the veins, nothing overly rough or bumpy in the wrapper.

Check 2: Take a look at the foot. If the tobacco filler seems fairly tight in its binding, with no pronounced holes that you can see from the foot, that’s a good sign. If you see large gaps in the filler, avoid it. It was not made with high-quality standards.

Check 3: And do not be misled by what the band (the paper ring around the cigar with the branding on it) looks like. It is marketing, after all. Just because the band is ornate doesn’t mean it’s good, and just because one is basic, doesn’t mean it’s a waste of your dough.

Check 4: Now smell the cigar. It should be pleasant and smooth, nothing acrid or harsh. Even a strong cigar should have a nice aroma.

Excellent examples of great cigar construction (for comparison purposes) are Avo, Ashton, Arturo Fuente, Davidoff or Romeo y Julieta cigars. These cigars are consistently well-made. In fact, it’s difficult to go wrong if choosing any of these of brands. But don’t be afraid to deviate from them. There are plenty of good sticks out there. An important side note: If you happen to find that your tobacconist has stored flavored cigars in the same humidor as the regular stogies, steer clear. Flavored cigars (coffee, rum, vanilla, lemon pledge) tend to impart their odors and flavors to other stogies, which is not a good thing. Good cigars have enough flavor without needing the aid of flavoring, so if you want to remain a purist, look elsewhere.

How to Cut, Light and Smoke a Cigar

Cutting a cigar properly is one of the most important steps in the cigar smoking process. If you do it incorrectly, you could ruin a good cigar. Under no circumstances should you tear off the cap with your teeth. You are not Clint Eastwood or Will Smith for you whippersnappers. Utilize a double, curved-blade guillotine cutter, as opposed to a single straight blade cutter (which can crush the cigar).

For most cigar shapes, there is a circular cap glued on at the head of the cigar which must be cut. This is the only part of the cigar which is glued (using a vegetable based glue), so if you cut below the cap line, the outside whole leaf wrapper could come unraveled as you smoke, making your cigar look like a sad tobacco explosion.


Step 1: Gently cut the very top of the cap, exposing the filler tobacco. Check the draw by putting the cigar to your drooling lips and sucking in. If there’s enough air flow, you don’t need to cut more. If it’s still a tight draw, then keep shaving off more cap with the cutter. Just stay above the cap line. Remember, like a haircut, you can always take more off, but you can’t put it back on.

Step 2: Use either a wood match or a butane lighter but not one with lighter fluid, which quite noticeably affects the taste. Take the tip of the flame and hold it near the foot of the cigar (opposite from the part you put in your mouth), without actually touching the cigar with the flame, which could burn the outside wrapper. This will lightly toast the end. Blow on the end and then put the cigar to your lips. Exhale and gently blow a puff of air out of the cigar to release any of the burnt flavor from the initial lighting step.

Step 3: Now you can light up by drawing in the smoke and lighting again briefly. This will clear the way for pure cigar taste. Try to avoid re-lighting too often during your smoke (at least while it is still hot). If you need to step away, let the cigar cool a bit and then you can re-light. Cigar smoking is all about flavor, so draw the smoke into your mouth gently, and allow it to permeate. Avoid inhaling—this is not about getting it into your lungs.

Step 4: Gently blow out and appreciate the taste. Take your time, and you will pick up distinct flavors. Depending on the stick, you could taste everything from dark chocolate, coffee, nutty, to leathery flavors, all delicious. A good Cuban cigar will be rich, lusciously smooth and pleasantly earthy but not overpowering as many have quipped. You’ll find over time, just like food and wine, you’ll be able to pick out even the subtlest of flavors.


Holding a Cigar

Learn how to hold your cigar with confidence, with the body between your index and middle finger and the head resting in the crook of your thumb (see Mr. Nicholson; right). Get comfortable with it and you’ll soon look the part, though you should probably lose the sailor hat and put on a shirt. Adding your beverage of choice can enhance the smoking experience and prevents the dreaded cotton mouth, which can lead to a bitter smoke.

Pair your cigar with your favorite wine, port, bourbon, single malt scotch or just an iced tea or coffee. It also helps to have a good meal before you light up. A full stomach helps and even enhances the experience. We just hope you don’t fire up something as sublime as a Cuban Montecristo No. 2 after a trip to the golden arches. Make it a good meal.

Our recommendation: steak.

The Final Draw

You’ll come to appreciate that moment in time with your well-made, well-cut, and well-lit hand-rolled stogie. And for Pete’s sake, don’t rush it. It’s all about relaxation. Far too many novice cigar smokers think they have to plow through smokes like they’re going out of style, only to discover that lightheadedness soon ensues. Plus, you’d be missing the whole point of smoking, which is to enjoy yourself without regard for time. Look for our next post in this series, covering humidors, the proper accessories, along with cigar aging and tobacco types. In the meantime, you’ll find me kicking back on the deck, listening to Miles Davis blow out a few notes, smoking a fat torpedo cigar without a care in the world. Maybe you should, too.

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