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Time

You should pick a cigar for the amount of time you have available to smoke. If you are at a sporting event or on a golf course, choose a longer cigar that will last for a long time. If you are in a cigar friendly restaurant and you want to have a nice after dinner smoke, choose one that will last about 30-40 minutes. As you experiment with different sizes you will find one that you are most comfortable with.

Construction

A cigar is made up of filler, binder and wrapper leaves of tobacco. The outermost layer, the wrapper leaf, is the most flavourful part of the cigar, contributing to around 80% of the flavour of the whole cigar! When a cigar is thicker, there is proportionally more filler and binder tobacco than in a thinner cigar. When you smoke a thicker cigar, the flavourful wrapper leaf may get a little diluted by the filler and binder tobacco. If you are after a punch of flavour, then sometimes, smaller ring gauges, which are made up of more wrapper leaf, can offer a more concentrated flavour.

Thickness

The thickness of a cigar often has an impact on how hot it burns. A thick cigar will burn slow and cool, while a thin cigar will burn faster and hotter. This is one of the reasons why a bigger cigar takes longer to smoke than a thinner cigar. Be careful when smoking a thinner cigar, if you've picked a smaller smoke, you might be in a rush, but this shouldn't mean you should puff faster. By smoking faster, you are likely to raise the temperature of the cigar, which can contribute to burn issues and bitter tastes.

Length

The length of a cigar determines how quickly the heat reaches your palate. The shorter a cigar, the closer the lit end is to your palate, so you'll experience the flavours of the smoke faster, and more intensely.
As such, a longer cigar may allow you to enjoy subtler tasting notes as they emerge throughout the smoke, whereas a shorter cigar may give you an immediate, bold smoking experience.