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An excellent cigar is bliss. It is reward for a job well done, solace for a day gone wrong, companionable treat for a long night of work, or stimulating wake-up to go with morning coffee. A fine cigar, if it’s the right cigar, makes the best of times perfect and the worst of times immeasurably better.

It follows that your discernment in choosing cigars—in being able to separate the sheep from the goats—can materially boost your well-being, repeatedly, for the rest of your life. A bad cigar, or even just the wrong cigar for a given occasion, is a waste. This means knowing excellent cigars on sight is no frivolity; it is a practical, useful life skill.

Remember first: Cigar enjoyment is particular to each individual because every person’s body chemistry is unique. A cigar that another person finds heavenly might make you gag, and vice versa. There aren’t a lot of shortcuts to your own best cigar knowledge: Experience is indispensable. (But that kind of journey is its own reward.)

Remember, too, that price is not a perfectly reliable gauge. You can splurge on a $23 beauty, but if its flavor profile does not mesh with the predilections of your own taste buds, then you’re splurging on a dead loss. Some smokes that run no more than a buck and a half are far superior to ill-conceived blends costing 10 times as much.

You have to find what appeals to you. And the real trick (for most of us) is finding cigars you love that are also affordable. It’s no different with wine lovers. They surely have some very nice, expensive bottles tucked away in their collection to show off when they want to impress friends. But chances are their “go-to” dinner selections come from the bargain shelf, because they have learned that certain inexpensive wines taste very good to them.

A few obvious cigar characteristics to look for:

Cap – Single, double, triple? The cap covers the head of the cigar, the end you put in your mouth. It keeps the cigar from unraveling. A single-capped cigar can be very good, and a triple-capped specimen might sometimes disappoint. Still, the presence of multiple caps shows at least that the manufacturer is making a gesture toward quality. A triple cap is an extra expense not likely to be blown on an inferior smoke. A multi-capped cigar shows the maker is probably trying to offer a premium, good-tasting product.

Color of wrapper leaf – This often indicates how light, or heavy, the cigar will taste. Many people incline toward a small, blond cigar early in the day and a larger, darker cigar after supper. Also, darker often means sweeter (sometimes bringing a sort of molasses tone), but darker can also indicate a smoke that is heavier in both flavor and nicotine, even if it is sweeter.


Nice ash? – Does the ash hold on, intact, without flaking, for more than an inch? High-quality, long-filler cigars will generally hold an ash very well, whereas low-quality, short-filler cigars … not so much. Allow your attention to wander and a cheap, flaky ash will land in your lap. Long-filler cigars taste better (generally) because thought and care goes into their construction. Short-filler cigars are usually machine-made—casual, quick smokes, not meant to be taken too seriously.

About “shaped” cigars – Perfectos, Torpedos, Salamones (search for these terms in Google Images)—these require greater skill by the roller, and creating them usually goes to the most experienced rollers on a factory floor. For these reasons, shaped cigars often contain some of the better leaf in a cigar maker’s warehouse. They can cost a bit more, but chances are you will notice a satisfying difference in flavor.

None of these indicators is infallible. One of the perverse joys of true cigar mastery is finding the ugly ducklings that taste (to you) like ambrosia. But armed with just a few tips, you can minimize the boondoggles as you home in on the perfect stash for your personal humidor. Happy hunting!

For more, check out how to cut and light a cigar properly, how to review a cigar, and our guide to candela cigars

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