While smoking is generally considered an undesirable practice, there are times when the occasional cigar is a merited reward or novelty exclusive to no man: provided he knows how to smoke it.
Any quality cigar lounge will have cases upon cases of cigars of every size and color displayed prominently from within their humidors. Each box will have two numbers on it. The first is the diameter of the cigar in 64ths of an inch. The second number, which indicates the length of the cigar, ranges from 1 to (usually) 9 inches, but as with all things there are exceptions.
Cigars range from a light, almost greenish-brown color to a black. The outer wrapping leaves determine the overall color and shape, while the interior filler leaves determine the flavor. A good rule of thumb is that the darker the cigar, the stronger the flavor, and the more blue the smoke. Likewise, lighter cigars may have a gentler taste and a more white, billowing smoke.
Typically, the smell of the wrapping on a cigar is roughly the flavor one can expect to have on their lips as they smoke it.
Once a selection has been made, there are two options: use a cigar punch and drive a hole in the bottom of the cigar, or invest in a quality guillotine cutter, and remove the cap. To cut a cigar, look to the cap for where the binding leaves connect with the outer wrapping: there should be a narrow ring of leaf where the wrappings change direction. Slide your cutter to the point that the blades are resting lightly on the ring, then firmly and smoothly, close the cutter and remove the cap.
From there, the rest is rather simple: inhalation is optional. Use wooden matches to preserve flavor, and turn the cigar when you light it to ensure an even burn. Leave about 3/4 of an inch of ash on the ember to act as insulation, when the glue on the label starts to melt, remove the label and discard it appropriately.
There is, however, a certain measure of etiquette that goes into cigar smoking. If at a party or restaurant, check with the host or hostess that smoking a cigar is permissible, after all the goal is to enjoy yourself and not disrupt someone else. Do not ash more than is necessary, and try dispose of your butt properly: nobody has any desire to see you walking around with a sodden stump of stogie hanging in your mouth.