Congratulations on deciding to smoke your first cigar! To help you get the most out of your first cigar, we’ve put together a guide on how to select the best cigars for beginners. Feel free to bounce around between the topics listed below in our Table of Contents.


Before we start talking cigars, let’s go over the basics: 

  • Body and Strength
  • Sizes of a Cigar
  • Wrapper, Binder, Filler

Cigars are often compared and contrasted by their body and strength.  Both body and strength are denoted as being mild, medium, or full.  Body refers to the depth of flavor, or intensity of flavors from a specific cigar.  Much like a full-bodied wine explodes in the mouth or a mild wine tastes watered down, the body of a cigar will determine how of it you can taste.  Strength, on the other hand, refers to the nicotine content of a cigar and impacts how you feel when smoking it.  

When you look online or visit your local Tobacconist, you’ll see cigars of several different types of sizes and shapes.  Typically, we list cigars by their length and ring gauge.  Length is measured in inches and ring gauge is measured by the diameter and effectively indicates the width of the cigar.  These measurements are then translated into common names that (with some flexibility) have an understood length and ring gauge. For example, the following cigars are usually close to these measurements:

  • Corona (5 1/2″ x 42)
  • Robusto (5″ x 50)
  • Toro (6″ x 50)
  • Churchill (7″ x 48)

Each cigar is comprised of wrapper, binder, and filler tobaccos to create a unique smoking experience.  Here’s an excellent example from Davidoff showcasing their Yamasa cigar:  

What is a Cigar: Wrapper, Binder, and Filler of a Cigar

Loose Filler tobacco is bunched together and held in place by a Binder before being finished with a Wrapper leaf.  Great care is taken in growing, selecting, and applying the wrapper leaf as it’s the visible layer of a cigar.  Your cigar may include tobacco from several different countries and regions as a blend is created by selecting multiple filler leaves, one or two binders, and a wrapper leaf.  

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Start your journey with a milder cigar until you know your preferences. You may find that you enjoy mild cigars overall, or you may decide that you are more of a medium-bodied or full-bodied cigar enthusiast. But choosing a mild cigar first reduces the chance that you will feel the negative effects of nicotine by smoking outside of your tolerance level.

Mostly, we want to ensure that your first cigar experience isn’t also your last! Smoking a full-bodied cigar may be appropriate for some, but also may turn others off to the experience. Cigars should be relaxing, satisfying, and pleasurable. Selecting a mild cigar first is like choosing to learn how to swim in a swimming pool versus being dropped into the ocean. You can learn the ropes without being overwhelmed.

Here are a few tips to identify a mild cigar:

  • Look for lighter wrappers (Connecticut Shade)
  • Ask your Tobacconist
  • Avoid smaller ring gauges (lanceros)

A Connecticut Shade wrapper refers to the color of the outside of the cigar. Connecticut shade wrappers are almost blonde in appearance (as pictured below) and are often an indication of a mild cigar.

Color of a Connecticut Shade Wrapper for Beginner Cigars

But remember, the wrapper of a cigar is just one of three components.  Experienced smokers enjoy a good surprise or deviation from normalities from time to time, but it’s likely not something that you’d appreciate as a beginner.  It’s always best to ask your Tobacconist if a cigar that you want to smoke matches your expectations.

When choosing your first cigar, we also recommend that you avoid some of the smallest ring gauges until you find your preference.  A smaller ring gauge will burn hotter, faster, and requires more technique to get the most enjoyment out of it. 

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The construction of a cigar can impact the flavor profile, maintenance, and overall enjoyment. When selecting your first cigar, it’s imperative that you choose something that has been crafted by a reputable factory.  And since flavor is completely subjective, the only real way to distinguish between a good cigar and a bad cigar is by how well (or not) the cigar was constructed.  Some headaches associated with a poorly constructed cigar are:

  • Constant touch-ups or relights
  • Unpalatable flavors
  • Poor draw or airflow

And headaches are exactly what we smoke cigars to get away from. A well-constructed cigar shouldn’t require babysitting it with a lighter to keep it burning evenly, nor should it require any additional relights. Your cigar should be the most relaxing thing you do that day.

Picture of a Man rolling a Cigar

Likewise, cigar enthusiasts try to avoid applying any more heat to their cigar than necessary. Each use of the lighter has a chance of altering the flavor profile. Your cigar won’t taste as appetizing if it’s burning hotter and faster.

Each of the cigars that we’ve featured in our Beginner Cigars Sampler below is a classic cigar from some of the most well respected manufacturers and brands. We don’t want your first cigar (or cigars) to feel like you’re trying to drink a frozen McDonalds milkshake, nor do we want the experience to be overshadowed by gripes and complaints. We want your first cigar to be memorable in all the right ways.

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As you’ll see below, we don’t want you to spend a lot of money learning the basics of cigar smoking. But, we also don’t want you to waste your money buying junk. Here are a few things you can avoid to make sure that you aren’t buying junk: 

  • The gas station
  • The PX/BX/MCX/NEX (Military Exchange)
  • Moldy cigars

Now, when talk about cigars, we’re talking about premium cigars – not the stuff you see at a gas station in a box for $3.99. In particular, Black and Milds are often referred to as cigars in conversation (and labeling) but aren’t considered real cigars. In general, premium cigars won’t be found at a gas station. Look for the good stuff at your local Tobacconist or

Buying cigars at a military exchange is usually a bad idea. Almost every single AAFES humidor is under humidified (usually isn’t even closed all the way) and will only result in disappointment. If you purchase a cigar at a military exchange, expect to have to carefully rehydrate your cigars for months afterward before being able to fully enjoy them. The one exception would be cigars such as the Southern Draw brand that are sealed in high-grade plastic with a Boveda pack so that they’re kept fresh regardless of the store’s neglect.

Picture of an under humidified humidor in an AAFES store

Picture of a military exchange humidor taken on the publish date of this article. Hygrometer reads 34% humidity, most cigars should be stored between 65% and 69% humidity.

Lastly, local shops tend to keep their humidors over humidified to adjust for the walk-in humidor being opened and shut several times throughout the day. This isn’t a bad thing, but without proper inspection and care a humidor can become moldy. Mold will then appear on the wrapper and foot of cigars and is unhealthy to smoke.  Do not buy or smoke moldy cigars! 

Here are some telltale signs that a cigar has mold on it:

  • You can see spores
  • The substance in question is splotchy
  • It isn’t crystalline
  • It may be multi-colored
  • It is raised off the wrapper
  • It photographs well
  • There are other cigars from different boxes with the same substance
  • If the substance is on the foot of the cigar, it is definitely mold

Less reputable shops will claim that the mold is plume, a phenomena that is a sign of a well-aged cigar. But you have a better chance of being struck by lightning while driving to pick up your winning lottery ticket than seeing plume in a retail establishment.

Actual plume is so rare that most of the people who write about it are just regurgitating information that we heard from another source. It may not even exist. But if it does, here’s what it should look like according to the Cigar Bible:

  • The substance would cover the wrapper uniformly (not just the head)
  • It’s crystalline in nature
  • There it photographs poorly
  • Cannot be multicolored
  • Cannot be on the foot
  • Is very rare and would not be a multi-box occurrence

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One of the classic blunders of budding cigar enthusiasts is to jump head first into the hobby with lots of cash. We suggest that you use your first cigars as a learning experience without fronting the cost for an Ivy League education. Why? Because mistakes will be made and cigars will be sacrificed.

If you’d like to get a headstart on learning how to smoke a cigar and avoiding classic mistakes, we’ve got you covered:

Buy Cheap Cigars When Learning How to Smoke

There are plenty of cost effective cigars out there, but we suggest that you limit your search to $8 or less. And, when you’ve become a fully-fledged Cigar Aficionado, you’ll probably find that $8-$12 is the sweet spot for a lot of great smokes anyway.

We also suggest that you start with singles or samplers when you’re first starting out. Not only does this reduce the cost of your investment, it also allows you to sample more cigars in turn to find which strike your fancy.  Finding your personal preference is all about trying new things, and in this case you have to Burn to Learn.

Every sampler pack like the one you’ll find below includes a high-grade plastic bag and a Boveda pack to stabilize humidity. This means that you can safely and comfortably store your cigars inside the package that we ship you for 4-6 weeks with regular use. Save the humidor choices for once you’ve learned which cigars you’d like to stock it with.

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Best Cigars for Beginners: Number 1 Drew Estate Undercrown Shade

The Undercrown Shade is often recommended as a first cigar because of the smooth, creamy texture and subtle flavors offered by a Connecticut shade wrapper.

Tasting NotesCream, Pepper, Earth, Vanilla, Cedar, Nuts


Best Cigars for Beginners: Number 2 Herrera Esteli

Willie Herrera, the same Gentleman that blended the Undercrown Shade, blended the Herrera Esteli to bear his namesake. His blends are known for their creamy texture and rich flavor without overwhelming the palate.

Tasting NotesCream, Pastry, Cedar, Almond, Cinnamon


Best Cigars for Beginners: Number 3 Crowned Heads Luminosa

The Crowned Heads are well known throughout the boutique cigar industry for producing a variety of flavor profiles. Luminosa steps into the mild-medium range to provide consistent flavors that will have you coming back for more.

Tasting NotesCream, Pepper, Wood, Caramel, Fruit


Best Cigars for Beginners: Number 4 Arturo Fuente Rosado Sungrown

If you ask someone about affordable cigars, beginner cigars, or celebration cigars, chances are that you’ll be recommended something by Arturo Fuente. Produced in the Dominican Republic, the Rosado Sungrown is a timeless classic that never disappoints.

Tasting NotesNuts, Exotic Spices, Cedar, Brown Sugar


Best Cigars for Beginners: Number 5 Warped Flor del Valle

Note: We may have to substitute a different cigar due to availability.

Last but certainly not least, the Warped Flor del Valle merges new world blending techniques with old word tradition. Flor del Valle is a true medium-bodied cigar that serves as the perfect introduction to Warped Cigars in general as well as stronger cigars.

When selecting a cigar for the first time, it can be seen as a very daunting experience. You’re in a foreign place with many different cigar brands, sizes, names, and colors; you quietly think to yourself what does all of this mean? The best thing to do at this point is taking a breath and let the guiding hand of a tobacconist help you, but in order for him or her to help a bit of information will be needed at first. So let’s start…

So before you take that stroll into your local shop, let’s go over the very basic information you will need to know…

Cigar Profile

The first question you will be asked is “What strength cigar would you like?”

To start with, you need to know that there are 3 basic strength classifications.

  1. Mild
  2. Medium
  3. Full Body (Strong)

Much like the cook on a meat (where the basic cook can be rare, medium or well cooked), these classifications can often be broken down further to incorporate strengths that will bridge the gap between the major classes.

These expanded classifications will now include:

  • Mild
  • Mild – Medium
  • Medium
  • Medium – Full Bodied (Strong)
  • Full Bodied (Strong)

If you never smoked a cigar, or any tobacco product it’s pretty safe to say that you probably would want to start out with a mild cigar. At least that is what I would recommend until we would find out how your enjoyed your first cigar. Here is a great list of beginner cigars that offer a exceptional flavor and a very mild and smooth smoke. Montecristo White is a great beginner cigar, so is Macanudo Café. Another great choice is the Licenciados Toro which received an outstanding 93 rating by Cigar Aficionado magazine. If you’re a bit of a high roller try a Davidoff for a more exquisite cigar.

In my personal opinion if you just enjoy smoking; I believe that there is a cigar for you, we just need to find the right on for you to try. I personally smoked a number of cigars before I got into cigars. It was a Hoya De Monterrey Epicure #1 (a Cuban) what started me on my cigar adventure, but I wouldn’t enjoy it today as a more seasoned smoker. Unless well read the examples below.

If you’re a more seasoned smoker and have enjoyed a couple of cigars, and are able to smoke a medium – full bodied cigar. There are exceptional cigars like Flor De Las Antillas Maduro which is the maker of the #1 cigar of the year blend of 2012, in a maduro wrap. Also a Cohiba Macassar (one of the best tasting cigars outside of Cuba), The Bauza by Arturo Fuente or the Davidoff Yamasa which is amazingly smooth but really full bodied, with a complex smoke.

Another thing we really need to think about is the who, what, when, where of enjoying a fine cigar would entail. I’ll use a few examples.

how to choose a cigar

Example 1: The Golf Course

Let’s say you want a stogie for the golf course and tee time is about 11am, and it’s going to be a pretty warm day even a hot day. I would suggest smoking a mild cigar at most a mild – medium smoke. So the aforementioned Macanudo CaféMonte WhiteLicenciados or Davidoff would be a great cigar to enjoy while hitting the back 9.

how to choose a cigar for dinner

Example 2: Dinner

Now you would like an after dinner smoke, you’re going to eat an amazing steak dinner probably have some wine along with your meal and finish with a coffee or a nice cognac after eating. Anything from a medium – full bodied cigar would be great to compliment a big dinner, especially if ending with a coffee or fine cognac or scotch. This would pair perfectly with the Davidoff YamasaCohiba Macassar, Bauza or Flor De Las Antillas Maduro. The strength and complexity will compliment your evening extremely well.

Choosing a cigar size

Since were dialed into what strength of cigar we would like to smoke lets choose a size that is right for you. Some guys enjoy smoking for hours, others enjoy smoking for 45 mins or even 20 mins and under. Size as well a strength is a matter of personal preference, but no matter your preference your environment will differently play a factor.

Let’s revisit the examples above to gain some clarity.

how to choose a mild cigar

Example 1

Let’s say the person at the golf course who we recommended a mild cigar to also said they have a long round of golf and wanted to smoke for a few hours. I would suggest a minimum size of a Churchill, and would even recommend a double corona for an extra-long smoking time. This is something that he can take to the course light up and smoke for about 2 hours or more depending how it’s being smoked. Ensuring a consistent flavor and strength not throwing off our golfer from beating his handicap.

how to choose a maduro cigar

Example 2

For the after dinner smoke basically you have as much or as little time that you allow yourself or may be what your wife allows you. For argument sake let’s say you have only about 45 mins and you also choose a pretty full bodied cigar we should probably limit your to a robusto size, or at most a Toro size cigar. The size is important. I feel like the last 3rd of the cigar is the best (that up for argument a lot of people agree and disagree) but, we can all agree that wasting a cigar is a sin! So let’s not be over ambitious in our smoking get smoking that you could enjoy right down to the end.

Remember, despite what you may have heard, size matters. Personally, I feel like the last 3rd of the cigar is the best (although that’s up for debate as many people agree and disagree with this statement). But we can all agree that wasting a cigar is a sin! So let’s not be overly ambitious in our smoking and be sure to choose a cigar you can enjoy right down to the very end.

Picking the Actual Cigar

Now that we know the strength and size of the cigar, you should now have the box in front of you to choose from. When selecting the cigar make sure it looks good to you, there can be slight wrapper color variation with in the same box so don’t be alarmed just pick what you like! Ensure that the wrapper looks flawless, if not flawless just make sure you like it (I choose cigar out of my humidor with bad wrappers to smoke first because they won’t last long in the humidor depending on wrapper damage).

Now that you found a cigar that looks good. Take it out gently and hold it firm, but not to firm (you don’t want to press hard on the cigar at all). Feel the cigar gently and give it an ever so slight squeeze, feel up and down the cigar gently to see if you will get a good draw. Your feeling for plugs in the cigar it could be much more firm than any other part of the cigar.

Be careful of the head of the cigar do not press to the top because you can crack the head and ruin a perfectly good cigar. The cigar should have a little spongy feel. Once you found the one to smoke you’re ready to enjoy your cigar.

Congratulations! You have found your perfect choice and are ready to enjoy your cigar!

Comment below and share how you choose a cigar.

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