How to Smoke a Cigar: Beginner Step-by-Step Guide | CigarNewbieU


There are certain moments as a photographer when you realize you’re documenting more than a business — you’re capturing a culture.

Recently, I had the opportunity to photograph a branding session for an upcoming online information resource dedicated to cigars called CigarNewbieU. The session took place outside along the Wilmington Riverfront in Wilmington, Delaware, where the calm water, open sky, and relaxed atmosphere created the perfect setting for slowing down and enjoying the moment.

As the owner, Randy Daye, carefully cut, toasted, and lit a cigar for the photos, I realized something interesting.

For something that has been around for centuries, a lot of people actually don’t know how to properly smoke a cigar.

Some people inhale like a cigarette. Others torch the entire thing. Some puff constantly and overheat the cigar. And others simply avoid cigars altogether because they feel intimidated by the process.

But once you understand the basics, cigars become something completely different.

They become slow. Intentional. Relaxing.

They become an experience.

In this guide, I’m going to walk through how to smoke a cigar step-by-step, using what I observed during that branding session along the Wilmington Riverfront, along with tips from seasoned cigar enthusiasts and insights from Randy Daye of CigarNewbieU.

And if you’re completely new to cigars, don’t worry — this article is designed to make the process approachable.


THE CULTURE BEHIND SMOKING CIGARS

Before we talk about how to smoke a cigar, it’s worth understanding something important:

Cigars aren’t rushed.

Unlike cigarettes or vaping, cigar smoking is about slowing down. It’s something people often enjoy during celebrations, meaningful conversations, or moments of reflection.

Historically, cigars have been associated with:

  • Celebrations
  • Business deals
  • Weddings
  • Births
  • Relaxation after a long day
  • Sharing time with friends

During the branding session I photographed at the Wilmington Riverfront, Randy shared something that stuck with me.

He explained that cigar smoking is deeply personal.

As Randy puts it:

“Smoking a cigar is a personal thing. Nobody can say you did this wrong or you did that wrong, it’s completely up to the cigar holder. Cigar smoking, tasting notes, and pairings come down to the individual. That’s what makes it a beautiful thing, for me there really is no right or wrong way, just properly and improperly.”

That philosophy is really at the heart of cigar culture.

It isn’t about strict rules or perfection.

It’s about enjoying the moment and discovering what you personally enjoy.


THE STORY BEHIND CIGARNEWBIEU

Part of what made this branding session special was hearing the story behind CigarNewbieU.

Randy Daye is a native of Neptune, New Jersey, and in 2013 he moved to Delaware simply for a change of pace. That same fall, a high school friend who was already living in Delaware reintroduced him to cigars.

What began as two friends enjoying an occasional cigar quickly grew into a hobby — and before long, a true passion.

As time went on, Randy’s curiosity about cigars deepened. He became driven to learn more about blends, brands, and the craft behind them, always searching for cigars he had never tried and experiences he had yet to discover.

As Randy describes it:

“What started casually has turned into a journey of knowledge, connection, and appreciation. The rest is pure magic.”

That curiosity eventually led to the creation of CigarNewbieU, a resource designed to help people learn about cigars without feeling overwhelmed.

And honestly, that mission came through clearly during the photoshoot.

This wasn’t about showing off expertise.

It was about making cigar culture approachable.

Learn more about CigarNewbieU here


Randy Daye from CigarNewbieU sitting on a bench at the Wilmington Riverfront demonstrating how to smoke a cigar properly.

Randy Daye of CigarNewbieU demonstrating proper cigar smoking technique during a branding session at the Wilmington Riverfront in Wilmington, Delaware.

WHAT MAKES A CIGAR DIFFERENT FROM A CIGARETTE


Many beginners make the mistake of assuming cigars are simply larger cigarettes.

They’re not.

There are several key differences.

  1. Cigars are made from whole tobacco leaves
  2. Cigars use long-filler tobacco leaves that are aged and rolled together. This creates a more complex flavor profile compared to shredded tobacco found in cigarettes.
  3. Cigars are not inhaled
  4. This is one of the most important differences. Cigar smoke is meant to be drawn into the mouth and tasted, not inhaled into the lungs.
  5. Cigars burn slower
  6. A good cigar can last anywhere from 30 minutes to over an hour, depending on its size.
  7. Cigars are about flavor
  8. Cigar enthusiasts often describe tasting notes such as cedar, coffee, chocolate, earth, spice, leather, and cream.

During the branding session at the riverfront, Randy described cigars almost like wine. Different blends, wrappers, and aging processes create entirely different experiences.


THE ANATOMY OF A CIGAR

Before learning how to smoke one, it helps to understand the parts of a cigar.

  • Wrapper: the outer leaf that gives the cigar much of its flavor and appearance
  • Binder: the leaf that holds the filler tobacco together
  • Filler: the blend of tobacco leaves inside the cigar
  • Cap: the sealed end of the cigar that you cut before smoking
  • Foot: the open end of the cigar that you light

Understanding these parts helps you appreciate how much craftsmanship goes into every cigar.


STEP 1: CHOOSING THE RIGHT CIGAR FOR BEGINNERS

One of the first things beginners ask is: What cigar should I start with?

If you’re new to cigars, starting with something too strong can make the experience unpleasant.

A good beginner cigar is typically:

  • Mild to medium strength
  • Smooth
  • Balanced
  • Not overly large

Many cigar shops will happily recommend beginner-friendly cigars if you ask.

Size also matters. Larger cigars last longer, but they can be overwhelming for a first experience. A shorter cigar is often the best place to start.

Randy explained during the photoshoot that part of the fun is simply trying new cigars and seeing what you like.

There is no universal “best” cigar.

Only the best cigar for you.


STEP 2: CUTTING THE CIGAR PROPERLY

Before smoking a cigar, you must cut the cap. This allows air to flow through the cigar when you draw.

There are several ways to cut a cigar:

  • Straight cut: the most common and beginner-friendly cut
  • V-cut: creates a wedge shape that concentrates the smoke
  • Punch cut: creates a small hole in the cap

During the branding session, I watched Randy carefully cut the cigar just above the cap line.

Cutting too much can cause the cigar to unravel.


STEP 3: TOASTING THE CIGAR

One of the biggest mistakes beginners make is lighting a cigar like a candle.

The proper method is called toasting.

Toasting prepares the tobacco evenly before lighting.

Hold the flame slightly away from the cigar’s foot. Rotate the cigar slowly while warming the tobacco. This helps the cigar burn evenly once it’s lit.




Close up of cigar smoke while Randy Daye demonstrates proper cigar smoking technique.

Randy Daye of CigarNewbieU enjoying a cigar and demonstrating proper cigar smoking technique during a branding session.

STEP 4: LIGHTING THE CIGAR

Once the foot is toasted, it’s time to light it.

Bring the cigar to your mouth and gently draw while continuing to rotate the cigar near the flame. You want an even burn across the entire foot.

Randy shared a tip during the photoshoot that beginners often overlook. He recommends using a soft flame lighter or even a cedar spill.

As he explained:

“To really enjoy the experience try lighting with a soft flame lighter or a cedar spill (a thin strip of cedar). It takes a little longer to light and it takes practice.”

That slower lighting process actually enhances the experience.

It forces you to slow down and enjoy the ritual.


STEP 5: HOW TO PUFF A CIGAR

Unlike cigarettes, cigars are not inhaled.

Instead, draw the smoke into your mouth and release it.

Think of it more like tasting the smoke rather than breathing it in.

Most cigar smokers take a puff about once every 30–60 seconds.

Puffing too frequently overheats the cigar and can make it taste bitter.


STEP 6: UNDERSTANDING THE FLAVOR

As the cigar burns, the flavor evolves.

Cigar enthusiasts often talk about the three thirds of a cigar.

  • First third: lighter, more subtle flavors
  • Second third: deeper, more complex flavors develop
  • Final third: the cigar often becomes richer and stronger toward the end

This evolution is part of what makes cigars fascinating.


STEP 7: LETTING THE ASH BUILD

A well-made cigar can hold a long ash.

Allowing the ash to build helps regulate temperature and maintain an even burn.

When the ash naturally becomes long or unstable, gently tap it into an ashtray.


STEP 8: KNOWING WHEN TO STOP

Cigars are not smoked to the very end.

Most smokers stop when about one to two inches remain, or when the cigar becomes too warm or strong.

And here’s another helpful detail: you don’t stub out a cigar like a cigarette.

Instead, simply place it in the ashtray and let it go out naturally.



Close up of Randy Daye holding a cigar and blowing smoke while demonstrating proper cigar smoking technique.

Randy Daye of CigarNewbieU demonstrating proper cigar smoking technique during a branding session.

COMMON BEGINNER MISTAKES

Even experienced smokers once made these mistakes:

  • Inhaling the smoke (don’t — cigar smoke stays in the mouth)
  • Puffing too quickly (overheats the cigar and turns it bitter)
  • Using the wrong lighter (a clean soft flame is often best)
  • Overcutting the cap (can unravel the wrapper)


PAIRING CIGARS WITH DRINKS

Many cigar smokers enjoy pairing cigars with drinks. Popular pairings include:

  • Whiskey
  • Bourbon
  • Rum
  • Coffee
  • Espresso

But as Randy shared earlier, cigar smoking is personal — and pairings are too.

What tastes perfect to one person may be completely different for someone else.

That’s what makes it a beautiful thing.


THE SOCIAL SIDE OF CIGARS

One thing I noticed while photographing the branding session along the Wilmington Riverfront was how social cigars are.

People gather around them.

Conversations slow down.

Phones get put away.

There’s something about the ritual that encourages people to connect.


WHY PEOPLE LOVE CIGARS

Cigar smoking isn’t just about tobacco.

It’s about:

  • Craftsmanship
  • Tradition
  • Relaxation
  • Flavor
  • Community

For some people it’s a celebration.

For others it’s a moment of quiet after a busy week.

For me as a photographer, it’s also incredibly visual — the glow of the foot, the curl of smoke in open air, and the calm vibe that comes with slowing down.


Randy Daye from CigarNewbieU enjoying a cigar outdoors at the Wilmington Riverfront in Wilmington Delaware.

Randy Daye demonstrating how to smoke a cigar while enjoying a cigar outdoors in Wilmington Delaware.

FINAL THOUGHTS: CIGARS ARE MEANT TO BE ENJOYED SLOWLY

If there’s one thing I learned while photographing this branding session along the Wilmington Riverfront, it’s this:

Cigars are meant to be enjoyed slowly.

They’re not rushed.

They’re about the experience.

Watching Randy sit by the water, take his time lighting the cigar, and simply enjoy the moment reinforced something that often gets lost in a fast-paced world.

Cigar culture encourages people to slow down.

To enjoy conversation.

To appreciate craftsmanship.

And sometimes just to sit quietly and enjoy the moment.

And that philosophy is exactly what CigarNewbieU is built around — helping people discover cigars in a way that feels approachable and enjoyable.


LEARN MORE ABOUT CIGARNEWBIEU

CigarNewbieU was created by Randy Daye to help people explore the world of cigars without feeling overwhelmed.

His journey from casually smoking cigars with a friend to becoming passionate about the craft is exactly what inspired the platform.

Learn more here


ABOUT THE PHOTOGRAPHER

I’m a photographer based in Newark, Delaware, specializing in branding photography for businesses and entrepreneurs.

My goal with every branding session is simple:

To capture the personality behind the brand.

Because the most powerful marketing doesn’t just show what a business sells.

It tells the story behind it.



If you’re building a business and want images that truly reflect your brand, a professional branding session can make all the difference. Whether you’re launching something new like CigarNewbieU or refreshing the look of an established business, the right photos help tell your story and connect with your audience. If you’re ready to elevate your brand with authentic, storytelling-driven imagery, I’d love to work with you.  Fill out the inquiry form and tell me a little about your business and vision for your branding session. Let’s create something that represents who you are and what you do best.