Smoking a cigar is very unlike smoking a cigarette. The right time to ash a cigarette is when the ash becomes inconveniently long. The tobacco in cigarettes is cheap and hot-burning. Conversely, the tobacco in a cigar is expensive and burns best when it's kept at a lower temperature. This ensures the very best flavor.
The first few puffs of a cigar always entail the hottest ember. The flame generated by high-end cigar lighters, such as a Colibri lighter, is very hot and, thus, is held a bit back from the stogie. However, the ember still needs to cool a bit before the taste is at its best.
The more ash, the cooler the ember. Too much ash will actually extinguish the ember altogether so one must endeavor to keep the ash to a reasonable level. Too much of an ash will also mean a hard draw. Depending on the tobacco being smoked, one may be able to smoke with a longer ash or the density of the tobacco may mean that the cigar needs to be ashed quite frequently. Keep experimenting to see what works for any given brand of cigar.
The ash also affects how easily one can draw off of the cigar. Of course, a thicker, heavier ash means that it will be a harder draw for the smoker. No ash means that the draw will be very easy but also may mean that the ember will be burning too hot to ensure quality flavor. The art of cigar smoking involves finding a happy medium between the two. It may take some time but, then again, all worthwhile things have that quality to them.
The only other concern of which one should be aware has to do with being outdoors. If one flicks their ash too early, it may pull the cherry, or part of it, off of the cigar along with it. This can result in a fire hazard and should be something toward which one should give proper attention. A longer ash will tend to drop off under its own weight. Let it detach a bit on its own before ashing to make sure none of the burning tobacco is pulled away with it when one is in a dry area.
Dave Sabot is the owner of an online specialty lighters store featuring windproof lighters and cigar reviews.