Your bag is empty.
Smoking a cigar can celebrate a lot of different things in life, from your favorite team winning a championship to finding out that you’re going to be a parent. Whatever the occasion, you want to be prepared for the moment and know how to properly savor your stogie. It’s why we asked Playboy Bunny Taylor Gallo, along with Kingmakers Cigars COO Claudio Torres and the folks at Cigar Club Miami, to be our Playboy Advisor and answer your biggest questions related to cigars.
I’ve never smoked a cigar in my life, but I want to start. I don’t want to look like an idiot the first time I light one up with the guys. What do I actually need to know before I walk into a cigar shop?—Jim S., Chicago
You don’t need to know everything, just a few things that matter.
Expect to spend somewhere between $10 and $25 for a solid first cigar. Stay in that range and you’ll be in good hands. Start with something mild to medium, not the darkest cigar in the room. Stay in that range and you’ll be in good hands, without trying too hard.
If you’re unsure, ask the tobacconist. A good one will guide you quickly, they do this all day. Some shops have lounges you can use to smoke then and there. Take advantage of the space and smoke and spark up conversations with fellow smokers, they would love the chance to give you their thoughts on the best starter cigar.
Take slow draws, don’t inhale, and give it time. That alone will set you apart.
I’ve heard cigars described using words like “body,” “draw,” and “finish.” I nod along like I understand, but I genuinely have no idea what any of that means. Can you break it down?—Dustin L., Albuquerque
Body is the strength … how full or light it feels when you smoke it. The draw is how easily air moves through the cigar. Too tight and it’s work, too loose and it burns too fast. And the finish is what lingers after each puff… the part you actually remember.
Is there a real difference between a $10 cigar and a $50 cigar, or is it mostly just status?—Linda B., Providence
There can be a difference, usually in construction, aging, and consistency.
More expensive cigars are often rolled with more precision and aged longer, so they burn cleaner and taste more refined. But price doesn’t guarantee anything.
There are cigars in the $15–$25 range, like the Playboy x Kingmakers Habano, that are blended to be approachable, balanced, and well-constructed without overcomplicating the experience.
A well-made $12 cigar will always beat a poorly made $50 one.
I smoked a cigar at my buddy’s wedding and spent the right of the night green in the face. What did I do wrong, and how do I make sure that never happens again?—Ben F., Bloomington, Ind.
You probably smoked too fast or on an empty stomach. Nicotine hits harder than people expect, especially if you’re new. Eat first, take slow draws, and don’t treat it like a cigarette.
If you start to feel off, stop. Put it down. There’s no reward for pushing through it, even if you have to take a little heat form your buddes.
I want to start buying my own cigars instead of bumming them off people. What should I actually be looking for when I walk into a shop? Is there a way to tell if a cigar is good before I buy it?—Greg B., Philadelphia
Look at the wrapper first. It should be smooth, with minimal veins and no cracks. Give it a gentle squeeze—it should feel firm with a little give, not dry or spongy.
If you’re unsure, ask. A good shop will guide you better than guessing ever will.
If you’re shopping online, stick to reputable retailers like cigars.com and pay attention to how cigars are stored and shipped. Look for clear photos, proper descriptions, and avoid anything that looks dried out or discounted for the wrong reasons.
I’ve heard you need a humidor. Do I really need one, or is that just something cigar snobs say? And if I do need one, what’s the minimum I should spend?—Tom S., Portland, Ore.
If you’re keeping cigars for more than a few days, you need one. They should sit around 65 to 70 percent humidity. Outside of that, they start to lose their character. It doesn’t have to be expensive. A small desktop humidor or even a sealed container with humidity packs works if it’s consistent.
If you want something simple and reliable, a Boveda pack setup or an entry-level desktop humidor from brands like Xikar or Daniel Marshall is a solid place to start.
A good humidor can cost anywhere from $50 to thousands of dollars. Choose something that fits your space and your pace.
I have a few cigars I want to display in my home office—I think it looks cool and sophisticated. What’s the best way to display them without ruining them?—Cody J., Denver
You can display them … just don’t leave them exposed. Air dries them out faster than people think, and once that happens, the experience is gone. Use a humidor or a sealed display case. That way they still look good … and smoke the way they should.
What’s the etiquette on re-lighting a cigar? If I put one down and come back to it an hour later, is that disgusting or totally normal?—Randy P., Knoxville, Tenn.
It’s completely normal. Tap off the ash, gently toast the foot again, and bring it back slowly. If it turns harsh or bitter, it’s better to let it go and start fresh.
I want to offer cigars to guests at a party I’m hosting. Is there a right way to do that, or do I just put a box out and let people help themselves?—Amy D., San Antonio
Offer a small range… something mild, something medium, maybe something with a little more strength.
Keep cutters and a lighter nearby so no one’s guessing. And let people choose. That’s part of the experience.
Everyone says whiskey and cigars go together, but I don’t love whiskey. Are there other drinks that pair well with a cigar, or is the whiskey thing basically mandatory?—Matt B., Tampa
Whiskey isn’t mandatory. It’s just the default. Coffee, rum, tequila, even wine and champagne can pair really well depending on the cigar. You’re looking for balance … something that complements the cigar, not competes with it. Experiment and enjoy without any preconceived notions. I’ve even enjoyed cigars with a spicy hot chocolate. Espresso Martinis are also a hit and give the cigar a satisfying, cool finish.
I want to take a woman I’m seeing out for cigars and drinks. It feels like a very coo, old-school date idea—but I also don’t want to come off like I’m trying too hard. What’s the move?—Roger C., New York
A cigar lounge can work, but only if it feels open, welcoming, and not like a room full of regulars who all know each other. The wrong lounge can feel insular fast.
If you are unsure, a great bar or restaurant with an outdoor space is often the better move. It keeps things lighter, gives you flexibility, and lets the cigar be part of the night, not the whole thing.
If you do choose a lounge, go for ones that feel more social than serious. Places like The Stork Club rooftop in Jersey City, Eight Lounge in Las Vegas, or Española Cigar Bar in Miami Beach set the tone without making it feel like you are stepping into a private club.
Keep it simple, guide without overdoing it, and let her find her own rhythm with it.
If she feels comfortable and respected, the rest takes care of itself.