Choosing a Good Cigar: Beer and Cigar of the Month Club Subscription Giveaway

by Brett & Kate McKay on November 3, 2009 · 627 comments

in Manly Skills

Winston Churchill Smoking a Cigar

Editor’s note: This is a guest post from Andre Naser at To learn how to win a 3 month membership into their beer and cigar clubs, see the details below.

There was once a time when a man with a cigar in his mouth was held in high regard; a time when a young man toasted farewell to adolescence by igniting the end of a cigar that “just happened” to slip out of his father’s humidor. A time where the arrival of a man’s progeny was celebrated with cigars in the hospital’s waiting room.  A time when one could find a guillotine right alongside a man’s trusty pocketknife.

A 21-year-old Winston Churchill, on a quest to prove his manliness, ventured to the island of Cuba. It was in Cuba where Churchill began his love affair with the cigar. He described cigars as part of his “rule of life prescribed as an absolutely sacred rite; smoke cigars and drinking of alcohol before, after and if need be during all meals and in the intervals between them.” Churchill was so renowned for his cigar habit that a cigar of especially large magnitude still carries his name today: The Churchill cigar.

There can certainly be some intimidation when you first walk into a well-stocked cigar humidor. How can you possibly tell the difference between a Montecristo and an Ashton? Does it matter if this “Romeo y Julieta” came from the Dominican Republic and not Cuba? (why yes, it does). Fear not. After reading these quick tips on choosing a quality cigar, you’ll have an idea on how to pick a quality cigar. You’ll also be left wondering why you ever thought picking up a pack of Swisher Sweets from the gas station was a good idea.

Anatomy of a Cigar


The head: This is the end you put in your mouth. It’s sealed off and will require cutting; a guillotine is preferred to reduce the chance of smashing the cigar; however, a sharp knife will do. But for the love of God, do not use your teeth!

The foot: This is the side that you light.

The filler: A nice, consistent blend of dried and fermented tobacco.

The wrapper: The outside of the cigar. It varies in color from light to dark. A lot of the cigar’s flavor comes from this outer layer.

Choosing a Cigar

Now that you know your head from your foot, we can move onto choosing a cigar.  Check out a local cigar club.  They’ll likely have a well-stocked humidor and a knowledgeable tobacconist who will guide you through the selection.  When you arrive at the cigar club, you’ll walk into a humidor full of cigars. Humidors help maintain an optimal level of moisture inside the tobacco.  If it’s too humid, the tobacco will rot. If it’s not humid enough, the cigars will dry out and lose their flavor and aroma.

If this is your first time smoking a cigar, stay away from the higher-priced ones since, at this point, you won’t be able to truly savor the distinguishing elements of an expensive cigar. Besides, price isn’t the most most important factor in choosing a cigar. There are plenty of cheaper cigars out there that hold top ratings from major cigar publications.

While price isn’t that important when selecting a cigar, cigar construction and tobacco quality are. The cigar’s construction determines how smooth and even the draw is when you smoke it.  You can test the construction of a cigar by rolling it between the thumb and index finger of your hand. As you do this, make sure the cigar’s outside doesn’t have any lumps. Also check that the body is not too soft or void of filling. You want the cigar to have a nice even consistency and fill. A rough texture or any other mark of bad construction means a less smooth draw when you inhale.  With a well constructed cigar, the ash will maintain the shape of the cigar as it is smoked.

The second important factor when buying a cigar is the tobacco’s quality.  You typically can’t determine tobacco quality simply by looking at the outside of the cigar.  So how do you know which brands use good quality tobacco? It’s mainly based on reputation. Ask the tobacconist or your friends for recommendations on cigars that use quality tobacco. It’s usually a safe bet to go with larger brands. The big cigar brands tend to use higher quality tobacco in their cigars because they usually have first dibs on the quality stuff. In your quest to find cigars that use quality tobacco, just remember to purchase one cigar at a time instead of buying boxes. You don’t want to be left with a box of crummy cigars you’ll never smoke.

Now before you go running off to your local cigar club, let me first answer a question that typically comes up from those who want to learn more about cigars.

The Cuban Debate:  Are Cuban Cigars Really Better?

Cuban Cigars

I must first preface my answer by saying this: if you live in the U.S., don’t even bother trying to buy a Cuban cigar locally.  Because of a 1962 embargo against Cuba, Cuban cigars are not allowed in the U.S. (legally, at least). But because Cuban cigars are so desirable, a large counterfeit industry has popped up in the United States.  If someone says they have some Cuban cigars for sale, steer clear. It’s probably a fake and will leave your mouth tasting like charcoal when you smoke it.

You’ll also find clever Cuban immigrants rolling cigars claiming that since they themselves are Cuban, the cigars can be sold as “Cuban cigars.”  A clever scam, but a scam nonetheless. If you really want to smoke a Cuban cigar, you’ll either have to head north to Canada or south to Mexico.

Now to answer the original question: Yes, Cuban cigars are indeed better. Cuban cigars are highly regulated by the Cuban government and are held to a very high standard.  They’re also constructed by some of the most skilled cigar rollers in the world.  The “torcedores,” as they are referred to in Spanish, have been rolling cigars their entire lives, often learning the skill from family members who passed the knowledge on from generation to generation. The skill these workers employ ensures a consistent fill for the cigar every time.  The flavor of a Cuban cigar tends to be extremely overpowering to someone not acquainted with cigars.  They are much more full and smoky compared to their Dominican counterparts that tend have a more peppery and spiced flavor.

It All Comes Down to Personal Preference

The cigar-smoking experience is very personal. Everyone has different tastes, so make sure to try a few different varieties in order to discover your cigar of choice. It’s similar to finding your favorite beer. You probably didn’t know it was your favorite until you experimented with some different variations: more hops, less wheat, maybe some orange zest. But when you finally found your favorite beer, you knew it was the one. Cigars are going to be the exact same way.

And what if you could have a variety of cigars mailed straight to your door every month? Well, with the Cigar Of the Month Club you can try new and different cigars without leaving your house. It’s like the Fruit of the Month Club, but manlier.

The Beer and Cigar of the Month Giveaway

A 3-month membership to a cigar of the month and beer of the month club is up for grabs in this giveaway. One lucky winner will be getting a monthly shipment of 12, 12-ounce microbrews from two lightly distributed domestic microbreweries with a total of 4 different varieties to try. They’ll also get five professionally chosen, hand-rolled cigars from around the world. The focus each month is on quality cigars ranging from a variety of types. More information on the exact package can be found here.

How to Enter: To enter, simply leave a comment on this post sharing your favorite cigar brand, tip, or experience.

Deadline to Enter: The deadline to enter the contest is Monday, November 9 at 11PM EST. The winner will be announced on Saturday, November 14 in the weekly roundup.


  • Only open to residents of the United States (sorry, laws don’t let us ship alcohol and tobacco internationally)
  • Must be 21 to win.
  • Due to local laws beer can not be shipped to the following states: AK, HI, ME, and UT.
  • Adult Signature Requirements (Beer & Wine) – All beer or wine shipments are sent via Federal Express, UPS, or other local ground service carriers with an adult signature sticker required on the box. It’s best to have your shipments sent to a location where someone (21 & up) will be there to sign for it. Each carrier will make one or more delivery attempts and if unsuccessful they will leave door tags and/or phone messages indicating the attempted deliveries. Please respond to any communication from the carrier right away. After the final delivery attempt, the box is routed back to the local consolidation center closest to your shipping address and you may be given a short period to pick it up before it is sent back to our fulfillment center. We’ve intentionally packaged our shipments in a very non-descript, brown corrugated box such that most of our customers are comfortable having their shipments sent to their daytime location.
  • The memberships will be “gift memberships” which will automatically stop after the 3 months. They will be able to go online and easily continue membership on their own if they want, or let it expire without doing anything.

601 John Tullis November 8, 2009 at 5:56 pm

Favorite cigar is a Punch Rare Corojo. Pairs perfectly with a Cuba Libre.

Had two boxes of Punch at my wedding recently and they were all snatched up in about 10 minutes. Nice.

Would give anything to try a REAL Punch Punch from Cuba.

602 Michael November 8, 2009 at 5:57 pm

Best cigar moment was shared with a few friends on an overnight canoe trip. We cooked dinner by the river and sat around the fire smoking cigars. It has been so long ago that I cannot recall the brand. Good times, though.

603 Wes November 8, 2009 at 6:43 pm

Tip: Don’t make your first cigar something cheap, especially when a good cigar can be had for under $5.00. How will you know if you even enjoy cigars if you’re dropping a buck-fifty for a no-name drug store brand when you could spend just a few more bucks and get something that will reward you? And don’t even think of trying your hand at a pack of Swisher Sweets or some such.

604 Scott November 8, 2009 at 8:59 pm

My favorite memory of cigars was an epic, four to five hour dinner while I was in the Marine Corps. Five friends sat around a table of excellent food and fine wine and afterward smoked cigars while continuing the conversation long into the night.

605 Tommy K- November 8, 2009 at 9:08 pm

My first trip to the Carribean turned me on to the wonderful world of cigar smoking.
There is nothing like a good Arturo Fuente and 3 fingers of single barrel Carribean Rum-

606 Kyle Gilliam November 8, 2009 at 10:37 pm

My favorite cigar is a Macanudo Hampton Court. I first discovered this cigar while exploring downtown Anchorage while stationed there. A friend of mine stumbled into a small tobacco shop and into the humidor. We had no idea how to pick out a good cigar and only guessed when we walked to the counter with two Macanudo Hampton Courts. The store only nearly panicked when he saw us attempt to light them with a Zippo outside of his store. We were then schooled by the owner on the use of wood matches when lighting cigars.
While I have smoked better cigars and more expensive brands I still come back to this one for the memories.

607 Josh November 8, 2009 at 10:43 pm

Best cigar moment was on a cruise ship with my fraternity brothers. It was my first experience with cigars also.

608 Mitch November 8, 2009 at 11:52 pm

Smoking a cigar on the balcony, porch, or deck of a house or apartment during a mild summer night is a fantastic way to prolong a great day.

609 Steve M November 8, 2009 at 11:53 pm

I once had a Cuban Punch with a tall Erdinger on draft at a pub in Scotland. Best. thing. ever.

610 Eric H November 9, 2009 at 3:13 am

I don’t believe there is much better than smoking a Rocky Patel Vintage 1992 Torpedo with a draft Harp on the end of a summer night.

611 Brandon November 9, 2009 at 3:56 am

I dont remeber the brand, but my first cigar was one I had with my old man. I will always relish that day of my manly initiation!

612 Robin Whixx November 9, 2009 at 4:47 am

Cigar rolling is one of the famous art all over the world.Now a days it is considered as a part of entertainment.Most of the people enjoying the cigar rollers event as part of entertainment in parties and in marriages.

613 Steve G November 9, 2009 at 9:01 am

With my extremely limited cigar experience (only about 20 in my life), my favorite thus far is a Romeo y Julietta Romeo’s Court. I’ve only recently taken the plunge and began my serious attempt to become a true connoisseur. Obviously, this membership would go far in making that goal achievable.

614 Miles Chomel November 9, 2009 at 10:33 am

My buddies and I get together every two weeks or so to sit around our “smoke shack” (my cleared out garage with couches and a “manly” decor), and smoke cigars and tip back a few cold ones. Our choice of cigars are generally a more mediocre type. We always gaze at the expensive cigars when we are browsing through the humidor, but we always seem to revert to the cheaper ones due to our poor college studentness. Hence, why I would love to win the beer and cigar subscription of the month.

615 Dan Vining November 9, 2009 at 11:36 am

I toured the Leon Jimenes cigar factory in Santiago, Dominican Republic years ago and thus began my love affair with cigars. A truly wonderful event that allows a tour of the hand rolling area where cigars are crafted, followed by allowing tour members to enjoy a cigar with some fine Dominican Presidente. This is a right of passage for any man and something that stirs the echos of the fine men in history. I would love to pass this along as a gift to my brother in-law who has just welcomed into the world his three week old daughter, this would be a wonderful way to celebrate his journey as a man.

616 Nick Vadala November 9, 2009 at 12:29 pm

I’ve always been partial to Cohiba Coronas

617 Aaron L November 9, 2009 at 1:21 pm

I remember when I turned 18 I bought my first cigar, it tasted awful but I smoked it anyway.

618 Charles Jones November 9, 2009 at 1:58 pm

I enjoy the CAO Sopranos cigar. I’m sure it’s not the best, but I enjoy the branding.

619 Philip November 9, 2009 at 2:53 pm

My favorite cigar, thus far, is a Romeo y Julietta. Not too sweet, not too harsh… and it’s real smooth. My favorite cigar memory was when I was the best man for a friend’s wedding. After a night of shooting pool with the guys we went back to the house we were all staying at and made a bon fire. We then broke out an assortment of beer accompanied by a Romeo y Julietta and we roasted the man of the night.

620 Omer Duncan RN November 9, 2009 at 3:41 pm

I’ve been around the world. In War zones and Hot zones. When I left for Ft.Bragg in 83 my dad sent me out the door with a hand shake, some good advice “Be Good, Stay Alert” and a fist full of Partagas Padre Cigars. When I left Bragg my driver loaded my gear and I lit my cigar. “I did it dad”. My brothers and I have enjoyed a Partagas Padre Cigar in deep in the jungles of Panama, in the Euphrates river Valley in Iraq, and on the side of volcanos in Guatemala. He is with me every time I fire one up.

621 Chris Mitchell November 9, 2009 at 4:16 pm

Recently I have been enjoying a cigar comes from Don Kiki. Its a Churchill Limited Reserve Red Label which I find the best. It is aged for three years and has a nice and smooth flavor.

622 Stan Nusbickel November 9, 2009 at 5:10 pm

Davidoff is the best of the High End cigars that I have enjoyed, great quality and consistantly good. They have marketed their apprentice roller cigars under the Private Stock label, and these are fantastic and are quite affordable. They are made from 1st quality tobacco so you are able to enjoy a high end smoke for an affordable price….sort of like champagne tastes on a beer budget.

623 Mike Gottert November 9, 2009 at 6:30 pm

My favorite cigar experience… a guy I knew offered me a cigar almost every time a saw him, of course I took him up on it. One day I was on the street in front of his house and he invited me in to show me where he stored them. He had turned a closet into a walk-in humidor, it was if I had walked into a cigar shop. I still have no idea where he got them all.

624 Jeremiah Ellis November 9, 2009 at 10:30 pm

I had a good friend over who had always told me he loved to smoke a good cigar, so I pulled out some of my best that had been sitting in my humidor for almost a year, 2 Cohiba’s he proceeded to bypass the cutter and tried to bite off the end, and then after mutilating a fine cigar, he only smoked about a quarter of it before he left! No Shame!

625 Allen Martin November 9, 2009 at 11:46 pm

By no means is it the first or the most expensive cigar that I’ve had, but for unexplained reasons its my favorite: a Don Mateo. Its a dirt-cheap cigar thats good any day of the week, described to me as “a good smoke while mowing the grass.”

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