
Quickly and decisively, but before we get into that lets talk about "where" to cut.
The proper place to cut depends on the cuban cigar. First you need to closely examine the head of the cuban cigar. You are looking to see just how far the cap (this is the round of tobacco used to seal the head) extends down the barrel. On a parejo (a parallel-sided cuban cigar) this is typically 1/4" - 3/8"; wherever the caps stops you should regard as your limit as to how far down you should cut.
The best cut is one above this "cap line" that will open up 75%-85% of the cigar's surface. You want as large an open cut as possible so as to allow for an easy draw, but you do not want to cut beneath the cap line as the cuban cigar may start to unravel on you. Sometimes this means a thin cut of 1/32" is perfect, while other times you may need to cut 3/8" - it depends entirely on each cigar's construction.
For figurados such as torpedos, perfectos, etc. you may have to cut significantly more in order to open the head enough for a sufficient draw. How far is a personal question. Typically people smoke cigars with tapered heads because they like how the narrowing ring concentrates the smoke against the palate, so unlike with a parejo, most figurado smokers want less of the cigar's surface opened by the cut. And because of their shape, figurados seldom unravel even when cut beneath the cap line, so it really is a judgement call. Personally, I suggest you cut less to begin, smoke the cigar for awhile, and if you decide you wish for a more open draw just recut.
As I said before the key to a good cut is to be quick and decisive. Once you find your spot, you should not hesitate - just clip it. Quick cuts tend to be cleaner cuts, however you must have the right tool to do this well. The prime criteria of any cutter is that it be very sharp, the sharper the better.
Most single bladed guillotine cutters are inadequate, so I suggest you opt for a double bladed guillotine if possible. Typically double bladed cutters work better as the two opposing blades work together, however there are exceptions to this. There are some single bladed cutters that work great and some double bladed ones that are just plain junk. Single or double what is important is that the cutter be sharp because if it isn't you will just end up crushing the head of your cigar.
There are a quite a few other tools you can use to cut a cigar.
One that is frequently seen in cigar store counters an in the movies is a pair of cigar scissors. Personally, I would steer clear of these, they look cool, but most of them just plain stink. They are seldom sharp enough and it is very common for the smoker to torque the scissors blades while trying to cut a cigar resulting in ruined smoke. If you do decide to buy a pair of scissors, buy the best you can afford. And practice a bit on some very cheap cigars before attempting to use them on a premium cigar.
Another option is to use a punch cutter. These are very easy to use as they simply punch a hole in the head of the cigar of a fixed diameter. All you need to do is line the cutter dead center and twist. These can provide a very clean cut and their only real drawback is that most do not cut a large enough hole for 50+ ring cigars and this may not be an issue for you.
A unique cut is a "v-cut". This a cutter that cuts a v-shaped notch from the head of your cigar. Another unique cut is the "cat's eye" which is very similiar to a v-cut however the edge of the cut is curved rather than straight. Both of these cuts tend to concentrate the smoke on the center of the palate, some folks swear by these cuts while others hate them. Both of these styles of cutters need to be super sharp to work well.
A sharp pen knife works well also and with some practice you can become pretty adept at cutting a cigar's cap with your teeth. I know people who use their fingernail and a couple of others who actually jab a pencil into the head of their cigar to prep it for smoking. So in the end it really is a matter of personal choice and with a little practice you will find the technique that works best for you.
And if you managed to read all of this, here are a couple of quick, neat cutting tricks:
If you lay a guillotine cutter down flat on a table then insert the head of your cigar so that it rests against the table's surface then clip, you will almost always take off the right amount on most cigars. Try it...
If all you have is one of those cheap giveaway cutters, try cutting your cigar with it still in the cellophane sleeve. This technique will produce a much cleaner cut with a duller cutter.
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