The old shop on Seventh Avenue had a bench by the window where the late-afternoon light came in sideways through the live oaks, and that is where I learned, somewhere around age twelve, what a cigar actually is. My father, who rolled at Cuesta-Rey before he opened a small shop of his own, would set a Lonsdale on that bench, look at it for a minute the way you look at a piece of fruit at the market, and only then reach for the cutter. He taught me that the smoke is the last part. Everything before it matters more.
I ran Calabrese & Sons in Ybor for forty-two years, and I have watched a lot of newcomers sit down with their first decent cigar and rush it like a cup of gas-station coffee. There is no need. A good cigar is a slow hour, sometimes longer. If you are coming to this in your sixties or seventies, you already have the temperament for it. You just need a few habits.
Pick the cigar before you pick the moment
For a man or woman starting out, I would steer you toward a milder wrapper. A Connecticut shade leaf, the kind you will find on an Ashton Classic, a Macanudo Cafe, or an Arturo Fuente Chateau, gives you a smooth, creamy smoke that does not pick a fight with your palate. Save the Maduros and the heavy Habano 2000 wrappers for later, once you know what you like.
Sizes matter more than people admit. A robusto, about five inches by fifty ring gauge, smokes for roughly forty-five minutes to an hour. A Churchill will keep you sitting for two. If you are new, start with a robusto. Finishing the cigar matters; abandoning one halfway through tells you nothing about it.
One note on what to buy. The premium cigar industry has had a long run of legal fights with the FDA, and as of 2026 the federal courts have held that premium handmade cigars are not subject to the agency's Deeming Rule. Practically, that means your local tobacconist is still around, and the cigars on his shelf still come in without graphic warning labels covering the bands. The federal minimum age to buy any tobacco product, by the way, is twenty-one. If a grandchild asks, that is the answer.
The cigar in your hand
Before you cut anything, take the cigar out of its cellophane and look at it. The wrapper should be clean, no cracks, no soft spots, no veiny ridges running like train tracks. Roll it gently between your fingers. You are listening for a small crackle and feeling for a give that is firm but not hard, more like a ripe avocado than a carrot. A cigar that crunches like a dry leaf has been left out too long. A cigar that feels spongy has been kept too wet.
Smell the foot, the open end. A well-kept cigar smells like hay, cedar, sometimes cocoa or coffee. That smell tells you most of what you need to know.
The cut
The head is the closed end, the part that goes in your mouth. You take a small piece off, not the whole cap. There is a tiny ridge where the cap meets the body of the cigar; you want to cut just above that, no more. Cut too deep and the wrapper unravels on you twenty minutes in.
A guillotine cutter, the kind with two parallel blades, is the workhorse. A V-cut works on most ring gauges and gives you a deeper draw without opening the head too wide. A punch, which takes a small round plug out of the center, is what I keep on my key ring. Whichever you use, make it sharp. A dull cutter tears the wrapper and ruins what comes next. And please, do not bite the end off. I have seen too many bridgework casualties in my day.
Lighting up
This is where most beginners go wrong, rushing through with a jet flame like they are welding. Slow down. A wooden match or a soft-flame butane lighter is best. The big triple-jet torches have their place, but they put too much heat on the foot too fast and you scorch the leaf instead of toasting it.
Hold the cigar at a forty-five degree angle, the flame about half an inch below the foot, and rotate. You are toasting, not lighting yet. Once the foot is evenly dark, put the cigar to your lips, draw gently, and rotate again while the flame just kisses the edge. A few easy puffs and you are going.
If it lights unevenly, do not panic. Touch up the low side with the flame; do not over-smoke to try and even it out. That just gives you a hot, harsh first third.
How to actually smoke it
You do not inhale a cigar. I cannot say this strongly enough. The flavor lives on the tongue and the soft palate, not in the lungs. Take a slow draw, let the smoke sit in your mouth for a second or two, then let it out. Some people exhale through the nose at the end, a retrohale, which picks up spice notes you miss otherwise. Try it once you are comfortable.
Puff every minute or so, no more. Cigars do not need to be babysat; in fact a cigar smoked too quickly turns bitter and burns the tongue. If it goes out on you, that is fine. Tap off the dead ash, relight gently, carry on.
Long ash is a sign of well-aged tobacco with good combustion. You do not have to flick. Rest the cigar on the ashtray and let the ash fall when it is ready, usually somewhere around an inch.
What to drink with it
This is personal, but a few honest pairings:
- Water. Underrated. It lets you taste the cigar instead of the drink.
- Coffee. Cuban coffee on my porch, but any good espresso works. Cigars and coffee share earth, leather, cocoa notes.
- Aged rum or bourbon. The caramel and oak meet the tobacco well. Skip anything too peaty; smoky scotch fights the cigar instead of joining it.
- Port or a dry sherry. An old gentleman's pairing, and an honest one.
Storage, simply
A humidor is just a cedar-lined box that holds humidity steady. Get a small one if you keep a handful of cigars on hand; do not buy a credenza-sized one until you know you need it. The old rule was seventy degrees Fahrenheit at seventy percent humidity. These days most of us run a little drier, around sixty-five to sixty-eight percent relative humidity, especially in a warm climate. You get a cleaner burn and a more focused flavor. A small digital hygrometer costs less than a meal out and will tell you the truth about your box.
Keep the humidor out of direct sun and away from heating vents. Once a year, check the seal by closing the lid on a dollar bill and giving a small tug; if it slides out easily, the seal needs attention.
One last thing
A cigar is not a drink you finish, not a meal you order, not a status pin. It is an hour you give yourself on a porch, after dinner, with a friend or a book or your own quiet thoughts. At our age that hour is the point. Cut clean, toast slow, draw easy, and let the smoke roll.
And if your doctor has told you to leave them alone, listen to him. I have buried friends who did not. But a good cigar, on a good evening, taken seriously and not often, is one of the small civilized things this life still allows. Buen humo.