The first time I tried to smoke a cigar, I made three critical mistakes in the first sixty seconds: I bit off the cap like I was opening a beer bottle, torched the foot like I was trying to set off a smoke signal, and took a deep drag that sent me into a coughing fit so violent the guy next to me offered to call 911. He didn't, mercifully, but he did offer me something better: a ten-minute crash course in not looking like a complete tourist.
That was fifteen years ago, and I've since learned that smoking a cigar isn't complicated, but it does have a few non-negotiable rules. Break them, and you'll either ruin a twenty-dollar stick or announce to everyone within eyeshot that you have no idea what you're doing. Follow them, and you'll look like you've been doing this for years, even if it's your first time.
This is everything I wish someone had told me before I walked into that cigar lounge with more confidence than competence.
Choosing Your First Cigar
Before you can smoke a cigar, you need to pick one that won't immediately humble you. Walk into any decent cigar shop, and you'll be staring at a humidor wall with hundreds of options, most of which will be meaningless to you: Nicaraguan puro, maduro wrapper, ligero filler, 92-rated by some magazine you've never heard of.
Here's what actually matters for your first stick:
Start with a robusto or toro. A robusto is typically 5 inches long with a 50 ring gauge (that's the diameter in 64ths of an inch, because cigar people love making things complicated). A toro is slightly longer, around 6 inches with a 52 ring gauge. Both are forgiving sizes that burn for 45 minutes to an hour, giving you enough time to figure out what you're doing without committing to a two-hour marathon.
Avoid Churchill-sized cigars (7+ inches) on your first outing. They're impressive, sure, but they require more attention to keep burning evenly, and by the time you're an hour in, you'll be wondering why you signed up for this.
Ask for something mild to medium-bodied. Tell the person behind the counter it's your first cigar, and you want something that won't knock you on your ass. A Connecticut-wrapped cigar is usually a safe bet. It's creamy, smooth, and won't give you the nicotine buzz that makes you question your life choices. Save the full-bodied Nicaraguan maduros for when you know what you're in for.
Don't cheap out, but don't go crazy. You don't need a $40 Cuban for your first time. A solid cigar in the $8 to $15 range will treat you well. Anything less, and you're risking a poorly constructed stick that burns unevenly or unravels halfway through.
The Anatomy of a Cigar
You don't need a PhD in tobacco to enjoy a cigar, but knowing the basic parts will help you understand what's happening when you light up.
The wrapper is the outermost leaf, and it's responsible for about 60% of the flavor. It's also the most delicate part, which is why you'll see people handling cigars like they're ancient scrolls. A torn wrapper means a ruined smoke.
The binder is the leaf underneath the wrapper, holding everything together. You'll never see it unless something goes very wrong.
The filler is the blend of tobacco leaves in the center. This is where the complexity comes from—different types of tobacco from different parts of the plant, all contributing different flavors and strengths.
The foot is the open end you light. The cap is the closed end you cut. The head is where the cap is. That's it. You now know more than 90% of people walking into a cigar shop for the first time.
How to Cut a Cigar
This is where most people either overthink it or butcher it entirely. A bad cut can ruin the draw, cause the wrapper to unravel, or make you look like you learned how to smoke cigars from a 1990s action movie.
The goal is simple: remove just enough of the cap to create an opening without cutting into the shoulder (the curved part where the cap meets the body). Cut too much, and the wrapper unravels. Cut too little, and you're sucking air through a pinhole.
The straight cut is the most common and the most versatile. Use a guillotine cutter (the kind with two blades that come together like, well, a guillotine). Place the cigar in the opening, line up your cut about 1/16th of an inch from the cap's edge, and make one quick, confident slice. Don't saw back and forth. One clean motion.
If you're using a cheap cutter, stop. A dull blade will crush the cap instead of cutting it, and you'll end up with a mangled mess. A decent guillotine cutter costs $15 and will last you years.
The V-cut (or wedge cut) uses a V-shaped blade to create a notch in the cap. It gives you a more concentrated draw, which some people prefer. I like it for box-pressed cigars (the ones with a square shape) because it opens up more surface area without risking the wrapper.
The punch cut uses a circular blade to remove a small plug from the cap. It's portable, nearly impossible to screw up, and creates a tighter draw. The downside? You can't adjust it. If the draw is too tight, you're stuck.
For your first cigar, I'd go with a straight cut. It's simple, effective, and if you mess it up slightly, you can usually fix it by cutting a bit more.
How to Light a Cigar
Lighting a cigar is not like lighting a cigarette. You're not trying to set it on fire; you're trying to evenly toast the foot so it burns slowly and consistently. Rush this, and you'll have a bitter, uneven burn that no amount of relighting will fix.
What to use: A butane torch lighter is the gold standard. It burns clean (no fuel flavor), gets hot fast, and works in wind. Soft flame lighters (like a Zippo) work, but they can add a gasoline taste if you're not careful. Matches are fine if you let the sulfur burn off first. Cedar spills (thin strips of Spanish cedar) are the fancy option you'll see in high-end lounges, and they're legitimately great if you have them handy.
Avoid candles, regular lighters that smell like lighter fluid, and for the love of everything, don't use the stove. I've seen it. It doesn't end well.
The technique: Hold the cigar at a 45-degree angle, about an inch above the flame. Rotate it slowly, toasting the entire foot until you see a faint orange glow across the surface. This should take 10 to 15 seconds. Don't let the flame touch the tobacco directly—you're charring it, not incinerating it.
Once the foot is evenly toasted, bring the cigar to your lips and take a few slow, gentle puffs while holding the flame near (but not touching) the foot. You should see the tobacco ignite evenly across the entire surface. If one side lights up more than the other, keep rotating and puffing until it's even.
Check your work by gently blowing on the foot. The lit area should glow evenly across the entire circle. If there's a dark spot, keep toasting.
How to Smoke a Cigar
Here's the single most important thing you need to know about smoking a cigar: Do. Not. Inhale.
Cigars are not cigarettes. The smoke is meant to stay in your mouth, where you taste it, and then you blow it out. If you inhale it into your lungs, you will cough, you will feel nauseous, and you will immediately regret your choices. Cigar tobacco is strong—much stronger than cigarette tobacco—and your lungs are not prepared for it.
Instead, take a slow, gentle draw (like sipping through a straw), hold the smoke in your mouth for a moment, and then exhale. You're tasting the smoke, not absorbing it.
Puffing cadence: A good rule of thumb is one puff every 30 to 60 seconds. Too fast, and the cigar overheats, turning the flavor bitter and harsh. Too slow, and it goes out. Find a rhythm that keeps the cigar lit without turning it into a chimney.
If you're new to cigars, you might feel a slight nicotine buzz after 20 or 30 minutes. That's normal. If you feel lightheaded or queasy, slow down, drink some water, and eat something. A full stomach helps.
Letting it rest: You don't need to puff constantly. A well-made cigar will stay lit for a minute or two between puffs. Set it down in an ashtray, let it rest, and pick it back up when you're ready. This is not a race.
Retrohaling: Once you're comfortable with the basics, try retrohaling—exhaling a small amount of smoke through your nose. It sounds intense, but it's the best way to experience the full range of flavors in a cigar. Your nose has way more taste receptors than your mouth, and retrohaling opens up notes you'd otherwise miss. Start with just a tiny bit of smoke. You're not trying to blow smoke rings out of your nostrils; you're gently exhaling a wisp through your nasal passage.
Pairing Your Cigar
A cigar is good on its own, but a cigar with the right drink is better. The goal is to find a pairing that complements the flavors without overpowering them.
Bourbon is the classic choice for a reason. The caramel, vanilla, and oak notes in a good bourbon play beautifully with the earthy, leathery, slightly sweet flavors in most cigars. A robusto and a pour of Elijah Craig Small Batch is one of the great pleasures in life.
Scotch works if you're smoking something with more body. A peaty Islay scotch with a full-bodied maduro is either a match made in heaven or a smoky war zone, depending on your palate.
Coffee is underrated. A strong espresso or a dark roast pairs incredibly well with a morning cigar, and it won't interfere with the flavors the way a sugary soda might.
Avoid anything too sweet or too acidic. A margarita or a Coke will drown out the subtleties of the cigar. Stick with something that has depth and complexity.
Common Mistakes (And How to Avoid Them)
Smoking too fast. This is the #1 mistake new cigar smokers make. If your cigar is hot to the touch or the smoke tastes bitter, you're puffing too often. Slow down. Let it rest. A cigar should be relaxing, not stressful.
Relighting etiquette. If your cigar goes out, don't panic. It happens. Just knock off the ash, blow through the cigar to clear out any stale smoke, and relight it using the same toasting technique you used the first time. If it's been out for more than 10 or 15 minutes, the stale smoke might make it taste bitter. You can still relight it, but the flavor won't be as clean.
Biting the cap. Unless you're a character in a Western, don't do this. Use a cutter. Always.
Dipping the cigar in whiskey. I've seen people do this, and I have no idea where they learned it. It does not improve the flavor. It makes the wrapper soggy and ruins the burn. If you want the flavors to mix, sip your whiskey between puffs.
Ashing too often. You don't need to flick the ash every 30 seconds. A good cigar will hold an inch or more of ash before it naturally falls off. Letting the ash build up actually helps regulate the temperature and keeps the burn even. Just let it fall when it's ready.
How to Store Cigars
If you're only buying one cigar at a time, you don't need to worry about storage. But if you're planning to keep a few on hand, you need to know the 70/70 rule: 70% humidity, 70 degrees Fahrenheit. This keeps the cigars fresh and prevents them from drying out or getting moldy.
A traditional humidor is great if you're serious about cigars, but for beginners, I recommend the tupperdor hack: Buy an airtight Tupperware container, toss in a Boveda humidity pack (the 69% pack is perfect for long-term storage), and you're done. It costs $10, it works flawlessly, and it doesn't require any maintenance.
Boveda packs are two-way humidity control, meaning they add moisture when it's too dry and absorb it when it's too humid. You literally just throw them in with your cigars and forget about them for a few months. When they start to feel crunchy, replace them.
Do not store cigars in the fridge. Do not leave them in your car. Do not put them in a Ziploc bag and hope for the best. If you're going to spend money on good cigars, spend $10 on a tupperdor and keep them fresh.
You're Ready
Smoking a cigar isn't about impressing anyone or following some elaborate ritual. It's about slowing down, paying attention, and enjoying something that's been crafted with care. You don't need to know the difference between ligero and seco to enjoy a good cigar. You just need to know how to cut it, light it, and not inhale it.
Start with a mild robusto, take your time, and don't overthink it. If you mess up, laugh it off and try again. I once accidentally torched half the wrapper off a $15 cigar in front of a guy who turned out to be a tobacconist. He didn't judge me. He just handed me another cutter and said, "Try again."
If you're looking for specific recommendations, check out our list of the top 10 cigars worth smoking or browse our full cigar reviews and guides. And if you're still figuring out what you like, that's the whole point. Light one up, pour something good, and see where it takes you.
