Become a Cigar Smoker in 5 Easy Steps – How to Buy Cigars


A guy in my office recently asked how he could become a cigar smoker. After telling him that smoking cigars is a hobby, not an addiction, and blah blah blah, I realized that new cigar smokers and cigar smoker wannabes could use a little guidance. Over the course of five blog posts, I will share my advice on how to become a cigar smoker in 5 easy steps. I thought I could pull this off in a single post, but damn, there is a lot to learn new cigar smoker! So let’s get to it with Step One – How to Buy Cigars.

Step 1: Buy Some Cigars

The first thing to do is buy some cigars. Duh! Easy, right? Not so easy. If you are married or have a significant other, the first thing to do is to tell your mate that you plan to smoke cigars. This can be tricky. Perhaps your wife is 100% anti smoking and you’ll have to convince her that smoking cigars is safe. Perhaps your significant other will question the cost of cigars and you’ll have to agree on a budget. Or maybe, just maybe, you’ll get lucky like I did. When I decided to start smoking cigars, I didn’t tell my spouse. I just bought a few sticks and she came home from work as I was smoking a cigar on the front porch. She sat by me and said, “That smells like Grandpa.” Lucky for me, her Grandpa chain smoked cigars when she was young and she has a great memory that was triggered by the cigar smoke. What did I say? “C’mon over here and sit on Grandpa’s lap!”

Flavored Cigars

To prep for this article, I thumbed through the latest Cigars International catalog and I remember now how confusing it was to pick out a decent cigar when I first started smoking. How do you know what a “good” cigar or a “bad” cigar is? Good versus bad is in the eye palate of the beholder herfer. You decide what you like and smoke what you like. Don’t let anyone tell you a cigar is bad. However, as a new cigar smoker, you need a guidepost on either end of the spectrum so you don’t royally screw this up.

To start with, unless the cigar is made by Drew Estate or CAO, avoid flavored cigars. Yes, I know that some of the readers don’t agree even with the Drew Estate or CAO statement but bear with me. Actually, I wouldn’t be caught dead with any flavored cigars but I thought I would give Drew Estate and CAO a bit of deference. Scratch that, I love the Drew Estate Tabak Especial Negra cigar! Avoid cigars like the Brighton’s Best Cherry, Melon, Mango, Blueberry, Peach, or Fruit Punch cigars in the latest Cigars international catalog. I’m sure someone buys them and likes them but the reality is that they are sh#( cigars to a cigar aficionado. Any cigar with fruit in it is not the direction you want to go. Also, avoid any cigar with the word “honey” in it. The waitress at the local diner can use the word when she takes your order but premium cigar smokers don’t generally go for honey-flavored cigars.

House Brands

Now that we have the flavored cigar thing out of the way, the next point is to avoid house brands, off brands, sh(* brands, machine-made brands, and brands that are filled with sh$% and sticks and used condoms. This will take some time for new cigar smokers as heck, you have no idea what a premium cigar is. There is really nothing wrong with some house brands and most online cigar retailers and many brick and mortar retailers sell house brands. But for a newbie, it is too damn hard to figure out if the cigar is a decent premium cigar or a dog rocket. Expert herfers: insert your favorite Thompson Cigar saying here. Oh, here’s mine. “Friends don’t let friends shop at Thompsons!”


Size matters! Cigars are made in different shapes and sizes. As you try different cigars, you’ll figure out what size is your favorite. I recommend starting with a Corona, Robusto, or Toro. Avoid Lonsdale, Perfectos, Gigantes, etc. at this point. The Robusto is the most common cigar size. If you have no idea what these sizes are, don’t worry. Check out a few websites and smoke a few cigars; you’ll soon learn the difference and figure out what you like.

I plan to write an article about the various cigar sizes at a future date.

Well-Known Premium Cigars

Get a few cigar catalogs from your cigar buddies and review a few cigar websites to learn what cigars are commonplace. Read the description of the cigars and learn about what is on the market. Look to the right of this post. There are a few links to cigar stores for you to start with. Here’s a short list of well-known premium cigars:

  • Alec Bradley
  • Arturo Fuente
  • Davidoff
  • Montecristo
  • Oliva
  • Padron
  • Partagas
  • Punch
  • Rocky Patel
  • Romeo y Julieta
Mild, Medium, or Full?

Cigars are generally considered on a scale of mild to medium to full-bodied. I could write a couple of pages about the differences but you don’t really care at this point. You should start with a mild cigar. If you look at a catalog or online retailer, most either describe or have a graphic showing the strength of the cigar. If you are visiting your local brick and mortar and I highly recommend you start there with your first purchases, simply ask the staff at the shop. Hopefully, you’ll get an honest answer and not a deflection to their house brand where they make the most money.


You can buy a cigar for a buck or thousands of dollars. I suggest you skip the $1 sh*& sticks and you probably aren’t ready for that pre-Embargo 1967 Montecristo #1 for $5,000. OK, I made up the last part but you are new at this so you won’t notice. I suggest you spend between $5 and $10 per stick. If that sounds expensive, get another hobby like penny collecting. Pennies are cheap. Except when they aren’t.

Recommended First Cigars

I recommend the following cigars as you begin your journey in your new hobby. Note: Some of these are affiliate links and we make a small percentage on any sale using these links. Running this site requires funding. Buying cigars using these links helps us pay the bills.

    1. Arturo Fuente 8-5-8 Natural
    2. Macanudo Gold Label
    3. Rocky Patel Vintage Connecticut 1999
    4. Montecristo White Label
    5. Romeo y Julieta Vintage

Don’t buy a box of these cigars. I recommend buying 2-5 of each. Make note of your thoughts on each cigar as you smoke it and then buy a few more. Then, start expanding your horizon by purchasing other mild cigars. After a period of time, your palate will likely change to a stronger cigar. I call it “blowing out your taste buds”. Others might call it “refining your palate.” Either way, I highly recommend against buying cigars by the box during your first year in the cigar hobby.


So your assignment for the next week is to research cigars, pick out a few you like, and buy them. While you are there, pick up a cheap cutter for a buck that will work for now and a box of stick matches. Step Two of this series on How to Become a Cigar Smoker in 5 Easy Steps is to learn how to cut a cigar. Step Three is to learn how to light a cigar. The remaining steps are a surprise! And so it begins. One more cigar brother or sister in the club!


Certified Consumer Tobacconist (Yep, I’m a CCT so you should listen to me. Ha!)



c.gar loves all things cigar-related. He typically falls in love with cigars that are discontinued shortly thereafter. His first cigar was a Swisher Sweet with a wood tip. Sadly, these are still in production.

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