Baffo's guide for the beginner cigar smoker

OK, so you want to try smoking a cigar. Maybe because you wonder what the hype is all about, maybe because all that Clinton business turns you on, maybe because you saw people smoking cigars with great enjoyment, and you think that you will like it.
Just as long as you don't do it because you think it makes you look cool - that would be the silliest reason.
But you never smoked a cigar before ! How do you go about it ? Easy.

Choose a cigar

Choose a good cigar. What is a good beginner cigar ? It is one that is not flavored with cognac, maple, gerbil hair or anything. It is one that does not came with a "It's a boy !" wrapper.
It does not have to be expensive, either. Cuban is great, unless you are being embargoed, in which case you can get great cigars from Honduras, Mexico (Te Amo is OK, Cruz Real is too), Nicaragua, even from Italy (a nice toscano)!
What is most important, is that it has to be fresh. Cigars have to be moist (70% relative humidity), and they do not really keep well unless stored with extreme care. So get it from a shop that has a lot of trade. The cigar you found in a box in the attic probably will not be a good one. A cigar that has been kept in a humidor, on the other hand, can be good even after years.
A dry cigar can be told by gently rolling it between the fingers: if it makes crunchy noises and sheds bits of tobacco, or if it feels very light, it is probably dry and will not be good.

Cutting the cigar

Get a very sharp blade, like a razor blade or a really sharp penknife. Carefully cut a little round piece of the external tobacco wrapper from the closed rounded end of the cigar. This will expose the filler. A very shallow cut is usually enough. I have found Cuban Cohiba cigars that had a somewhat thicker hide, and that required a deeper cut.
Why do you cut the cigar ? The rolling process leaves the cigar open at one end (where you will apply the fire), and close at the other end (where you will apply the mouth).
But to be able to suck air through the cigar (a complex definition for the simple act of smoking it) you need to open the closed end.
If you decide that you like cigars, later on you may want to get a specialized cigar-opening device. Some of them look like little guillotines. I like a penknife. Give the cigar a little experimental suck: you should feel resistence, like sucking on a drinking straw, but air must come through.

Notice that some cigars, like the toscano, are meant to be cut in half. Since the cigar is a bit pointy at both ends, you get two half-cigars with a wider end, which is the one you light.

Lighting the cigar

Cigar purists claim that they light cigars only with cedar splints, not with matches. Whatever. As a beginner, you will not be able to tell the differece. I would use a butane lighter.
The idea is to light evenly the whole end of the cigar, which can be a bit difficult with a big cigar. Anyway, my method is to char the end of the cigar while rotating it before I start puffing. Then, I put the cigar in my mouth, apply the flame and suck (CAREFULLY !), rotating the cigar slowly - this is the trick.
Then take the now-smoking stogie out of your mouth and inspect the embers. If you see a nice uniform cherry, all is well. Some cigars will require a second round of lighting. Don't worry, it is OK. I confirm what Rollo said above: if the cigar does not go cold, you can relight it.

Smoking the cigar

(or, how not to cough up your lungs)

Cigar (and pipe) smoke is NOT like cigarette smoke. It is much more potent. It is meant to stay in your mouth, and it does not go in your lungs. If it goes there, you will feel as if you had swallowed a file, a rasp and a bag of nails.
So, at the beginning, puff carefully. And taste the smoke with your tongue. Take it easy. Smoking a cigar is a somewhat slow experience, best done when you have a bit of time and quiet.
Notice that an unattended cigar will go out in a minute or two - but it can be relit without difficulty.

Cigar ash is much harder than cigarette ash: this means that you can easily accumulate a good inch and a half of ash, without risk of it falling off. Don't keep tapping your cigar obsessively.

In good company

I don't know if it is just a preconceived idea, but I noticed that cigars go well with some really powerful alcoholic drinks: straight rum, tequila, grappa. All of them at room temperature, at least that's the way I like it.

Social acceptability

Did I mention that a cigar produces a lot of very powerful smoke ? This means that you should try it somewhere that you do not mind smoking up.
Your parents' living room probably is not OK.
Cigar smoke also flavors things, like your hair, your clothes, curtains and if you have an open closet ... you get the picture.
Porches are great. Cigars make you understand the Victorian fuss about the gentlemen retiring to the parlor to smoke.

Disposing of the dead

When the cigar gets too hot for your lips, it is time to stop smoking it and put it in an ashtray. Do not crush it, for it will stink. Just leave it there, it will stop burning by itself.
Notice that a dead cigar butt after a while stinks terribly, so after an interval you would do well to empty that ashtray.
Endly, remember that a cigar is a much bigger fire hazard than a cigarette.

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This guide comes from personal experimentation