How to Smoke a Cigar: A Calm Guide for Your First One

My first cigar was a disaster. I was 31, standing on a hotel balcony in Miami with a client I'll call Mr. Reyes. I cut off half the head, torched the foot with a jet lighter, and puffed like I was trying to start a lawnmower. It went out twice. Mr. Reyes relit it for me, laughed, and said, "Don't rush it. You'll insult us both."

That's still the best advice I know. Everything below is just the details.

Step 1: Pick a cigar that fits the moment

For a first cigar, go mild to medium and go modest in size. A robusto (around 5 inches long with a 50 ring gauge) or a corona gives you 30 to 60 minutes, which is plenty. A Connecticut shade wrapper, the pale golden-tan leaf, usually reads smooth and creamy. It's a good place to start, and plenty of veterans smoke them on purpose. If you want names, our list of the best cigars for beginners has eight easy starting points, from the Macanudo Cafe to the Arturo Fuente Hemingway Short Story, a small cigar with a story worth reading.

Buy from a shop with a proper walk-in humidor, and ask the person behind the counter what they'd hand a friend. Good tobacconists love that question.

Pro tip: Squeeze gently. A well-kept cigar should feel firm with a little give, like a ripe piece of fruit, not crunchy and not spongy.

Step 2: Cut just the cap

At the head of the cigar (the end you'll put in your mouth) there's a small round piece of leaf called the cap. It holds the wrapper together. Your job is to remove just enough of it to open the draw.

With a guillotine cutter, which is the most common kind, line the blade up so you only take off a sliver, usually about 1/16 to 1/8 of an inch, staying above the "shoulder" where the head starts to curve. Then cut in one quick, confident motion. Slow cuts tear.

Cut too deep and the wrapper can start to unravel. Cut too shallow and the draw will feel tight. You can always take a little more. You can't put it back.

Other options work too. A punch makes a small round hole in the cap and is great for travel. A V-cutter makes a wedge that concentrates the smoke. Pick one and learn it.

Step 3: Toast, then light

Use a butane lighter, a torch, or long wooden matches. Skip candles and fluid lighters, which can leave off flavors in the tobacco. If you use a match, let the sulfur burn off first.

1. Toast the foot. Hold the open end at an angle just above the tip of the flame, not in it. Rotate slowly until the whole face of the foot is glowing at the edges. 2. Light it. Put the cigar in your mouth and take slow, gentle draws while rotating it near the flame. You want the flame to be pulled toward the foot, not jammed into it. 3. Check the ember. Gently blow on the foot. It should glow evenly all the way around. If one side is lagging, touch just that side with the flame.

That's it. A proper light sets the tone for everything that follows.

Step 4: Draw, don't inhale

Cigar smoke is for your mouth, not your lungs. Draw gently, hold the smoke for a moment to taste it, then let it go. Think sipping, not gulping.

Pacing matters more than anything. Puffing too fast makes a cigar burn hot and bitter. Puffing too slow can let it go out. A draw every minute or so is a comfortable rhythm for most people. I time mine with records. A robusto is about two sides of an album if you're doing it right.

Some people like to retrohale, letting a little smoke out through the nose to pick up more aroma. It's optional. Try it once you're comfortable, with a small amount of smoke.

Step 5: Let the ash be

A firm, even ash is a sign of a well-made cigar and a patient smoker. You don't need to tap it off constantly. Let it build, and when it's about an inch long, or when it's ready to fall, roll the cigar gently against the edge of the ashtray. It'll come off on its own.

Hard tapping is a lounge pet peeve of mine. The ash didn't do anything to you.

Step 6: If it goes out, relight calmly

Cigars go out. It happens to everyone, especially early on. Tap off the loose ash, blow gently through the cigar to clear any stale smoke, then toast and relight the foot the same way you did at the start. No drama.

If it keeps going out, it's often a humidity issue. A cigar that was stored too damp can be hard to keep lit. That's a storage question, not a skill question, and our guide to storing cigars without a humidor walks through the fix.

Step 7: Know when you're done

You don't have to smoke a cigar to the very end. Most people stop somewhere around the last third, when it starts to get hot or harsh. That's the cigar telling you the night is over.

Don't stub it out like a cigarette. Just set it in the ashtray and let it go out on its own. It will, quietly, within a few minutes.

A few manners that make it better

• Ask before you light up around other people.
• Keep the cologne light if you're heading to a lounge.
• Never smoke around kids.
• A pairing is an invitation, not a requirement. Coffee counts. So does water.

Write down one thing

Here's the part nobody tells you. The first few cigars all blur together unless you write something down. For about five years my tasting notes were one word long: "Good." That's not a note. That's a shrug.

Try this instead: the cigar, where you were, what you were drinking, and one flavor you noticed, even if it's just "cedar" or "coffee" or "kind of peppery at the end." In a month, you'll know what you actually like.

When you're ready, log your first smoke in LongestAsh and let the notes do the remembering. Take your time.