Everything you need to know to buy and smoke a high-quality cigar like a pro

Cigarettes, cigars, smoke shop, Nat Sherman 2444Sarah JacobsSmoking a cigar correctly is an art. Start with a tobacconist to guide you to the right purchase.

Once a mark of status akin to the shoes you wore or the watch on your wrist, cigars today are — for most of us — more a hobby than a lifestyle. You’ve probably smoked one at special events or celebratory occasions, but do you know how to smoke one properly? And can you tell the good stuff from lower quality?

Turns out, cigars are a lot like wine: complex, full of variety, and with a whole world of rituals to discover. We spoke with Michael Herklots, vice president of brand and retail development of the historic Nat Sherman cigar brand and certified retail tobacconist, to learn more. Herklots has been working in the world of tobacco for decades, and is an expert on the subject.

Below, find his advice on how to approach the world of cigars with the knowledge you need to make sure you’re getting the best experience.

What kinds of cigars are out there?

Sarah Jacobs
Inside the Nat Sherman Townhouse humidor, hundreds of kinds of cigars are on display.

Like food or wine, Herklots says, the variety is endless. 'Where do you begin?'

'Premium' cigars come in a countless combination of shapes, sizes, and origins, with an infinite number of tobacco ages and species. They can be mellow and creamy or full and spicy, short and fat, or any variation of the above.

In Herklots' opinion, the greatest quality premium cigars today are being made in the Caribbean, Central America, and Mexico, using tobaccos from around the world.

Where can I buy a cigar -- and where can I smoke it?

Sarah Jacobs
Finding a social space to smoke can be a challenge. In the Nat Sherman Clubhouse, members lounge in the basement.

You can learn about and buy cigars online or at smoke shops or specialist tobacconists. But where to smoke them? With anti-smoking regulations clamping down across the country, your best bet (besides the great outdoors or the comfort of your own home) is a dedicated smoking parlor.

'Perhaps one of the things that make the tobacconist so special -- besides the fact that enjoying cigars is almost never allowed indoors -- is that you're able to engage with the employees of the tobacconist who have chosen to make their hobby a profession,' Herklots says of the smoke shop experience.

'No other place brings together lovers of the leaf the way a tobacconist does.' In Manhattan, the Nat Sherman Townhouse near Grand Central Terminal is one prime spot to settle in with a cigar.

How can I tell a good quality cigar from a poor quality one?

Sarah Jacobs
Cigar quality can vary widely. 'Premium' cigars are entirely handmade.

A few factors separate a premium cigar from something of lower quality. Premium cigars are made entirely by hand, and use 100% long-filler tobaccos, meaning the leaves on the inside of the cigar run its entire length. The three primary components are filler tobaccos, a binder, and a wrapper; if a cigar doesn't have these three things, it's not premium.

Cigars should be stored at the right temperature and humidity (70 degrees Fahrenheit with 70% humidity is what you should aim for), keeping it in condition to smoke.

'At the end of the day, a good cigar is one you enjoy,' Herklots said. A lot comes down to taste and preference.

What flavours should I be looking for in a cigar?

Sarah Jacobs
A tobacconist at Nat Sherman removes a cigar for a customer.

Like wine, tasting cigars requires experience and a specific vocabulary to define the complex flavours. But ultimately -- also like wine -- a cigar will taste like the land the tobacco was grown in.

On the flavour side, you can find notes of breads, nuts, and woods (toasty, roasted almond, charred oak, etc.); you can find spices (clove, cinnamon, cardamom, white pepper, black pepper, etc.); and you can find other elements, like coffee or cocoa.

As you smoke, it's also important to identify how the cigar feels. Does it make you salivate, or does it dry your mouth? Is the smoke light or heavy, hot or cool, silky or creamy?

'The relationship of strength, flavour, aroma and combustion are the four pillars we build an experience on, and the flavours and feelings play a key role in that analysis,' Herklots said.

What's the right way to light a cigar?

Sarah Jacobs
Your lighter should be scentless, so it won't interfere with the flavour of the cigar itself.

Step one: cut the cigar properly.

'In order to taste the cigar in the manner the manufacturer intended, it's important to execute a full, straight cutting style using a double guillotine cutter,' Herklots said.

Step two: take a few puffs without igniting it. Called 'dry' smoking, it allows you to tell if the cigar was stored well and that the tobaccos were processed correctly. If something's wrong, you'll taste mildew, mustiness, or ammonia.

Step three: light the cigar using a non-aromatic flame. Cigars light by heat (not intake), so you can hold the cigar in front of you and place the flame below the open end (that you didn't cut -- called the ''foot'), rotating it until it begins to smoke and glow. Then blow gently on the foot or wave the cigar, so that air stimulates it to light fully.

Step four: once the edges are lit, go ahead and take a puff -- and bring the heat closer to the foot as you do.

What's the right way to smoke a cigar?

Sarah Jacobs
Pro tip: don't inhale, just hold the smoke in your mouth.

Everyone has a story about a cigar-smoking experience gone wrong. Because unlike smoking a cigarette, a cigar is not meant to be fully inhaled.

'A premium cigar is never intended to be inhaled, but rather enjoyed within the mouth and nose,' Herklots said. 'Enjoying a cigar is like drinking through a straw.'

It's the same principle as the straw: draw slowly through the cigar, but allow the smoke to stop and 'rest' on your palate. Then, expel the smoke from your mouth.

'As a tip -- take a breath and hold your breath prior to puffing … though awkward, it will prohibit you from being able to inhale,' Herklots said.

How do I properly store my cigars?

Sarah Jacobs
This old-fashioned antique humidor will keep cigars fresh.

You want to keep your cigars at 68-70 degrees Fahrenheit with 68-70% humidity, which helps preserve the essential oils in the tobacco and controls combustion. If tobacco gets too wet, it won't burn; if it becomes too dry, it will burn too fast and too hot.

A humidor is the best way to ensure proper storage; humidors can be anything from elaborate wooden boxes to full rooms with temperature and humidity control. For the lower-key cigar enthusiast, even a ziploc bag, cooler, or refrigerator will do the trick with a little bit of attention.

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