Choose Mild Cigars
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.
Inspect the Cigar
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.
Protect & Smoke
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.
How to cut a cigar
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.
How to light a cigar
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 smoke and enjoy your cigar
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.