There are a few things you can do to enjoy a cigar a little more than if you had not known how to at all. It can be frustrating to pay $8 for a premium cigar and not enjoy it.  Sometimes people don't even realize that if they had stored it right, cut it right, and then smoked it right, they could have really enjoyed that $8 smoke. Just like the other finer things in life, they were meant to be handled in a certain way.  Premium hand rolled cigars aren't anything like the machine made cigars you find in the grocery store.

Selecting

Some folks suggest a mild cigar for someone that's new to cigar smoking. Reason being that a full strength cigar can be too full, or too spicy. Your pallet changes and just like beer and wine, cigars are an acquired taste. Don't buy cracked or discolored cigars. And for god's sake, don't stand around in a tobacco shop sniffing cigars. No one wants to buy a cigar that's touched your nose. It is okay to gently squeeze a cigar to see if it's been stored properly. A good cigar should feel some what supple.

Cutting

I’m a fan of punches. They’re cheap and they work great. A sharp double blade guillotine cutter is convenient too. It does the job and fits in your pocket. You don't want to ruin a five-dollar smoke by biting the cap off though. Gently close the blade 1/16" from the tip of the head then give it a quick, controlled slice. Don't cut more of the head off than you need too. The head holds the wrapper in place and with out it, it’ll will unravel. The binder really doesn't taste good and will suck the moisture out of your lips, making for a disappointing and upsetting experience.

Lighting

A butane torch or wooden matches will give you a more pure taste by not introducing chemicals and fumes. Allow the sulfur to burn off the matches first. Bunching two or three matches together will obviously give you a bigger flame. Toast the foot of the cigar by holding it at a 45 degree angle and rotating it above the flame, but don't let the cigar touch the flame. Most of a cigar's flavor comes from the wrapper, you don't want to scorch the wrapper and burn the flavor before you ever get to the first draw. So never let the flame touch it. After you've toasted the foot, hold the cigar in your mouth with one hand and place the flame ~3/4" under the foot and rotate the cigar while puffing. When you see a big flame, (you'll see what I mean if you did it right) it's lit. Don't let that flame burn too long. Take a few more puffs and let it burn on it's own for a minute or two to stabilize. You should now have a perfectly lit cigar with an even burn.

Smoking

DON'T INHALE - it's a good way to make yourself sick. Just draw the smoke into your mouth and savor it, without holding it in long enough to burn your taste buds; And of course a good strong drink like scotch or a full bodied red wine can turn a good smoke into a great smoke! How much of that cigar you get to enjoy is up to you and the brand. Not all cigars are worth smoking all the way to the head. Cheap cigars will develop an after-taste and even premium cigars that haven't aged enough will too. Relighting When your caught up in a conversation and your smoke stops smoking, blow once through the head to push out the foul gases left inside then relight it. It's not worth relighting a cigar that went out a few hours ago though. And you'll really regret lighting a cigar that went out yesterday; Don't believe me? Try it sometime.

Extinguishing

Don't snub it out. That just makes an awful smell which is poor etiquette. When you're done with your cigar, just set it in an ash try and let it go out on it's own.