Cigar 101 - 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.
No Cigar Cutter?
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 a hole 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!
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*Article from cigar.about.com