From what I've seen of "Proper" cigar smokers. You trim the end, light it with a wooden match, put on an expression that gives the appearance of being severely constipated, chomp down and clamp it firmly between your incisors, and take slow, long draws, making sure not to hotbox it. Pretty good for a non-smoker, eh?

I puff a couple of times then inhale. I like mine with tips.

like this:

Yes, there is a lot of etiquette that is just silly. BUT don't use a match to light it, use a butane lighter because it's gas is tasteless and won't contaminate the cigar. Try and get it to burn evenly by rotating and puffing 3 or so times but don't get it too hot or it will not taste good ("burned" smoke). Honestly, it's more difficult to cut off the end properly than light and smoke it. My personal preference for 42 ring guage (an average size cigar) or less is a cigar punch, and a double bladed cutter for larger.

There is no real "proper" way to do it, but it helps if you do use butane lighters. I find that a punch helps keep the cigar from falling apart on you too. It also helps if you have a profound, contemplative look on, just adds drama.

If you decided to try cigar smoking for the first time, put off this occasion for the weekend or evening after snacks or the main dish; alone or with your friends. Good cognac or whisky should be by your side. Sit down comfortably in the armchair and ask your relatives not to disturb you for some time. Try not to touch cigar ribbon because cigar outer envelope may be spoiled. You can remove it at the end of smoking if it disturbs you, it will become more pliable by this moment. If cigar tip is closed, cut it off carefully almost up to the whole thickness, using special cigar guillotine cutters (or sharp knife). With this the part of the top should remain on cigar in order outer envelope does not come unrolled. Use cigar matches or butan lighter for lighting. Heat up your cigar during several seconds, holding it at the distance of 2,5 cm from the short flame. Puff at cigar, rotating and making small inhalations, such techniques provides straight burning. The process of lighting up may take about 3 seconds. You should smoke easy, intensive smoking does not give you true pleasure, as cigar becomes hot, and the flavor is too strong. The chosen temp of smoking is a compromise of cigar morphology, its strength and inhalation, you temperament and receptivity to flavor and strength. If cigar is off, shake off ashes carefully, warm up the tip and light it again. Taken from http://www.saveonsmoke.com/news/view/2009/07/22/instruction-to-smoking-a-cigar.html