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How to Choose Your First Cigar: Best Cigars for Beginners

How to Choose Your First Cigar: Best Cigars for Beginners

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.

Table of Contents

Components of a Cigar

Start with Mild Cigars

What is a Good Cigar?

Don't Buy Junk

Learn with Affordable Cigars

Our Picks for Beginner Cigars

Beginner Cigars Sampler

Next: How To Smoke A Cigar

The Components of a Cigar

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 With Milder Cigars and Work Your Way Up

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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What is a Good Cigar?  

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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Don't Buy Junk

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 Smallbatchcigar.com.

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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Beginner Cigars Should Be Affordable

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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#1 Beginner Cigars: Undercrown Shade by Drew Estate

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 Notes: Cream, Pepper, Earth, Vanilla, Cedar, Nuts

#2 Beginner Cigars: Herrera Esteli by Drew Estate

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 Notes: Cream, Pastry, Cedar, Almond, Cinnamon

#3 Beginner Cigars: Luminosa by Crowned Heads 

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 Notes: Cream, Pepper, Wood, Caramel, Fruit

#4 Beginner Cigars: Rosado Sungrown by Arturo Fuente

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 Notes: Nuts, Exotic Spices, Cedar, Brown Sugar

#5 Beginner Cigars: Flor del Valle by Warped Cigars

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.

Tasting Notes: Cedar, Floral, Graham Cracker, Leather, Caramel, Citrus

Our Top 5 Cigars for Beginners Sampler

Sampler of our Top 5 picks for the best cigars for Beginners

Sampler including our Top 5 cigars for Beginners

Read Next: How to Smoke a Cigar


Frequently Asked Questions

Are cigars good?

We certainly think so!  Smoking a cigar is one of this life's finest pleasures, but it takes some searching to find your preferences and the cigars that you enjoy.  In fact, most of us are still trying to find our perfect cigar and just enjoying the ride until that day comes. 

What is the best mild cigar?

This is a frequently asked question that is categorically impossible to answer.  Since you're the only one with your taste buds, we can't say which cigar you'll consider the best out of many great options.  But we can say that the Undercrown Shade, Herrera Esteli, Luminosa, Rosado Sungrown, and Flor del Valle are what our customers tell us are their favorite mild cigars.  You can view our sampler here if you'd like to try them.

How much is a good cigar?

Cigars are like vehicles, you can always find winners in various price ranges!  Premium cigars usually cost between $5 on the low end and $30 on the high end, but we always suggest that you keep your search under $8 when first starting out.  This is because of diminishing returns, a phenomena where a cigar that costs twice as much will hardly ever be twice as good.  Most cigar enthusiasts would agree that $8 - $12 is the sweet spot for well crafted, satisfying cigars.  

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