You just graduated summa cum laude from college. You're walking off the stage after giving your valedictory speech (which was great, by the way - we loved the joke about the nun, the eskimo, and the feral midget!), when your uncle Stan walks up and places something in your hand. It's long, brown, and smells kinda funky. It's a cigar.

For all you know, cigars are just fat, smelly cigarettes. Like many young people, you know that cigars exist, you know that they can be expensive, you know that they're becoming trendy, and you may even have tried one before. But you still need to be reminded which end goes in your mouth, you're not sure about the part when you "clip off the end," and you still haven't gotten the hang of that whole "don't inhale" thing.

Fortunately, we're here to help. With this SYW, you'll learn your wrappers from your binders and your Upmanns from your Ashtons. We will teach you how to squeeze the most enjoyment out of your puffs or, at the very least, make it seem like you do. And you'll finally understand why it's less appropriate to compare cigars to cigarettes (highly inappropriate) than to compare them to fine wines (slightly more appropriate).

1. KNOW THE DANGERS

OK, we're not gonna get all preachy or anything. You already know that cigars are bad for you, but since you're reading this SYW, you probably don't care. Just note that we love you so much, that we thought this note deserved its own step.

Remember all the stuff you hear every day about cigar and cigarette use: nicotine is addictive, the smoke can harm unborn fetuses, and your chances of getting cancer increase dramatically. Also be sure that whenever you smoke a cigar, that you check with everyone in the vicinity to make sure they approve -- cigar smoke can smell quite strong. But you're an adult. You'll do whatever you want anyway, so we might as well help you make sure that you do it right.

And on that note, on to learning about stogies!

2. LEARN WHAT A CIGAR ACTUALLY IS

Cigars are made of three kinds of tobacco leaf from many different strains of tobacco plant. The three leaves are wrappers, fillers, and binders:

  • Wrappers are the part of the cigar that you see-the long, supple leaves that come from the widest portion of the tobacco plant.

  • Fillers are the meat of the cigar-the rolled-up bunches of leaves in the middle.

  • Binders are elastic leaves which hold the filler bunches together.

The strains of tobacco plant yield vast ranges in flavor and quality of tobacco, the best of which is grown in the Vuelta Abajo region of Cuba. Thanks to Uncle Sam, however, no Cuban cigars can be sold in the USA (didn't you see that episode of Seinfeld?), so only quick excursion to Canada will allow you to enjoy what are widely considered to be the best cigars. Fortunately, though, fine tobacco from places like the Dominican Republic, Honduras, and even Connecticut can still be sold and purchased in the USA.

The most visible characteristic of tobacco is its color, and fortunately, this will tell you a lot about the cigar you are about to purchase. The colors range from claro (light brown) to oscuro (almost black). If this is all French to you, you are a horrible linguist, because these are Spanish terms. If the words still mean nothing to you, don't worry. All you need to know is this: tobacco is either grown in the sun or in the shade. Sun-grown tobacco leaves are more robust, heavily-veined, and darker. This makes for a more powerful, robust flavor generally best suited for true aficionados or your grizzly grandfather with one remaining taste bud. Shade-grown tobacco is more delicate and much lighter in both color and flavor. If you're smoking your first cigar, opt for the lighter-colored claro.

3. CHOOSE A CIGAR

So now that you know what it is that you'll be smoking, it's time to choose from the hundreds of varieties that are available to the cigar buyer. Granted, most people won't know that the cigar you choose is any better than a drugstore brand, but there really is a distinct range in quality. Like wine, cigars can be enjoyed by many but truly appreciated by few. Unlike wine, cigars are solids.

Size
Man-made vs. machine-made
Brand
Cigar shopping

Size

Size is measured in two dimensions: length and ring gauge.

  • Length refers to a cigar's length. (You can read, right?) Length can range from the baby-sized 4-inch Petit Corona to the monstrous 8-inch Double Corona (it's like smoking a ruler!). The most common cigar sizes are 5 - 6 inches. The Davidoff store in London boasts a cigar a yard long. (They are afraid to light it up, as scientists have predicted that the ashes will crush and kill any passersby.) Generally, we suggest that you choose a 5 - 6 inch cigar, avoiding larger sizes like Churchill or Double Corona.

  • Ring gauge refers to the diameter of the cigar in the center (how fat it is). Ring gauge, the cigar's diameter, is measured in 64ths of an inch. Therefore, a ring gauge of 40 indicates a cigar that is 40/64 inches wide. A ring gauge of 55 indicates 55/64 inches. Ring gauge also affects how much smoke you suck of the end; a larger ring gauge (And thus, wider surface area) means that you're gonna get a deep sense of the flavor with every puff. We suggest that you start of with a smaller ring gauge (ask the salesperson for some recommendations), and work your way up.

Man-made vs. machine-made

Microchips are best made by machines; cigars are not. As you probably guessed, the highest quality cigars are painstakingly rolled by hand, and it shows. Machine-made cigars, which can be mass-produced quickly and cheaply, are usually made of broken scraps of tobacco leaves that are unsuitable for hand-rolling. Therefore, they smoke less evenly and burn more quickly. It's pretty easy to tell if a cigar is machine made by looking at the wrapper -- if you see lots of seams suggesting that it's more of a patchwork of tobacco than continuous leaves, you're looking at a machine-made cigar. So opt for a man-made. Higher-end machine-made cigars look (and even smoke) like man-mades, but the highest quality cigars are still carefully made by bona fide human beings.

Brand

The brand of cigar is its most important quality, at least in a superficial sense. This is not to say that different cigar brands necessarily differ in flavor or quality, but everybody knows that a nice Cohiba is "nice" merely because it's a Cohiba.

Because different brands feature different varieties and sizes, no one brand can be pigeon-holed by any factor other than the general quality that goes into each of its cigars. The most legendary brands, like Cohiba and Monte Cristo, are Cubans and thus hard to find. Instead, we recommend that you start throwing brand names around like Arturo Fuente, Macanudo, Dunhill, Davidoff, and Ashton, which are all legal here in the US.

Note: many Cuban brands such as Cohiba and H. Upmann are also manufactured in other countries, but they're not gonna be anything like their Cuban brethren. It just happens to be that the cigar-making factory also gets tobacco from other countries. So if you find a nice, high-priced Cohiba in your local tobacco store, don't wink knowingly at the manager - he's not selling Cubans.

Cigar shopping

Cigars are a luxury item, and the service at cigar stores should treat it as such. So here's our advice for how to handle yourself in a cigar store:

  • Expect the employees to be very helpful in helping you choose a cigar. They're trying to get you hooked on a delicious brand so that you become a repeat customer.

  • Do not hesitate to ask to see a cigar up close. Handle it lightly to check that the cigar is kept at a proper moisture level-it should feel supple and not brittle, but it shouldn't drip water all over your sleeve.

  • Do not roll the cigar near your ear or smell it up close. These supposedly sophisticated means of inspecting cigars are not only unsanitary, they are also pretentious and will tell you nothing.

  • Feel free, however, to take a light sniff of the cigar's bouquet to see if it is agreeable.

  • The cigars in the box should be neatly arranged, with the color running from darkest to lightest and the spiral of the wrapper leaves running in the same direction. These measures are checked in quality control at the factories; if things are out of order, the cigars either slipped past quality control or have been messed around with.

4. SMOKE THE CIGAR

Many people think that the proper way to smoke a cigar is to set one end on fire and just suck like crazy on the other end. It's a tad bit more complicated than that.

Before we teach you how to actually smoke the cigar, consider that many people like a nice drink to accompany the cigar's taste. In fact, you might want to consult some of our other SYWs about exactly what drink might be right for you. The most traditional drinks when smoking are port, cognac, bourbon or scotch, and complementary wines such as Cabernet Sauvignon. The key here is that the drink will stand up to the powerful flavor of the cigar without diminishing it.

Cutting

Cigars are made with a cap over the head. Most good cigars, therefore, have only one open end. This is NOT the end that you put in your mouth - that open end is where the smoke comes out. So you need to cut the cigar at the head.

Cutters come in different styles, but the most common is the guillotine. The double-bladed guillotine has a hole in the middle, two blades, and two notches where your fingers can grip it. You should absolutely buy a guillotine as your cutter - they're easy, small, and they make a clean cut with less of a tendency to tear the tobacco than other styles. You can also use a knife or your teeth, but cutters are really cheap, and a knife may ruin the cigar.

Here's how to actually make the cut (it's really simple):

  1. Cut the cigar on the tapered part (the cap).

  2. Try to leave about 1/8th of an inch of the cap.

  3. Never cut on or past the cap line - you'll be cutting the wrapper leaf. All hell will ensue.

Lighting

This can be tricky for a newbie, but our tips will get you through it:

  1. It's best to light a cigar yourself - lighting a cigar takes longer than lighting a cigarette, and it's best not to feel rushed by having a friend reach over with a lit match.

  2. Matches or butane lighters are fine, but if you use a match, make sure the sulfur is burned out first so it doesn't impair the taste of the cigar.

  3. Never use a candle - the wax particles will enter the cigar and taint its flavor.

  4. Hold the cigar in your hand, not your mouth, and rotate it near the flame.

  5. Do not actually touch the flame with your cigar.

  6. When the entire surface is charred and embers appear, place the cigar between your lips.

  7. Gently puff to blow out any foreign particles or odors that may have come from the lighter or match. Check to see that the cigar is lit evenly.

  8. This probably goes without saying, but just in case you happen to have a pompadour with a lot of hairspray: remember to not set your hair on fire.

Smoking

Now that the cigar is lit, you should be able to draw smoke gently through it.

  1. Draw slowly by pulling in your cheeks. Do not suck or inhale.

  2. Do not smoke the cigar too forcefully or quickly - it will make it taste harsh and burnt. Just puff occasionally, making sure the cigar stays lit.

  3. After a few minutes, you may want to remove the cigar band (label). Some people think it is obnoxious to keep the band on while you smoke, and it's not really necessary to keep your fingers from getting stained. Make sure that you've smoked the cigar for a bit, though. If you remove the band too early, the glue will not have softened and you will risk tearing the wrapper.

Ashing

People smoking good cigars like to keep the ash on for as long as possible. Indeed, a solid tower of ash is a sign of a well-made cigar. But don't let the ashy end grow too long - this is both pretentious and an invitation for a mess on the floor. Every once in a while, just gently press the ash against an ashtray - the ash should fall off easily without you having to tap the cigar. If your cigar goes out, it's okay. This does not mean you are a bad smoker - just remove the ash and re-light it.

Smoke the cigar for as long as you want - the only time you should stop smoking is when it stops being enjoyable for you. When that becomes the case, just set the cigar down in an ashtray and it will go out on its own. Do not grind it out, as that will produce excess smoke. Just take one last draw, set it down, take a sip of your drink, and revel in your smoothness.

5. STORE YOUR CIGARS

You may not realize this, but you're not supposed to smoke an entire box of cigars at once. Rather, you're going to have to store your cigars somewhere. This is very important, because cigars taste vastly better when they retain some moisture, so your goal is to prevent them from drying out:

  • Experts recommend storing cigars at about 70% humidity and 70 degrees Fahrenheit. Too cold and the cigars might dry out. Too warm and you may be greeted by tobacco beetles next time you bring that Corona to your mouth.

  • The most important thing when storing cigars is that they are airtight. Whether you keep them in a box or a plastic bag, try to keep the storage container tightly sealed.

  • Put a damp sponge in the box (or spray a little water into the bag). However, make sure that the sponge is not in direct contact with the cigars.

  • If you only have a few cigars left, you can buy metal tubes that are lined with cedar or leather cases. Again, just make sure that they are airtight.

  • If you decide to become a serious collector, consider buying a humidor. Humidors are special boxes in which you can keep your cigars, and they'll be much kinder to your stash than a plastic bag or standard cigar box. Humidors are usually quite attractive as well as functional, but be ready to pay at least $150 for a good one.

So now that you know how to choose, smoke, and store cigars, the only thing left is to join a cigar club, get a subscription to cigar magazine, and hope that your husband/wife/dog doesn't leave you if you take it too far. While smoking cigars is an expensive hobby to enjoy regularly, we strongly suggest that you save your newfound expertise for special occasions.