As a general rule, cigars with larger ring gauges tend to be fuller flavored (there is normally more ligero and less volado in the blend), smoke more smoothly and slowly, and heat up slower than those with small ring gauges. They also tend to be better made than the smaller ones (which are the sizes recently qualified apprentices start on).
Cigars with small ring gauges often have little or no ligero tobacco in the filler blend. If there is no hurry, large ring gauge cigars are almost always the preferred choice of connoisseurs or experienced cigar smokers.
The beginner, however, is advised to choose a relatively small cigar, say a minuto or carolina, and then move up to the bigger sizes of a mild brand (see The Cigar Directory). Jamaican cigars, such as Macanudo (also made in the Dominican Republic), tend to be mild, or try H. Upmann among Havanas. A cervante is probably the best cigar above the corona size to move up to when you feel you have gone beyond the beginner stage.
A number of cigar experts, including the legendary Zino Davidoff, have pontificated about a person's physical appearance related to cigar size. The Cubans have a saying: As you approach 30, you have a 30 ring gauge; as you approach 50, you have a 50 ring gauge. It is true smoking a fat cigar can sometimes look rather comical or pretentious if you are very small or thin. However, on the whole, this is basically hogwash. What size of cigar you smoke is entirely up to you and your wallet. But there is a case to be made about what sort of cigar to smoke at what time of day. Most smokers prefer milder, smaller cigars in the morning, or after a light lunch. The seasoned smoker, however, might go for something like a robusto after a heavy lunch; a lot of flavor packed into a reasonably short smoke. Certainly, most experienced smokers prefer a big, full-bodied cigar after a heavy meal or late at night, partly because a thin cigar will not last very long, but also because a mild one isn't so satisfying on a full stomach. So they will select a belicoso, Churchill, or double corona. By the same token, smoking a heavy cigar before dinner is likely to spoil your appetite and play havoc with your taste buds. Much the same consideration applies when people have strong drinks like port or brandy after dinner, rather than something lighter, which they will take before or during dinner. If you want to compare cigars, it is best to smoke them at similar times of day, taking meals and location into account, too.
When you choose a cigar, you should first make sure that the wrapper is intact (if not, reject it) and has a healthy sheen. You should also make sure that it isn't too dry or brittle (otherwise it will taste harsh) and that there is a noticeable bouquet (if not, the cigar has probably been badly stored). A good cigar should be neither too firm nor too soft. If the wrapper is heavily veined, the cigar should be rejected: quality control let that one slip by accident.
The color of a cigar's wrapper (and that part of the filler that you can see) will give you some clues as to its quality, though it is a fallible test since the filler blend is the key to its flavor. As a rule of thumb, the darker a cigar, the more full-bodied and sweeter (since darker wrappers contain more sugar) it is likely to be. Cigars, if properly stored, continue to mature and ferment in their cedar boxes. This aging process during which a cigar loses acidity is not unlike the maturing of good wine. Fuller-bodied cigars, particularly those with big ring gauges, tend to age better than milder ones. But, it should be noted that some full-bodied brands such as Cohiba and Montecristo (apart, perhaps from the very largest sizes) don't age particularly well because the tobacco is fermented for longer period than normal cigars (a complete extra fermentation in the case of Cohiba), thus leaving little room for further maturation. There are even those who argue that if tobacco has been properly fermented, it is very unlikely to mature further (and if it has been fermented too little, it cannot mature at all).
Milder cigars, particularly those with pale wrappers, will merely lose their bouquet if kept too long. In general, you should smoke lighter cigars before darker ones. Wrappers that are destined to age well start off oily, and get slightly darker and oilier as they mature.
Most importers of fine handmade cigars take care to age them a little before releasing them to the public (about two years for Havana cigars taken into Britain). There are no hard and fast rules about how long cigars should be left to mature (it can often be a matter of luck), but some experts state that cigars aged for six to ten years will be in the peak of condition. Others warn, quite rightly, that even if they are stored under ideal conditions, most cigars will slowly lose their bouquet. If storage conditions are less than ideal, they will also become dry. Even if properly stored, it's probably sensible not to keep cigars for more than 10 years. By that time, they're unlikely to get any better, and almost certainly will have lost some of their bouquet.
Cigars should be smoked either within three months of manufacture or, failing that, not for at least a year after they are made. The intervening "period of sickness" as it is known, when the maturing process starts, is the worst time to smoke a cigar.