Cigars 101

5 Important Questions You Should Ask Before Buying A Cigar…And One You Shouldn’t


Updated July 2023

Maybe you’re thinking about buying your first cigar. Or maybe you already have and were disappointed with the results. In either case, the prospect of diving into the world of premium tobacco can feel overwhelming. There are so many different cigars, so many things to know, and unfortunately, so much misinformation.

Not to worry.

I learned the hard way; you don’t have to. Get everything you need up your sleeve to choose and checkout with confidence inside this simple guide.

Remember, smoking cigars is supposed to be relaxing and rewarding—not an anxiety-inducing chore. Ask these 5 questions before purchasing a cigar and you’ll be on your way to smoking bliss!

As a bonus—remember when they said there’s no such thing as a bad question? Turns out there is. On top of the 5 Questions to Ask Before Buying a Cigar, I’ve included a question that nearly everyone asks, but shouldn’t. Read on to find out why!

Question 1: What is the best cigar for a beginner?

cigar advisor 5 things you should ask before buying a cigar - question 1: what is the best cigar for a beginner?

Your best bet is something with a mellow body. By body, I mean the intensity of the blend’s flavors. Cigars with mellower bodies typically have gentler flavors like cedar, nuts, leather, and toast, and avoid heavy peppers or spices. The formula for such a cigar usually involves mellower tobaccos—including the popular Connecticut wrapper.

Most cigar manufacturers have a mellow blend among their offerings, but first-time smokers are typically steered toward brands like Macanudo, Arturo Fuente, and Romeo y Julieta due to their time-tested success with giving a tasty initial impression.

Discuss what you like and dislike in food and it will help your tobacconist steer you in the right direction. Below, you’ll find the most popular mellow cigar at Famous Smoke Shop.

Lauded for its effortless draw and silky-smooth flavors of cedar, earth, leather, and vanilla, Romeo’s House of Capulet is loved by newbie and veteran smokers alike.

Question 2: How many cigars should I buy?

cigar advisor 5 things you should ask before buying a cigar - question 2: how many cigars should i buy?

When you’re shopping for cigars, you’ll find that they come in boxes, bundles, 5-packs, samplers, and singles. Not exactly short on choices there, are you? I’ll narrow them down to two for your first buy.

Go for a 5-Pack or a sampler.

One of the most common newbie mistakes is to buy just one cigar. You take it home, light up, smoke it, and realize, ”this is terrible.” Maybe it’s not the right cigar. Maybe it’s the right cigar at the wrong time. But you’ll never know…because you don’t have any more.

You’ll know after smoking at least 2-3 cigars whether it’s the right blend for you. In addition, smoke the second cigar at a different time of day. It may not be the cigar that was off, but possibly your taste buds instead.

So, maybe you went back and forth with your tobacconist and couldn’t land on the right cigar to try. The next best option, if he hasn’t already suggested it, is a sampler. Instead of one cigar to try, you get several at a discounted price. Here’s a mellow cigar sampler, ripe with easygoing premiums for FNG smokers:

This who’s who of mellow cigars features critically acclaimed brands like Macanudo, Rocky Patel, Gran Habano, and more. Each is wrapped in a Connecticut leaf to ensure a satisfyingly creamy smoking experience.

Question 3: When is the best time to smoke a cigar?

cigar advisor 5 things you should ask before buying a cigar - question 3: what is the best time to smoke a cigar?

Answer: It depends on the cigar you’re smoking. If you took my advice and started with a mellow blend, there’s not really a ‘wrong’ time to smoke it. Just keep in mind—even mellow cigars are going to feel a little stronger to you at first. My advice would be to wait until after lunch or a light dinner.

You’ll get to a point where you can even pair mellower cigars with your morning coffee, but they may be a little too harsh for your palate in the early hours. It’s why Question 2 is so important. Your cigar experience varies by the time you’re smoking it. Having a few on hand to narrow down the best time for you is a good idea.

Question 4: How much should I spend on a cigar?

cigar advisor 5 things you should ask before buying a cigar - question 4: how much should i spend on a cigar?

The biggest cigar lie: the more you spend, the better they taste. Stop believing it. You should—as you always do—purchase within your budget. Are you a billionaire? Who cares. Buy whatever you want. Buy the entire factory. For the rest of us mere financial mortals, there are great cigars (under $10…even under $5). There’s no need to spring for a luxury-class smoke right off that bat.

You wouldn’t learn to play violin on a Stradivarius, right? Step your way up slowly.

But if nothing I’m saying will sway you from the ‘you get what you pay for’ mentality, here are some high-roller cigars worth splurging on for your first time—even if I don’t personally agree with such a plan.

Question 5: How do I keep my cigars fresh once I’ve purchased them?

cigar advisor 5 things you should ask before buying a cigar - question 5: how do i keep my cigars fresh once i've purchased them?

If you’re planning on smoking what you’ve purchased within a week or two, you’re better off not fretting about your cigars’ home care. Nevertheless, knowing a few basics will help you hit the ground running. As the adage says…”an ounce of prevention is worth a pound of cure.”

Cigars are a natural product and don’t contain preservatives. As such, they have humidity and temperature requirements that keep them fresh over the long haul. A good rule of thumb is 65-70% humidity and 70 degrees.

Temperatures and humidity that climb higher can cause burning issues, poor flavor and draw, and even promote mold growth. If humidity and temperature fall too low, your cigars can dry out and crack.

Again, don’t worry too much about this if you’re smoking just one or two cigars. Even a 5-pack. Keep them in a resealable plastic bag and you’re fine. Getting a proper handle on cigar humidification will come later. We have a guide for that, too.

Last but not least…

What NOT to ask when buying a cigar: “Is it good?”

cigar advisor 5 things you should ask before buying a cigar - bonus, what not to ask when buying a cigar: "is it good?"

Not only is asking “is this cigar good?” a loaded question, but it also means different things to different people. None of the answers you’ll get will necessarily reflect the experience you’ll have.

A tobacconist might answer the question from the perspective of his palate. If he loves the cigar in question, you may be inclined to buy it. But what if his favorite food is pickles—and you think they’re disgusting? That could spell a cigar purchase ending in buyer’s remorse.

A fellow smoker, on the other hand, might answer it solely based on the brand’s popularity—or lack thereof.

You’re better off asking an open-ended question to prevent a simple “yes” or “no” response. Try wording it this way: “What do you like about the cigar?”

With a question framed this way, expect to hear about flavor and complexity. Maybe draw and construction. You’ll get a list of what impressed him, instead of an obligatory “it’s good.” And while we’re on the subject, ask what he didn’t like, as well. Any tobacconist worth their salt won’t hesitate to tell you the cons as well as the pros. Ignore those who just provide lip service.

Hope you found this guide helpful. Let me know in the comments the questions you’ve been asking before buying cigars!