Cigars 101 - How to Select, Smoke and Enjoy Hand Rolled Cigars

If you're ready to join the ranks of cigar smokers, here is how to get started. The first step is selecting the right cigars to "practice" with. You should start by choosing several different single cigars at your local tobacconist. Do not buy a box of cigars until you have sampled a few singles, first. Don't be afraid to ask the owner or manager for advice.
Choose Mild Cigars
Mild cigars are recommended for beginners, since the more full-flavored cigars would most likely taste too strong (or just plain bad) to a new smoker. Mild cigars are also the least expensive, so you won't have to worry about ruining an expensive cigar by lighting it incorrectly, or by cutting too much off the closed end.
Inspect the Cigar
Once you have determined which type of cigar(s) to purchase, then gently squeeze the cigar to determine if there are any hard or soft spots. You don't want to take a chance on buying a cigar with a bad draw, or worse yet, one that is plugged and not smokeable. Tip: Reputable tobacconists will usually replace a plugged cigar. Also, inspect the wrapper for cracks or discolorations.

If you do not yet own a humidor, do not buy more cigars than you can smoke within a couple of days, and make sure to leave them in their cellophane packaging (if applicable) until you're ready to smoke. Never leave an unprotected cigar exposed to the elements, as it will quickly dry out. You can temporarily store cigars in a Tupperware or similar container.

Now that your cigar is all fired up, it’s time to smoke and enjoy it. Continue to puff and rotate about every 30 to 60 seconds. Do NOT inhale the smoke, just taste it in your mouth and blow it out. If you smoke a cigar too fast, it will burn hot and ruin the flavor. If you smoke too slow, it will go out and you will have to keep relighting. Since most hand rolled cigars are made with long filler, you will not have to flick the ashes until they are at least ½ to one inch long, depending on the cigar (and any wind conditions, if you are outdoors). You can smoke a cigar as far down as you wish, depending on the taste.
Drinks to Accompany a Cigar Are Important
Other than the taste and draw of the cigar itself, the drink chosen to accompany a cigar is the second most important factor that will affect your enjoyment of the smoking experience. If comparing different cigars, always make sure to have the same drink. Many drinks are compatible with mild cigars, but as you move up to medium and full flavored cigars, it is important to choose a drink that will not be overpowered by the flavor of the cigar. Coffee drinks, port, scotch, brandy, and most drinks made with Kahlua can accompany any cigar.