There is something special about pairing a good whiskey with the right cigar.  Taking the time to sit back and appreciate a timeless tradition enjoyed by enthusiasts the world over. Like the shelves at a liquor store, a walk-in humidor can be intimidating – differences in size, color, filler, and wrapper come together in endless combinations.  Vague descriptions might not make a lot of sense if you are starting out and don’t help narrow down your selection.

To help shed some light, I talked to my friends at Habana Cowboy, a mobile cigar lounge. They deliver a premium cigar experience inside TX Pilar,  a ’71 Airstream. With the help of their tobacconist here are a few simple guides to get you started.

Where do you start?

Generally speaking, most should start with a mild cigar with a light body, strength, and flavor. Beginning with a more substantial (or more robust) cigar can lead to a negative smoking experience. These are cigars you can work up to.

Where do you find a good cigar?

Your best bet is your local brick and mortar cigar shop. Speak to their tobacconist. They know the cigars they sell and can make an ideal recommendation.  We do not recommend buying your first (or any) cigar at a gas station or convenience store.

How much should you spend?

There is no reason to break the bank when searching for a good quality cigar.  There are tons of great choices that will fall into a variety of price ranges.  Many premium cigar makers pride themselves on providing a great value.

The most important advice for getting the most out of your cigar (and whiskey) experience is simple.  Take time to slow down and enjoy the moment.

Be sure you have at least 45 minutes to 2 hours to smoke.  Cigars are a commitment and shouldn’t be rushed.  If you can slow down, indulge your senses, and engage in good old fashioned conversation.  It will enhance your experience.

Here are the top 3 recommendations for new aspiring aficionados from Habana Cowboy:

  1. Oliva Connecticut Reserve Toro
  2. CAO Gold
  3. Villiger Connecticut Kreme


Don’t let the choices overwhelm you. Visit your local cigar shop, talk to the tobacconist. They will help find a nice cigar in your price range. When you are ready to enjoy it, relax and take your time.  And a nice glass of whiskey to go with it won’t hurt.

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