If you're ready to join the ranks of cigar smokers, here is how to get started. The first step is selecting the right cigars to "practice" with. You should start by choosing several different single cigars at your local tobacconist. Do not buy a box of cigars until you have sampled a few singles, first. Don't be afraid to ask the owner or manager for advice.
Mild cigars are recommended for beginners, since the more full-flavored cigars would most likely taste too strong (or just plain bad) to a new smoker. Mild cigars are also the least expensive, so you won't have to worry about ruining an expensive cigar by lighting it incorrectly, or by cutting too much off the closed end.
Once you have determined which type of cigar(s) to purchase, then gently squeeze the cigar to determine if there are any hard or soft spots. You don't want to take a chance on buying a cigar with a bad draw, or worse yet, one that is plugged and not smokeable. Tip: Reputable tobacconists will usually replace a plugged cigar. Also, inspect the wrapper for cracks or discolorations.
If you do not yet own a humidor, do not buy more cigars than you can smoke within a couple of days, and make sure to leave them in their cellophane packaging (if applicable) until you're ready to smoke. Never leave an unprotected cigar exposed to the elements, as it will quickly dry out. You can temporarily store cigars in a Tupperware or similar container.
The closed end (or head) of a cigar is the end that you put into your mouth, but you have to cut it, first. When a cigar is hand rolled, a cap is put on the head of the cigar to keep it from unraveling and drying out. A cigar should not be cut until you are ready to smoke. There are three styles of cuts, and several types of cutters, but the straight cut made with a guillotine cutter is the most common. Hold the cigar with one hand and the guillotine with the other, then insert the head of the cigar into the guillotine and cut into the cap, usually about 1/16 to 1/8 of an inch down. If the head of the cigar is shaped like a cone, then cut into the cone, but not quite at the widest part. In any case, do not cut into the body of the cigar. That would cause the wrapper to unravel, and ruin your smoking experience.
The most primitive way of cutting the head of a cigar with absolutely no tools is to bite it with your teeth. This is a last resort, and should never be done with an expensive premium cigar, as the cigar is much more valuable than a basic cutter. Biting a cigar, or otherwise cutting it improperly, will cause the wrapper to unravel, and could even damage the binder and filler tobacco inside. If available, use a sharp knife and a cutting board, or a pair of sharp scissors. You can also use a pen or pencil to punch ahole in the cap. If the cigar costs more than $5, do not cut it until you have a cigar cutter. It will be worth the wait.
After being cut, the cigar is now ready for lighting. Butane lighters or wooden matches are recommended. It is important not to introduce chemicals or other flavors or substances into the cigar as it is being lit (never use a scented candle). There are many types of lighters on the market, but butane torch lighters work the best outdoors, especially on a breezy day.
Light your lighter with one hand, then grip your cigar around the band (or about an inch or two from the head) using your thumb, index finger, middle finger, and ring finger (if necessary), and place in your mouth. Position the end of your cigar just above the top of the flame, being careful not to let the cigar actually touch the flame. Begin puffing on the cigar, then slowly begin to rotate the cigar while continuing to puff. Depending on the size of the cigar, you may have to continue puffing while rotating the open end above the flame for at least 10 to 20 seconds (sometimes longer,) until the tobacco around the outer rim begins to glow, and the smoke begins to easily draw.
Now that your cigar is all fired up, it’s time to smoke and enjoy it. Continue to puff and rotate about every 30 to 60 seconds. Do NOT inhale the smoke, just taste it in your mouth and blow it out. If you smoke a cigar too fast, it will burn hot and ruin the flavor. If you smoke too slow, it will go out and you will have to keep relighting. Since most hand rolled cigars are made with long filler, you will not have to flick the ashes until they are at least ½ to one inch long, depending on the cigar (and any wind conditions, if you are outdoors). You can smoke a cigar as far down as you wish, depending on the taste.
Other than the taste and draw of the cigar itself, the drink chosen to accompany a cigar is the second most important factor that will affect your enjoyment of the smoking experience. If comparing different cigars, always make sure to have the same drink. Many drinks are compatible with mild cigars, but as you move up to medium and full flavored cigars, it is important to choose a drink that will not be overpowered by the flavor of the cigar. Coffee drinks, port, scotch, brandy, and most drinks made with Kahlua can accompany any cigar.
Proper cigar storage is crucial. If you do not store your cigars properly you may encounter some of the following problems: uneven or too rapid burn, harsh or bitter taste, broken wrapper, difficulty lighting or keeping the cigar lit, mold, and -oh horror of horrors!- tiny holes in your cigars, a sign of tobacco beetle infestation. You can prevent these problems by keeping your cigars below the maximum temperature of 73°F (23°C) and between 68-74% humidity. Ideal conditions are 70°F (21°C) and 70% humidity. Cigars kept outside of a humidor may last 1-2 weeks depending on your climate, but make sure that you keep them in a sealed plastic bag.
Choose a humidor that is large enough for the quantity of cigars you wish to keep and that has good construction and a tight seal. Most humidors will include a hygrometer and humidifier but you can also purchase these devices separately.
Another hazard of cigars stored in too hot or humid an environment is an infestation of worms called lacioderma. The worms lay eggs inside cigars and burrow out, forming tiny holes in the wrapper and metamorphosing into tiny, brown beetles. If you discover the presence of worm holes in your cigars, remove and destroy the affected cigars immediately, and then carefully inspect all the cigars in your humidor for signs of infestation. To check if the hygrometer is reading correctly, use the salt method to test its calibration.
Do not keep your cigars in the refrigerator as it will suck out the moisture content of your sticks. Freezing your cigars is an extreme measure to be used only in case of bug infestation at the risk of damaging the cigars (but getting rid of the bugs is a victory of its own!)
Cigar etiquette is polite behaviour when smoking a cigar. For example, in 19th century Havana, it was considered an insult to give another smoker a light from your cigar without first knocking off the ash from the cigar. Another breach of etiquette was to pass on a cigar to a third-party for them to light up too - loaned cigars should instead be returned with a polite flourish.
Rules of cigar etiquette were published in 1967 by Swiss tobacconist Zino Davidoff in his essay entitled "Zino Davidoff's Guide to Cigar Etiquette." The essay calls for cigar aficionados to do such things as smoke the cigar only halfway, let it burn out on its own, never ask another smoker for a light, refrain from smoking while walking, etc. Davidoff dismisses the elaborate rituals of lighting, says that removing or leaving the band are equally correct, and insists that a gentleman never relights a cigar that is more than two-thirds smoked.
Cigar Aficionado's book Cigar Companion suggests two sets of rules: one when among non-smokers, and another when among cigar smokers. One should never smoke except where smoking is appreciated, and care should be taken to minimize criticism from non-smokers from the smell of smoke in one's home or on one's clothes. Among other cigar smokers, it suggests rules governing sharing, cutting, lighting, humidors, women cigar smokers, and gifts. It concludes with one ironclad rule: never give a prank exploding cigar, and do not associate with anyone who does.