Cigar smoking isn’t for everyone. We know that. But we still think every man should know a bit about the art. There’s a lot of history behind this age-old practice as well as an entire culture to go along with it. Plus, you wouldn’t want to seem foolish when one of your friends eventually has a baby and passes out cigars to all of his friends. Would you?


Here’s our very basic beginner’s guide to smoking cigars along with some history, tips and tricks. It’s always nice to cut the cap off of a nice cigar, pour a glass of whiskey and relax at the end of the day. Give it a try. No pressure.

It’s easy to say that Christopher Columbus discovered cigars. However, like America, cigars were around way before Columbus supposedly discovered them. Instead, it’d be more accurate to say he simply helped introduce cigars to mainstream culture.

Truthfully, the famous explorer and his sailors witnessed local natives in the Caribbean rolling up and smoking dried up tobacco leaves, which were foreign to the explorers at the time. They enjoyed smoking these primitive cigars so much that they loaded up on the substance and returned to Spain. Soon enough, cigar-rolling techniques were perfected, and cigar smoking spread throughout the world.

Eventually, cigar smoking became a wildly popular activity among men in the early 20th century. Masculine men such as Babe Ruth and John Wayne were continually depicted in the media smoking cigars. Orson Welles intentionally wrote cigar-smoking characters into his films, and it’s said that Mark Twain smoked as little as 22 cigars a day. He was supposedly quoted as saying, “If smoking is not allowed in Heaven, I shall not go.”

Over time, cigars became Cuba’s main export, and we all know how that worked out. Because of Fidel Castro and the impending Cuban Missile Crisis, John F. Kennedy authorized a trade embargo with Cuba in 1962, making Cuban cigars illegal in the United States. However, Kennedy, the sly cigar lover, had his press secretary order 1,200 hand rolled Cuban cigars just hours before the embargo was authorized. Cuban cigars are still illegal in America today…so don’t buy them.


The method by which they are made is the easiest way to categorize cigars since there are only two groups: hand-rolled and machine made.

Hand-rolled cigars are the preferred choice for beginners and connoisseurs alike. Machine made cigars such as Dutch Masters may contain preservatives and chemicals whereas hand-rolled cigars are made with pure tobacco. The filler in hand-rolled cigars as well as the binder to hold the filler and the outer wrapper are all made from 100% tobacco leaves.

Additionally, cigar tobacco is grown in several places around the globe, but some of the highest quality tobacco Brazil, Cuba, the Dominican Republic and Honduras. Generally speaking, tobacco in hand-rolled cigars tastes better than that of machine made cigars. Plus, who really wants to taste a grape flavored cigar anyway?


Hold on there. Before just jumping into cigar smoking, find a nice, mild cigar to start with. Some cigars may be a bit too strong for beginners and may ultimately ruin the entire experience. Mild-flavored cigars are also slightly cheaper, which may make it easier to ease into the hobby. You also won’t have to worry much about lighting an expensive cigar incorrectly or cutting off too much of the cap of an expensive cigar.

Once you’ve decided on your cigar, inspect it for any imperfections. Check the wrapper for cracks or discolorations, and search for any hard or soft spots by gently squeezing the cigar. Soft spots may indicate your cigar has less tobacco in it than you’re going to want. Hard spots may indicate that the cigar has been packed too tightly and may result in a plugged cigar, making it hard to smoke. Although many seasoned cigar enthusiasts would rather replace the plugged cigar, massaging the plugged cigar to get rid of the plug can sometimes alleviate this issue.


Initially, we wouldn’t recommend heading out and purchasing a humidor immediately, as you may still be easing into the art of cigar smoking. Just don’t buy more cigars than you can smoke within a few days, and keep them safe in their cellophane packaging or a Tupperware container to prevent them from drying out. A dried out cigar burns quicker, loses its flavor and will peel or crack more easily.

However, if you plan on committing to this age-old past time, a humidor is a must. A humidor is a box-like piece of furniture, or even an entire room, that optimizes the humidity surrounding your cigars. Essentially, humidors keep your cigars fresh and worthy of smoking for an extended period of time.

However, a decent humidor can cost between $50 and $200 or more. If this is too steep for your budget, some tobacco shops sell humi-pouches, plastic bags with a humidified lining. These pouches are available in a variety of sizes and can keep your cigars fresh for up to 90 days.


If you don’t have a cigar cutter, biting the cigar with your teeth should be the absolute last thought on your mind. Using scissors or a sharp knife will work better, or you could just poke a hole in the end of the cigar. This will provide an acceptable passageway between the tobacco and your mouth without unraveling the cigar or getting bits of tobacco in your mouth.

That being said, buy a cigar cutter. This is the easiest way to provide the best smoking experience. There are a lot of different styles of cutters and ways to cut your cigar, but we’re going to simply recommend using a straight cut on your cigars with a guillotine cutter, the most common way to cut your cigars.

Holding your cigar and your cutter in each hand, insert the head of the cigar – the closed end – roughly an eighth to a sixteenth of an inch into the cutter. Then, simply cut the cap off. Avoid cutting into the body of the cigar, as it will cause your cigar to unravel.


For the best cigar smoking experience, use butane lighters or wooden matches to light your cigar. Never use candles to light your cigar, especially scented ones. This can ruin the quality of your cigar. Also…a scented candle? Come on.

While lighting, without inhaling, puff and rotate your cigar while holding the flame just below the other end of your cigar. Be careful to not let your cigar actually touch the flame, let the heat from the flame to do all the work.

Continue this process until the tobacco around the outer rim your cigar begins to glow from the heat. The smoke should be easy to draw at this point, and you should be ready to enjoy your cigar. Keep the lighter or matches handy in case you accidentally let your cigar die out.


Again, do not inhale the smoke. Trust us, you won’t like it. Allow the smoke to fill your mouth, taste it and blow it out. Continue to puff and rotate your cigar every once in a while. If you smoke it too fast, your cigar will burn fast and ruin the flavor. If you smoke it too slow, you’ll have to continually relight it. Flick the ashes once they’re down to about half an inch.

You may also want to choose a drink to accompany your cigar. Although we’ll always recommend whiskey – Scotch is the preferred whisky among cigar smokers – coffee drinks, martinis and Indian Pale Ales pair well with the full flavor of your cigar as well.

Once you’ve picked out your preferred cigar, pour your favorite drink and put on some relaxing music. You may find that, health problems aside, cigar smoking can be an extremely tranquil way to pass the time.