Easily one of the strangest-looking stogies on the shelf, and perhaps the most misunderstood, is the crazy-ass concoction that is the "culebra" cigar vitola. Translated from Spanish, culebra merely means snake, which makes complete sense when you look at the writhing outline that the cigar forms.

But this isn't a single stogie, but typically a trifecta of slender smokes all bound together. Commonly constructed from anywhere from two to four super slender panetela cigars, the average culebra looks more like a braided knot of roots than a premium tobacco product. However, the classic culebra can be quite elegantly done in certain circumstances and has its own unique smoking merits. 

But how are these types of cigars rolled? Why were they created in the first place? Do culebra cigars provide any additional stogie smoking perks? Who offers a good culebra nowadays? And how in the hell are you supposed to smoke one of these things anyway? 

Well, allow us to elaborate, and let's stop slithering around the subject, shall we?

How Did the Culebra Cigar Vitola Get Started?

Like many aspects of cigar manufacturing history, the exact geographic location and factory where the culebra was first produced remains shrouded in mystery. All we know is that references to this cigar vitola first began to materialize in newspapers in the early 1880s and that it was a bit of an obscure hit with certain cigar smokers for nearly half a century. 

While it isn't clear as to where the culebra was first rolled, and why it was created in the first place, there are some theories on the matter. Some say it occurred in Cuba, where cigar factory workers were allowed three cigars a day for personal consumption. To make sure the employees weren't puffing the primo stuff or more than their daily allowance, a standout cigar style had to be crafted to prove that only "factory smokes" were being torched. This makes complete sense, for there is no mistaking a culebra for another cigar on the shelf, and would have allowed floor managers to easily hand-out three cigars at once to each employee at the start of their shift.

However, there is no written evidence that we can find proving this claim, which leads us to the more irrefutable assertion that this twisted vitola was first produced in the Philippines of all places. According to a report from Holt's on the subject, An Illustrated Encyclopedia of Post-Revolution Havana Cigars explains that the appearance of culebra cigars from the Philippines in newspapers in the 1880s is the first recorded written proof of the vitola's existence. So while the whole daily allotment of three cigars per employee hypothesis does seem logical, so too does the claim that the bound nature of the vitola helped humidity regulation in this tropical country and made packaging bundles easier. 

Whatever the reasoning or backstory, cigar boxes marketing the American-made culebra started showing up shortly thereafter, and by the early 1900s, almost all cigar smokers were familiar with the vitola and had likely smoked one at some point or another.

Culebra Production Explained

Regarding culebra production, the whole process starts with a trifecta of slender panetela cigars that have been slightly underfilled. Due to the lack of tobacco inside, these slender smokes are far more pliable, and therefore can be easily braided. Additionally, the cigar tobacco is a touch more damp than usual, thus making production easier while reducing the risk of a ripped wrapper or cracked binder. 

Once rolled, the cigars are bound together on one end and then braided downward from there until the entire length of the bundle is intertwined. After that, it's on to binding the bottom with a matching piece of twine, ribbon, cigar band, or stray tobacco scrap so that the bundle stays straight. As the clump of twisted cigars age, and the overly damp tobacco dries, the bindings on each end help keep the culebra from coming apart. Additionally, vegetable gum, fruit pectin, or potato starch are commonly used to help keep the outer wrapper leaves in tight form, just like any other form of premium cigar blend.

How to Smoke a Culebra Cigar (The Right Way)

While it is possible to cut and spark all of the cigars at once, smoking an entire culebra bundle in one sitting is just asking for a massive, flaky mess. Not only will you have to contend with keeping track of the burn line on multiple cigars simultaneously, but ash tends to go everywhere when the cigars converge. There's also a really good chance that one, if not all of the cigars will burn at different rates. And then there is the subject of excessiveness. That's a whole ton of tobacco for one sitting, so best prepare for a fat-ass smack of nicotine while you are at it.

The easiest, and best way to smoke a culebra cigar is to unbind the lot, carefully separate each smoke, and then either place the remaining sticks back in the humidor or hand them out to whoever might be joining you for a stogie session. Due to being a bit underfilled and slimmer in circumference, you may find that culebra cigars will burn a bit quickly. This is perfectly fine, as this tends to be the norm with most panetela cigars. 

Just don't forget to snap a selfie, because chances are you will look goofy as all hell with a gnarled cigar that resembles a tree root poking out of your pie hole. 

Parting Puffs

Nowadays, culebras are more of a fun alternative to smoking a "straightforward" cigar than a habitual stogie option. Not only is a culebra a challenge to transport, but it is also wacky as can be and can be a challenge to smoke. So like massive ring gauge cigars, this sort of smoke is typically considered to be more of an amusing curiosity or a gag gift than a bona fide connoisseur's smoking option.

That's not to say that a culebra isn't a ton of fun though, and it sure does make for a great surprise for your buddies when you tell them that you brought stogies for everybody.