A good cigar is about the ritual, the time, the pause it creates in your day.
Winston Churchill understood this better than almost anyone. He picked up the habit as a young man in Cuba, where he'd traveled to cover a rebellion, and never looked back. For the rest of his life he smoked eight or nine cigars a day. Romeo y Julieta was his favorite, though he was loyal to no single size. He was so committed to his cigars that during World War II he had a special oxygen mask made that would fit around one, allowing him to smoke on unpressurized high-altitude flights. His wife eventually designed a bib for him to wear in bed so he wouldn't burn holes in his silk pajamas. He reportedly told his nurse in 1943 that he didn't even like cigars and only smoked a quarter of one. Nobody believed him.
Start Mild
Start with Connecticut-shade wrappers. Mild, approachable, forgiving. If you're not sure where to begin, just ask your tobacconist. Tell them it's your first time and what you're looking for. They've had this conversation before.The Right Cut
A clean cut matters. Too much and you'll get loose draw. Too little and you'll struggle. Right at the cap line. There are a few ways to cut: straight cut, V-cut, and punch cut are the most common. Each changes the draw slightly. A straight cut is the most forgiving for beginners.
Toast, Don't Burn
Hold the cigar at about a 45-degree angle and keep the foot a couple of inches above the flame. The goal is to get the foot glowing without the flame actually touching the tobacco. Rotate the cigar slowly so the whole foot catches evenly.
If you're using a butane lighter, hold it vertical. The flame is hotter and cleaner that way. A torch lighter also gives you more control than matches.
Once lit, check the foot. If you see black spots instead of an even orange glow, don't hit it with more heat. Blow gently on the foot until it evens out. Applying more heat to cold spots pushes tars into the tobacco and ruins the flavor.
Let the cigar sit for about a minute after lighting before your first puff. Everything's lit. Take your time.
Slow Down
A cigar isn't rushed. One puff per minute is plenty. Let it rest. This also keeps the cherry at the right temperature. Too many puffs and it overheats, which turns the smoke harsh and bitter. Enjoy the pace it forces on you.
The Point
It's about taste. Taste a cigar the way you would a fine wine. Notice what you're getting, how it changes, what the finish is like. It's also about the company. Sometimes that company is just you and your thoughts, and that's reason enough.