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.

501 Dan Clark November 4, 2009 at 5:34 pm

A few thoughts on the subject of cigars

Golf course cigar – Hoyo de Monterrey Excalibur No. 1 7.2 x 54 Maduro large enough to get through six holes maybe nine depends on pace of play.

Lawn tractor Cigar – The CAO America 5 x 56 what is more American than cutting grass and smoking a cigar.

On the deck grilling/relaxing – Maker’s Mark Robusto 6 x 50 strikingly delicious great smell

502 Joseph Sarreal November 4, 2009 at 7:11 pm

Without a doubt, my favorite cigar is the Padron 6000 Maduro.

503 Chris November 4, 2009 at 7:18 pm

My most memorable cigar experience was smoking an early 1995 Lewinski. It was well aged with perfect aroma and flavor. It contained the thrilling scent of scandal.

504 Matt November 4, 2009 at 8:07 pm

My old college room mate, who was also the best man in my wedding, is serving in the air force now. We usually make a point to smoke a cigar whenever he visits. The sad part of the story is that he is satisfied with the “cigars” available at the gas stations. I’m going to see if I can’t break him of that the next time he visits. Surprise him with a real cigar!

505 Biggyrat November 4, 2009 at 8:18 pm

Shortly after discovering the joys of a fine cigar, my sister-in-law and her husband came to visit us for Christmas. They live in Chile. The husband handed me a box of Romeo y Jullietta petite coronas, with the Habanos label affixed accross one corner. They were some of the best puros I have ever enjoyed. I have heard that they are hand rolled along the inner thighs of virgins. Truely a fine smoke.

506 Garrett November 4, 2009 at 8:24 pm

My absolute favorite is a Red Lion Colorado Maduro. My buddies and I would enjoy these almost nightly while deployed in Iraq. It was a 30-40 minute break from the unpleasant reality around us. They are strong and spicy cigars. Like smoking a Cigar dipped in Tabasco.

507 Al November 4, 2009 at 8:47 pm

I seemed to have always done well with the Punch line, specifically their Robusto Maduro cigar. Personally I enjoy a pipe a bit more.

A great tip is to be slow about smoking a pipe/cigar. It isn’t going to burn quickly like a cigarette, and the flavor will be much more appealing. It is not uncommon to have to relight a cigar/pipe a handful of times during a smoke (and is often a good indicator of conversation).


508 Jason November 4, 2009 at 8:59 pm

I was “brought into manhood” with my first cigar about a year and a half ago. It was a Padron. I still remember that evening in the cigar bar with a beer in my hands and a smoky haze throughout the room. Ever since then, I have continued to go back to the Padron…sometimes I enjoy the natural, and other times I’ll enjoy the maduro.

I have also gotten a taste for the Romeo y Julieta, particularly the maduro.

Because society’s standards have changed since the Churchill days, it is not as easy to enjoy a good cigar. One now has to either build a ventilation system in the home/work office, go to a cigar bar, or enjoy a smoke on the patio at home. Option one is unpractical for most. Depending on where you live or the freedom of your time throughout the day (ie. family man), option two can be limiting. And as for smoking on the home patio, it only works when the weather isn’t freezing or scorching. Oh for the days of Churchill!

P.S. When I grow up, I want a job like Rush Limbaugh where I can work and smoke a cigar at the same time. What a gig!!!

509 mack November 4, 2009 at 9:34 pm

Me and a buddy were at a fiber optic training class in Cincinnati just prior to be deployed overseas. We were setting on the Kentucky side of the river right across from the Great American Ball Park, drinking a beer, smoking a cigar, and chatting with the waitresses when we saw Ken Griffey Jr hit a home run on tv. Then the fireworks started shooting up from the ball park. pretty cool! That was the last time i have had a Helix cigar. I cant find them here in Northern Indiana. CAO is probably my favorite maker right now. Connecticut wrappers, 5″ and a 48-ish gauge. Shock top on draft, and a bon fire. Good times!

510 Michael November 4, 2009 at 10:29 pm

I was studying abroad in Europe last semester and decided to take a week to visit Venice. While I was there, I decided to purchase a Cuban cigar, something I had only ever imagined of doing in the United States. With two other friends in tow, I sat down along Venice’s Grand Canal with nothing but the stars overhead and smoked my first Cuban cigar.

I will never forget that night.

511 Chris November 4, 2009 at 10:37 pm

I would have to say that my favorite regular smoke is La Vieja Habana by Drew Estate, but in Canada I prefer Romeo y Julieta Churchill Cubans!

512 Blake Zollar November 4, 2009 at 10:44 pm

Rocky Patel has a great line of moderately priced cigars. I enjoy the Edge (Sumatra if you can find it) and the Vintage ’90s.

513 Josh November 4, 2009 at 10:54 pm

Once the fall season comes around, my favorite way to enjoy a cigar is with a complementary bourbon and a fire in the back yard. But don’t just grab any stick and any drink. Talk to your local cigar dealer and match up the two. Some cigars can’t handle a strong in-your-face bourbon like Booker’s, others (I’m thinking Padron 1926 Anniversary)…well that just a great night!!!

514 Padraig November 4, 2009 at 11:01 pm

I love La Gloria Cubana cigars. Dominican Romeos are great too.

515 Sean November 4, 2009 at 11:36 pm

My favorite Cigar experience came while in undergrad at The University of Arizona (Bear Down Wildcats!) at the start of Christmas break. Being an RA, we had to stay after all the residents left for break and that meant party time in the dorms! Being the oldest dorm on campus (anybody know which I speak of?) there were only 6 of us RA’s but we invited the other small dorms over to enjoy. Needless to say, debauchery ensued and great time were had by all. The evening ended with late night pizza and cigars with my fellow RAs on the roof of the dorm. To say I was (and still am) rather ignorant as far as good cigars go, we did frequent the local humidor (Anthony’s Cigar Emporium) and took the advice of the fine gents there.

Recently, I have wanted to get back into the habit of sharing a good smoke and drink with good friends, but do not know where to start. This would be the perfect way to start!

516 Mark Perilman November 5, 2009 at 12:23 am

My cigar spreadsheet that I keep a bit too meticulously will tell you that my favorite cigar when considering the taste/value relationship is an Arturo Fuente Hemingway (Churchill). I smoke too often to spend more than $10/stick on any kind of regular basis. How do I partake in said cigars? Well let me count the ways! 1. Golf … imperative. The cigar clip that clips to the steering wheel or cart is a must … considering they are under 10 bucks a pop I weep for my friends who must prop their stogie up on a tee or worse yet lay it on the ground to taint the taste with whatever the groundskeeper decided to spray that morning. 2. Though not considered proper cigar etiquette (primarily since you aren’t getting the intended message from the cigar), I will smoke the same cigar for 2-3 days in my car on the way home from work. Nothing better to lower the stress level on the highways. Get home … use the same cigar clip to clip it to the visor. Light up at 5 pm the next day! and finally … 3. I have three kids and I try to keep the smoke away from them but … stogies make me a better dad (I know it sounds like b.s. but it’s true) … I will play outside for hours more if I have a cigar on hand. I walked them for many blocks more when they were babies than I would have sans cigar. I have some proud moments but none finer than when I wheel my baby’s stroller down the street puffing away and watching the moms look out their front doors in disbelief … everyone should try this once!

517 Brian November 5, 2009 at 12:26 am

For you guys at that awkward age between 18 and 21 (you can smoke but can’t drink yet) I found that a cigar pairs very well with a good root beer. Of course, after I turned 21 I moved on, but “beer” and smokes was a regular occurrence to celebrate the end of an academic semester for my friends and I.

518 Jared DuBach November 5, 2009 at 12:56 am

Good info on the Cuban. Will have to try that if/when I get up to Canada. My dad smoked one once in Ireland, but he hardly smoked cigars so I couldn’t put much stock in his opinion.

As far as domestic cigars, I’ve mostly had to stick to cheaper machine manufactured brands such as Grenadiers (cuban seed tobacco) and my old standby — Backwoods. Whenever I smoke it I’m reminded of Clint Eastwood in the spaghetti westerns. When my dad ran a tavern, Dutchmasters Panatelas were the most popular, followed by White Owls. Of course, in college guys like Black and Milds. Some would use them for alternative purposes….

519 Tony Literski November 5, 2009 at 1:13 am

Even though it is a flavored cigar, I recommend that everyone try The Drew Estates’ ACID line of cigars. they are infused with many other oils and herbs. more of a piney, cedar,floral taste. This is best accompanied with a good single-malt scotch( or cognac) in my opinion. The whole experience is meant to relax, reflect, and savor on the past, present, and future. my advice would be know your “season”;there is a time or “season” for everything. (you can smoke cigars year round), just wisely choose when and where..

520 Raghav Srivastava November 5, 2009 at 4:47 am

Up til now, I have not had the pleasure of smoking cigars on an all-too-regular basis. I gotta say, though, that i definitely prefer cigars that either bold or spicy in flavor, most likely because I have no sense of smell to speak of :-p

521 Michael November 5, 2009 at 7:05 am

We had just returned from Iraq, and – in attempting to return to my old routines -wanted to pick up a few good smokes. I usually favored a maduro and wanted to try a little variety when I picked up a cigar named Diana Silvius.. it was exceptionally well made! So that night, after most of the guys in my unit had a chance to decompress, we got together around the bonfire, and I passed out my cigars as gifts for my brothers. It was funny to watch men try to choke down a cough, but it was a great time and fantastic memories!

522 Joel November 5, 2009 at 8:10 am

I’m personally a fan of CAO cigars.

523 Brandon November 5, 2009 at 8:48 am

I’m a big fan of the Padron Churchill Maduro, but lately to allow me to smoke more without breaking the bank I’ve found myself buying a cigar by Pepin Garcia called Benchmade. It’s much cheaper but still a great smoke if you like a full bodied spicy cigar.

524 Philip H November 5, 2009 at 9:04 am

I overwhelmingly agree that cigars are best enjoyed with a nice beer while sitting on the deck and conversing with friends. Try a Macanudo Hyde Park Natural paired with a Shiner Bock or a Baccarat Rothschild (slightly sweet tasting wrapper) with a Shiner Blonde.

525 Mike G November 5, 2009 at 9:10 am

I graduated from Black and Mild and Swisher Sweets with my first Macanudo. I’m still not terribly experienced with cigars, but seem to like all I’ve tried from the MAcnudo line.

526 John B November 5, 2009 at 9:32 am

My father inadvertently turned me on to cigars. When I was young I’d see his crinkly package of backwoods in the cup holder of the car and although he made a point of rarely smoking in front of me, I admired what he was and the cigars were part of that. Today I smoke Padron, almost exclusively. I only smoke once a month on average, so when I do, I light up an anniversario 1964 or 1926. I haven’t tried the 80 year yet. I doubt I’d be able to tell the difference… and I’d rather have two 1964′s for the same price.

527 J November 5, 2009 at 10:07 am

I used to only smoke two different cigars by Drew Estates called the Java (like smoking a coffee:) and the acid line. However, my tastes have started to mature and I have branched out to the regular cigars. My current favorite is the Rocky Patel 1990 vintage. I did however, try a cuban that friend had “Imported” and it was quite excellent.

It’s nice to have kind of a tradition with friends where we can just sit smoke and chat once a week or so. With all of my friends getting busier with careers and school, sitting down with a nice cigar is a pleasant distraction.

528 Ryan November 5, 2009 at 11:30 am

I’m a big fan of Arturo Fuente cigars. They’re a little lighter than what my friends usually smoke, but I prefer them. The best times I’ve had with my friends included a cigar a bottle of scotch, and a wonderful summer evening. Because of families and careers we can only do this a few times a year, but we all look forward to it.

I wonder if anyone here would be able to help me. I love one cigar, but I have been having a hard time finding it in my local area (Hudson Valley, NY). It’s called El Hemingway. I got it while on vacation in Key West, FL, and I have been looking to find it sold in a nearby store, but cannot.

529 Zac November 5, 2009 at 12:47 pm

I have found the Gurkha line of cigars to be tasty and reasonably priced. However, I have not had luck with their Micro Batch offerings.

530 Tarl November 5, 2009 at 1:36 pm

My favorite cigar smoking experience occured on my honeymoon. My wife and I went on a cruise to St. Martin and St. Thomas, while there we purchased a couple of cuban cigars. While they were very good, I wouldn’t say they are the creme de le creme of the cigar crop, but the circumstances of our smoking were outstanding. Sitting on the deck of our ship, at sunset with a couple of drinks we smoked our cigars and celebrated our new union. It was an amazing memory.

531 Ryan S November 5, 2009 at 1:45 pm

My first cigar was given to me while on a short tour with a jazz band my freshman year of college. It was a very manly experience to be given a cigar by older, well-traveled musicians and let in on discussions I had never been privy to. This was also the night I was introduced to scotch. While I found both scotch and cigars disgusting at the time I have now come to have a passion for both. I can hope only to pass a similar introduction to the round table of men to another young man someday, perhaps a son.

532 Jake Benson November 5, 2009 at 1:52 pm

While I am not a particularly skilled cigar aficionado, I figure what better way to improve my tastes than the cigar of the month club. I am generally stuck smoking the discount models, relying on friends to find me a good smoke. I would be lying if I said I am not incredibly excited about beer. Beer – that’s where I’m a viking.

533 Tom November 5, 2009 at 2:03 pm

Anywhere that society or the wife doesn’t frown at you is a good place to smoke.

534 Andrew November 5, 2009 at 2:23 pm

My favorite cigars are from the Romeo Y Julieta brand. They are relitively cheap, can be found in most all places cigars are sold, and reliable. My buddy and I always smoke them.

535 Andrew November 5, 2009 at 2:46 pm

Though I don’t get to smoke cigars as often as I’d like, I have a great cigar-clipper that makes a nice V-shaped hole in the end (or “head,” I see above). I also have an ashtray with the flag of the Soviet Union on the bottom I love to use to catch my cigar remains. I call it “the ash heap of history.”

536 Brian November 5, 2009 at 3:06 pm

Rocky Patel and CAO are two of my favorites…whatever the size, shape, or style, these two brands always seem to deliver. For the newer smoker, I recommend AVO, I started with those, because they were much milder than most others. There is nothing more “Manly” than a stogie with your best buds and your drink of choice…port, scotch, etc. My mouth is watering just thinking about it!


537 Nathaniel November 5, 2009 at 3:57 pm

Spending a year in Japan really made me appreciate good tobacco, especially cigars. I took 4 Padron 1964 Exclusivo’s to tie me over. When those ran out, I was stuck with a limited range of bad cigars… those were sad times. Coming back to the States and having a good range of Nicaragaun tobacco has been great!

538 Sal Ortega November 5, 2009 at 4:07 pm

The first cigar I ever smoked was a Dunhill EMS. It was remarkably smooth and creamy. I had just turned 21 and a co-worker gave one to me. From that moment on, I was hooked.

539 Jim Jorgensen November 5, 2009 at 4:23 pm

Never smoked a cigar but love a fine beer.

540 Charlie November 5, 2009 at 4:39 pm

Don Lucas cigards, by far the best I’ve smoked in years. Smaller, flavorful and savory.

541 Patrick November 5, 2009 at 4:55 pm

I’m a fan of the Rocky Patel Edge (toro corojo to be exact), and I seem to be in good company judging by the other comments. I find them well made, spicy/flavorful and generally a great deal for the price point. The warning on the box that they are for “serious smokers” or something like that seems a bit out of place. I’ve yet to keel over due to their strength. Still they are a full-bodied smoke.

542 Troy Fisher November 5, 2009 at 5:13 pm

While reading the article I was struck by the sentance “Cuban cigars are indeed better”. Then later “The cigar-smoking experience is very personal. Everyone has different tastes”.
One of my favorite cigars is Cuban (Partagas, Series D #4), but that doesn’t mean that they all are better (better being VERY subjective to personal preference).
I’ve smoked too many to count & have found many that will give a Cuban cigar good competition. A good example is Romeo & Julieta Reserve Real (drooling just thinking about it).
Don’t believe the hype; trust your experience (try at least 4-5 of a brand/size; size DOES matter) balanced with the experience of others.

543 Matthew November 5, 2009 at 5:55 pm

I’ve never smoked a cigar but I love how they smell.

544 Richard November 5, 2009 at 5:57 pm

My favorite brand of cigar is Partagas. Cuban or not, I have always found them to be the most reliable no matter what kind I get.

My favorite cigar tip is to those that are trying to cut their cigars for the first time. As long as you don’t have a torpedo, you can get a perfect cut every time by laying the cutter flat on a table/counter, putting the cigar through the hole until it rests on the table. Close the cutter, and you have about as perfect of a cut as you can ask for. The best part is, even when you slip and have an Oops! moment, you can almost always recover with a second cut. The table just acts as a built-in guide.

545 DMart November 5, 2009 at 6:00 pm

I’m partial to anything CAO, particularly the MX2 which is dark and spicy. I also enjoy Drew Estate, including the nontraditional Acid sub-brand. Great for beginners as they are generally light and flavorful. The flat Waffes are particularly interesting, and a great conversation piece.

546 Jim November 5, 2009 at 6:00 pm

I have many memories of my Grandfather, who enjoyed cigars. I remember the smell of the cigar…one of my favorite. I have no idea which brand he smoked or even how often. I will tell you, I don’t remember him without one. He has been gone many years so I will have no way to really know. Now that I am 41, I remember my Grandfather and his cigars, and I have considered having my first. I don’t really know any more about cigars than what I have read on this posting, and trust the many opinions here as to it’s satisfying enjoyment. I look forward to finding one that reminds me of the aroma of my Grandfather. This would be a great way to help find what I am looking for. Who knows, maybe my children, or even grandchildren, will have some of the same fond memories of me than I do of my Grandfather.

547 Norm November 5, 2009 at 6:05 pm

My Go-To cigar is the Romeo and Julietta Reserva Real Robusto. I make time for one every Monday evening.

548 Pete November 5, 2009 at 6:12 pm

The smell of cigars makes me think of my dad. He used to smoke them when he walked his ranch. He used to smoke Swisher Sweets. By the time I got older and learned how much better cigars there were and would have gladly bought him some, he was no longer around…

One of my favorites is Don Diego Lonsdales. It is a very smooth smoke.

549 Eric Williamson November 5, 2009 at 6:17 pm

No matter where you go, there is nothing that beats a Rocky Patel Vintage 1990.

550 El Buzadero November 5, 2009 at 6:46 pm

The best cigar I ever had was in Nassau, Bahamas in 1999. We were doing a job there for about 3 weeks and got shut down for weather for two days. Came across the island to Nassau and got rooms. It was in between cruise ships and the town was almost deserted of tourists. I walked up the stairs above some street level shops to the Casa del Habano, the Cuban government’s state owned cigar store. For about an hour and a half I was the only customer in the store. The woman who ran the place was a smaoking hot Cubana who spoke perfect English and claimed to have a degree in tobacco agriculture from the University of North Carolina. She gave me a very comprehensive lesson in Cuban cigars,counterfeits, counterfeit labels and boxes, cigar storage, wrappers and much more. I ended up splurging on my Amex Card for a 1968 Montecristo and some 20 year old dark Cuban Rum. I sat with her and talked out on the balcony over the street and watched the day fade into evening out over Nassau Harbor. Some of the best money I ever spent.

551 JadoJodo November 5, 2009 at 7:03 pm

My first cigar was a Camacho cigar that I received for free. I enjoyed it, though I accidentally inhaled the first time. I felt dumb.

552 rob November 5, 2009 at 7:09 pm

hey guys! Thanks for doing the article that I suggested!

553 Mike Hodgman November 5, 2009 at 7:41 pm

Favorite experience of cigar smoking was during college visiting Detroit and smoking at a Greek restaurant in Greek Town “The Pegasus”. Just great.

554 Mike Cisneros November 5, 2009 at 7:46 pm

Excalibur #4 are my favorites. And yes I have a source for Cubans

555 Eric J November 5, 2009 at 8:34 pm

My first cigar experience came from a college friend who happened into a chance excursion down to Cuba. Upon his return he regaled us with tales of summertime in Havana while we lounged on our porch enjoying our smuggled Cubans and cayparenias.

556 NAWEST November 5, 2009 at 8:51 pm

My first cigar was bought at a gas station. It just tasted like burnt paper. As the article said, money isn’t everything, but I don’t think you can get a good cigar for 50 cents either!

557 jon November 5, 2009 at 10:09 pm

Punch Rothschilds; Padron 3000s.

Best cutter? My experience has been good with a rolled blade cutter (sometimes found in the 45 magnum cigar cutters). Simple twist and you’re through without crushing any of the outer wrapper or wondering when to stop. Even draw, every time.

Went from smoking 2/day to smoking 1/year on my birthday… :o(
Guess I’ll go light up before today’s over!

A Fuente curlyhead this year… yum.

558 Casey November 5, 2009 at 10:16 pm

My favorite cigar I’ve found through a long tobacco filled journey is the H. Upman Vintage Cameroon. My friend had suggested it to me when we were having a cigar social at my house, and I have to say that I quickly fell in love.

559 Tim November 5, 2009 at 10:17 pm

One of my favorite cigars was hand-rolled by master artisan Dagoberto in the Ybor City Museum in Ybor City, Florida, the former cigar capital of the United States. There’s nothing like watching a guy roll a cigar and then hand you one that’s at its peak, ready to smoke. Heaven.

560 Jason November 5, 2009 at 10:42 pm


561 Brian November 5, 2009 at 11:01 pm

When I turned 18, merely 3 years ago, my best friend’s stepfather, a descendant of the late Al Capone (no exaggeration), showed me his cigar collection. Before that day, I’d never tried a cigar, or even a cigarette, not even a puff. I was treated to a sight of a beautifully kept den, complete with overstuffed leather chairs, highly lacquered tables, and a hutch cabinet with three identical humidors. The humidors were each fairly small, about the size of an average shoe box. In two of the ornate boxes were fine Dominican, Honduran, and Bahamian cigars. In the middle humidor however, were his collection of various brands and styles of authentic Cuban puros.

Opening that box yielded the most delectable odor of Spanish cedar, and fine tobacco wafting through the air. Selecting 3 cigars (one each for me, my friend, and himself) my host sat us down and over the next twenty minutes explained to me the finer points of cigar smoking and the hobby in general. I properly clipped the head of my cigar, lit the foot, expelled the first puff, then inhaled a long steady draw and kept the intense cedar flavored smoke in my mouth. By the time we had all lit out cigars and were well on our way to filling a solid glass ashtray, my host had served us a generous portion of brandy out of a decanter. The combination of flavors, smells, textures, and overall overwhelming of my senses was a very important and significant turning point for me. It was then at merely 18 that I knew that this sort of pleasure need not be reserved for those “old gray haired fellows”. A good drink, fine cigar, and better friends, is not dated, its timeless.

Now, while I am still a young man by most standards (21), I have “converted” dozens of friends and colleagues to the hobby and have enjoyed many long nights and intense debate, witty anecdotes,and thrilling stories over billowing cigar smoke.

That first cigar was a Cuban Monte Cristo #4, of which I still have the band tucked away in my humidor.

562 James Grant November 5, 2009 at 11:14 pm

What a great giveaway. My favorite right now is a Rocky Patel.

563 Aaron November 5, 2009 at 11:27 pm

My favorite cigar, or should I say my most memorable cigar session, was smoking a wonderful Cohiba Red Dot over a bottle of Glenfiddich Twelve Year with a good old friend who had just returned home from being overseas in the Marine Corp for more than two years. Never a better combination of cigar, scotch, and company.

564 John November 6, 2009 at 4:23 am

having a cigar with a friend while fly-fishing, after his first child was born is a memory I’ll always cherish!

565 Jerrick Irby November 6, 2009 at 8:43 am

Great article!

I enjoy 5-6 cigars a year – smoking a cigar is a rare pleasure for me. I enjoy CAO, Romeo y Julieta, and Rocky Patel lines.

I’ve had many good cigar moments. My wife smoked her first cigar with me. Lots of cigars on the back porch with good friends. But my favorite cigar moment had to be as a senior in high school. Three of my best buds and I went backpacking for a week. Our “essential” gear included several stogies each! I can vividly remember sitting around a campfire on a brisk, clear spring night smoking our sticks, talking about the life we had lived, the life we hoped for in the future, and creating more memories as we went. It was a rare and memorable bonding time. To this day when I smoke a cigar on my back porch, if I close my eyes, clear my mind and listen, I can feel the warmth of the campfire, smell the smoke in the air, and hear our youthful voices of yesteryear.

Thanks for bringing me back to those memories!

566 Paul November 6, 2009 at 9:24 am

I like a strong, full bodied cigar like Onyx Reserve. Trends in ring guages don’t affect me: I like a robusto.

567 Mark November 6, 2009 at 10:44 am

The first Cuban I smoked was in Spain, on a trip through the country. I don’t know if it was the cigar itself, or the great Brandy that accompanied it, but it was fantastic. Oh, I know…maybe it was the sweetest because I didn’t have to pay for either one!

568 Christopher Hughes November 6, 2009 at 10:58 am

I have enjoyed the occasional cigar for years now. Despite trying an actual Cohiba Esplendido on a fishing trip in Canada years ago (which I found to pleasant yet overpriced), I maintain that there are numerous Dominican cigars that are fantastic and
quite reasonably priced. The best pieces of advice that I can offer any cigar smoker, both new and experienced are : 1) Do your research and talk to your tobacconist as much as possible before buying, and 2) ALWAYS put the unlit end in your mouth !!!!

569 Trent November 6, 2009 at 12:30 pm

My favorite brand is Romeo y Julieta. It has a strong tabacco flavor without being too overpowering. I remember my friends and I smoking this cigar off a dock one night in Montego Bay, Jamaica. With the smell of the ocean and cigar smoke in the air it felt very manly.

570 Mathew November 6, 2009 at 1:23 pm

My favorite cigar experience was this past June two nights before my wedding. Three of my groomsmen, brothers with whom I had all shared more memorable moments over stogies than can be counted here, were all finally brought together at the same time to enjoy each other’s company and love for fine tobacco and Irish Draught.
My suggestion actually comes from one of those guys, Curt, who as we discovered over the past year that it doesn’t depend on how fine a quality cigar you purchase sometimes there are flaws in the rolling that without a cigar “poker” can ruin what otherwise would be a great smoke. A one-time investment of $20 on a cigar poker can save countless sticks that would otherwise be wasted money.
Favorite Brands include (amongst others): Fuente, La Gloria Cubana, Partagas and Olivia

571 Lucas E Szymanowski November 6, 2009 at 2:05 pm

Another idea for getting your hands on cubans is to travel to mexico. They easy to get there. While I have family in Costa Rica, I’ve always planned a short hop to Cuba in person, since CR doesnt have an embargo in Cuba.

572 Justin November 6, 2009 at 2:07 pm

My favorite cigar: Oliva Serie G. And, even though nobody asked for a favorite beer, Edmund Fitzgerald Porter, from Great Lakes Brewing Company, is perhaps the best dark beer I’ve ever tasted. Check it out.

573 Kirk November 6, 2009 at 3:13 pm

In 1992, a girl I loved broke up with up me because she felt I wasn’t ready to commit at 21 to a deep relationship. She told me then that if I’d shown some sign, given her some indication that I was in for the long haul, even a cigar band would have sufficed, that she would have stayed. Eighteen years on, both married and divorced, we connected again, and at our first in person meeting, in my pocket sat a fine Romeo and Julieta Corona, that I pulled from my pocket, knelt on one knee, removed the gaudy red and gold band, and slipped it on her finger saying “Do you have plans for the next 40 years”. She replied “No”. To which I responded, “You do now”. We’ve been married for 6 months towards that 40 years now. On my way home from that first encounter, I smoked that cigar, long and slow and it was the most memorable smoke I’ve ever had. Never underestimate a good cigar.

574 Matt Bunn November 6, 2009 at 3:49 pm

Nica Libre has been a recent favorite. Smooth and won’t break the bank

575 Adam Brewer November 6, 2009 at 4:03 pm

cant go wrong with a montecristo #3 and a Sam Adams Octoberfest… perfect for tailgating saturdays in the SEC

576 Nathan November 6, 2009 at 4:15 pm

Cohiba Esplendidos on the honeymoon on the beach in Cozumel. No cigar will ever compare!

577 Nate November 6, 2009 at 4:45 pm

I started with Swisher Sweets when I was 18 and quickly moved from there to flavored cigarillos. Within a year I’d had my first real cigar, the Excalibur 1066 Dark Knight, which I still consider today to be one of my favorites. I also enjoy Partagas, Macanudo, and an occasional Ghurka. Theres nothing like a good cigar, good friends, good drink and a good game of poker.

578 Mr. C November 6, 2009 at 5:43 pm

Smoking a cigar with my buddy Keith on his deck. Our wives work together, and when we finally met and and hung out, an evening of good beer and conversation led out to the deck for a smoke and the beginning of a beautiful friendship.

579 G November 6, 2009 at 8:33 pm

Cigars make great client gifts! (Love them myself.) They’re also wonderful on camping trips. Besides a great experience, cigars keep the mosquitoes at bay wonderfully well.

580 MattW November 6, 2009 at 10:07 pm

I do need to expand my cigar experiences – but I do love a Macanudo.

581 Tyler Hayes November 7, 2009 at 12:58 am

Can’t say I really knoe cigar brands well, but my fave experience was buying a legit hand rolled in mexico. Unbelievable flavor.

582 Ben DeLost November 7, 2009 at 3:05 am

I bought a humidor a few years ago and invested in some decent cigars. Great investment and I have been able to enjoy a great cigar whenever I want. Just have to make sure to maintain it or it can be hard to get it back to normal.

583 Cameron A November 7, 2009 at 3:23 am

I don’t know too much about cigars, but I do remember the best one I’d ever had was when I watched the women rolling the tobacco and then buying one fresh off the line. Smoked it that evening, watching the bay. One of the most amazing nights.

584 Stillehavet November 7, 2009 at 8:59 am

Happily partook in the celebration of a good friend’s first son birth by sharing “It’s a boy” Cohiba’s. Never looked back to see if there was another brand to consider. A little later in life a mentor helped to find the nuances of a Cohiba and a never ending bucket of Glenrothes. Ahhhh…

585 Bill Hertzing November 7, 2009 at 9:31 am

My personal fav is the Partagas Black. Smooth, even smoke. A tad robust but not overpowering.

586 Bob Chesson November 7, 2009 at 10:00 am

Being a lover of full flavored food and drink (red wine, stouts, etc.) I have found, no big surprise, that my cigar tastes to run more to full bodied smokes. I am partial to maduro rubustos private label my local shop stocks (Nicaraguan). My best tip – don’t light your cigar with matches but use a butane (not lighter fluid) lighter. Matches (and non-butane lighters) leave an off taste to your smoke due to the chemicals used to promote longer burning (matches), and in the case of lighters, a ‘lighter fluid” taste. Both can ruin a good smoke.

587 Vladislav November 7, 2009 at 10:11 am

At our monthly 7 card stud table, Henry Clays and Bahias are the favorites.

588 Paul Hunter November 7, 2009 at 10:11 am

I have never yet smoked a Cigar, but the best memory I have associated with Cigars was when the men of my college dormitory organized a cigar party one night, and invited professors to come and join in reading and discussing poetry while smoking cigars. I partook of conversation but not of cigars. It was a bit pretentious, but it felt extremely intellectual (even a bit bohemian) to sit in the courtyard of out dormitory enjoying the smell of good cigar smoke and the sound of poetry and conversation. Fortunately, pretentious intellectualism is forgivable in college.

589 Joe November 7, 2009 at 11:41 am

My first cigar was probably a Phillie unfortunately. However, over time I have progressed to enjoy some of the finer points in life. Though I must say I am a big fan of the playboy roll from JR Cigars. And my true favorites are Davidoff’s. They just have a superb flavor. I hope that I can win this contest and for luck I will go light a nice Trinidad Cigarillo now. Cheers

590 Andy November 7, 2009 at 1:13 pm

My favorite experience with a cigar was at my cousin’s bachelor party. We were in a casino, and I picked out a couple Dominican ones to smoke. We sat in a bar, had a few drinks and smoked for about an hour. It was a great time.

591 Chris November 7, 2009 at 2:34 pm

Definitely CAO Gold

592 Sam November 7, 2009 at 4:18 pm

Relaxing with a fine cigar and a drink after a BBQ on a warm California night with best buds around … hard to beat.

593 Marlin J Harris IV November 7, 2009 at 5:08 pm

The most enlightening and enjoyable conversations I have ever had have been accompanied by the beautiful aroma of a cigar. My first experience being with a hearty flavored Monte Cristo.

594 Rafael Lopez November 7, 2009 at 5:56 pm

My first cigar was a Romeo y Julieta. I had just turned 18 and everyone was buying cigarettes, so I decided to go big. No worries, I didn’t smoke like a chump and turn green, but I definitely didn’t enjoy it to the fullest extent.

595 Eric November 7, 2009 at 8:13 pm

The most embarrassing cigar experience I ever had was in Vegas. I was playing roulette and the server came by so I purchased a Romeo y Julieta. About 10 minutes later there I was smoking away when I needed both hands to play. Like a total amateur, I bit the cigar in my mouth to free up both hands, and promptly started inhaling…the coughing attack was so intense, I spill my drink everywhere!

596 Jimmyj November 7, 2009 at 10:30 pm

My best cigar was a Monte Cristo bought at a small cigar shop in Nuremberg, Germany. Very smooth tasting! Thank you for this giveaway.

597 Donald Sturman November 8, 2009 at 12:49 am

Favorite(s):This is such a tough choice because there are so many great cigars in the world, but if I had to choose one it probably is the Romeo and Julieta for mildness, overall consistency of flavor, and unparalleled quality. Having said that, I have grown to really enjoy and appreciate dark Cameroon wrapped cigars for there mildness, smooth draw, and even consistent burn. Brands such as Oliva, Gurhka, and Aspira also make wonderful cigars.

Tip: If you decide to smoke cigars then you need to invest in good tools: a great guillotine cutter and a strong flame throwing lighter. These two tools will add so much enjoyment to your experiences.

Experience: The best experiences I have had are hanging out at my local cigar shop in the company of other good men watching football, hanging out with friends, and enjoying an adult beverage. There is something super special for me about smoking Churchill cigars, its a bonding experience and it makes me feel good.


598 Steve-O November 8, 2009 at 10:16 am

I love CAO cigars. Pretty much every product in their line is great, but my favorite is the Criollo

599 David Hurtado November 8, 2009 at 2:11 pm

It would be nice if we could get that embargo to go bye-bye so that I can smoke myself those amazing Cuban cigars!

Dying to win one of these AoM giveaways!!!! Come on!

600 William November 8, 2009 at 4:21 pm

Thanks much for the fine article. I hardly EVER smoke cigars anymore except when camping. Something about sitting outdoors in front of a roaring fire.

My first cigar was a Swisher Sweet! Ye Gods!

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