Cigars have long been associated with sophistication and class, and for good reason. A well-crafted cigar can be a true pleasure to smoke, offering a variety of flavors and aromas that can be enjoyed and savored over time. But for the uninitiated, cigar smoking can be a bit intimidating. In this Millennial Gentleman Guide, we’ll walk you through the basics of cigar smoking, from choosing the right cigar to lighting and smoking it like a true gentleman.

The History of Cigar Smoking

Cigar smoking has a long and storied history that dates back to ancient civilizations. The Mayans and Aztecs are believed to have been the first to cultivate tobacco and roll it into cigars. They used cigars in religious and ceremonial contexts, and they also believed that cigars had medicinal properties.

When Christopher Columbus and his crew arrived in the Caribbean in 1492, they encountered the indigenous people smoking cigars. The sailors brought tobacco back to Europe, where it quickly became popular among the upper classes. In the 16th century, cigar smoking spread to Spain, where it was enjoyed by the wealthy and the royal courts.

As the popularity of cigars grew, so did the demand for tobacco. In the 18th century, tobacco cultivation and cigar production became a major industry in countries like Cuba, the Dominican Republic, and Nicaragua. In the 19th century, cigar smoking became a symbol of status and wealth, and it was enjoyed by politicians, business leaders, and celebrities.

In the 20th century, cigar smoking faced a decline in popularity due to health concerns and the rise of cigarette smoking. However, in recent years, cigar smoking has seen a resurgence in popularity, particularly among younger generations. Many people are now rediscovering the pleasure of a well-crafted cigar and the ritual of smoking it.

Today, cigars are enjoyed by people of all ages and backgrounds, and they continue to be a symbol of luxury and elegance. The history of cigar smoking is a rich one, steeped in tradition and steeped in the culture and customs of many different civilizations.

The Different Types of Cigars

First and foremost, let’s talk about cigar types. There are two main types of cigars: machine-made and handmade. Machine-made cigars are mass-produced using machines, while handmade cigars are made by skilled artisans using traditional methods. Handmade cigars are generally considered to be of higher quality and offer a more complex and nuanced smoking experience.

When choosing a cigar, it’s important to consider the size and shape of the cigar. The most common sizes are:

  • Petit Corona: 4.5 inches by 42 ring gauge
  • Corona: 5.5 inches by 42 ring gauge
  • Robusto: 5 inches by 50 ring gauge
  • Toro: 6 inches by 50 ring gauge
  • Churchill: 7 inches by 48 ring gauge
  • Double Corona: 7.5 inches by 49 ring gauge

The ring gauge refers to the cigar’s width, and the larger the ring gauge, the more smoke and flavor you can expect. However, it’s important to note that a larger ring gauge does not necessarily mean a better cigar.

It’s also important to consider the wrapper, as this can greatly affect the cigar’s flavor and aroma. The most common wrappers are:

  • Connecticut: Light and mild, often used for mild-bodied cigars
  • Cameroon: Medium-bodied, with a slightly spicy flavor
  • Maduro: Dark and rich, often used for full-bodied cigars
  • Habano: Full-bodied, with a spicy and robust flavor

How to Light a Cigar

Once you’ve chosen your cigar, it’s time to light it. This is where many novice cigar smokers go wrong, as lighting a cigar is a bit different than lighting a cigarette.

Cutting the Cigar Tip

Cutting a cigar before lighting it is an essential step in the cigar smoking process, as it allows for proper airflow and a smooth draw. There are several different ways to cut a cigar, but the most common method is to use a guillotine cutter. A guillotine cutter is a small, handheld device that has a sharp blade that slices off the cap of the cigar.

The cap of a cigar is the rounded part of the cigar that is opposite of the foot (the end you light). It’s important to only cut a small portion of the cap, as cutting too much can cause the cigar to unravel and affect the smoking experience. The ideal cut should be about 1/16th of an inch from the cap.

Another way to cut a cigar is by using a punch cutter, which is a small, cylindrical tool with a sharp tip. A punch cutter is inserted into the cap of the cigar and twisted, removing a small circular piece of the cap. This method is a popular alternative to the guillotine cutter and it’s especially suitable for cigars with a tighter draw or those with a closed foot.

It’s important to note that you should never bite off the cap of a cigar, as this can cause the wrapper to unravel and affect the flavor and aroma. Also, you should never use a regular pair of scissors or knife to cut a cigar as it can crush the cigar and ruin the flavor.

In summary, cutting a cigar before lighting it is an essential step in the cigar smoking process. It allows for proper airflow and a smooth draw, which helps to preserve the cigar’s flavor and aroma. The most common method is to use a guillotine cutter or a punch cutter, and it’s important to only cut a small portion of the cap, ensuring not to unravel the cigar or crush it.

Lighting the Cigar Correctly

First, you’ll want to use a butane lighter or wooden match to toast the foot of the cigar. This means holding the cigar just above the flame, but not touching it, and rotating it until the end is evenly charred. This helps to ensure that the cigar will burn evenly.

Next, bring the cigar to your mouth and take a puff while holding the flame to the foot of the cigar. Once the cigar is lit, you can sit back, relax, and enjoy the smoke. Remember, smoking a cigar is not about inhaling, but rather savoring the flavors and aromas. Take your time and enjoy the cigar, puffing every 30 seconds to a minute.

When smoking a cigar, it’s important to remember a few basic etiquette rules. First and foremost, do not inhale the smoke. This is not only bad for your health, but it’s also considered rude. Additionally, be sure to ash your cigar as needed, but avoid over-smoking it, as this can cause the cigar to become too hot and affect the flavor.

Pairing a Cigar with Liquor

Finally, it’s important to pair your cigar with the right drink. A good rule of thumb is to pair a milder cigar with a milder drink, such as a light beer or a gin and tonic, while a full-bodied cigar pairs well with a stronger drink, such as a whiskey or brandy. Of course, this is a matter of personal preference, and you should choose a drink that you enjoy.

In conclusion, cigar smoking is a true gentleman’s pursuit, and one that can be enjoyed and savored for its complexity and nuances. Choosing the right cigar, lighting it properly, and smoking it with good etiquette are all important aspects of the experience. Remember to take your time, relax, and enjoy the flavors and aromas of the cigar. And don’t forget to pair it with a drink that complements the cigar’s flavor profile. With a little bit of knowledge and practice, you’ll be smoking cigars like a true gentleman in no time. Happy puffing!


Carey Martell is Editor in Chief for The Millennial Gentleman. A thirty something modern man who is politically independent, non-religious but a firm believer in ideals of chivalry and traditional family values. Carey lives his life as a vagabond digital nomad traveling and living life to the fullest while managing his businesses remotely with a laptop and internet hotspot connection.