Cuba is the mecca of cigar production. From planting and picking to rolling, cutting and packaging - it's all done in Cuba. So going to Cuba and not buying Cuban cigars would be like visiting the moon and not taking a rock. It's just got to be done.

Even if you don't like cigars, it's worth trying one or two to see if your mind can be changed. Mine was; I hated cigars before I went to Cuba - the taste, the heat, the harshness; it genuinely felt like swallowing poison - but I was chonging like Castro himself by the time I left. The smoothness and freshness of hand-rolled, Cuban cigars makes a hell of a difference.

If you still can't stand cigars after sampling the best Cuban brands, buy some as gifts for friends back home. Trust me, someone will be eternally grateful.

Either way, it's an essential investment to make when you visit the Caribbean's largest and most fascinating island. But if you're going to do it, you better do it properly.

Thus, I bring you the ultimate guide to buying Cuban cigars in Cuba!

How am I qualified to write a guide on buying Cuban cigars in Cuba?

I sampled many Cuban cigars over the course of 3 weeks before stocking up on my favourite brands at the end of the trip. It's fair to say I was a complete novice, and since I'd disliked them so much before the trip I really didn't think I'd be smoking many, and therefore I hadn't done any research. So there was a lot to learn.

But this made the process of discovery even better; learning about how they are made in tobacco plantations, what sets high quality apart from low quality tobacco, the going rate and how to spot the fakes. I learned all this in 3 weeks and by the end of the trip felt more than comfortable choosing which cigars to buy.

Where to start?

It probably won't take long before you are either curious enough to try a cigar or persuaded to try one. They are everywhere and almost everyone smokes them. Seriously, if you tried to explain the dangers of mouth cancer to a cigar-smoking Cuban you'd probably get nothing more than a face full of cloud and a throaty laugh.

So the sooner you start smoking cigars in Cuba the better. Because it's gonna happen.

Start with a smoother cigar, something less harsh than the most popular brands. The Montecristo #2 or Romeo y Julieta are ideal for the novice cigar smoker. Inevitably, they will be harsh – particularly if you don't normally smoke – but tame in comparison to the likes of Cohiba, Bolivar or Partagas.

Thin or fat?

You might wonder about which size of cigar you should get. If you're a novice to cigar-smoking, like I was, I'd say go with thinner cigars to begin with. These are less harsh but harder to toke. Fatter cigars are harsher but you can draw more smoke in. Obviously don't go for the absolute thinnest or fattest available, or you'll overcompensate for one thing or the other, and probably won't enjoy it.

Start with a regular size and work from there.

How much do cigars cost in Cuba?

As you might have guessed, Cuban cigars are a lot cheaper to buy in Cuba than online or anywhere else in the world.

At the time of writing, top quality single cigars could be bought in stores from anywhere between 7-25CUC ($7-25), while boxes of 25 were priced upwards of 120CUC. These prices are five times higher online.

You cannot negotiate the price in cigar stores but you can if you buy on the black market.

Where should you buy Cuban cigars?

Anyone you ask this to will tell you the same thing: buy from the licensed cigar stores, don't buy on the street! ...with the exception of the street vendors, who will almost certainly tell you the opposite.

There are two ways of looking at it: if you want to be absolutely sure you're getting in-date, authentic Cuban cigars, then buy from the stores. Alternatively, if you'd rather buy more for less, and you're willing to take the risk that your cigars could be stale, stolen or even fake, buy from the street vendors.

Buying in Cigar Stores

Buying your Cuban cigars in a licensed cigar store will not only guarantee you quality, but will also allow you more choice, time and freedom to explore. There is no pressure to buy and the store assistants are on hand to answer your questions. English is hit and miss but there's very little they're not used to explaining in detail. For instance, if you want to know more about the type of leaf used to roll the tobacco, the tobacco itself, or how to use a humidor to keep your cigars moist, you shouldn't have any problems.

Cigars are more expensive in the licensed cigar stores, and you cannot negotiate on the price.

Personally, I chose to buy a pack of 3 (Montecristo #2) and two other singles (Romeo & Juliet) from a licensed cigar store in Havana. I couldn't quite stretch the budget to a box of 25 (125CUC).

Buying Cigars on the Street

Inevitably, you will be offered cigars on the street at some point during your trip. Instinct may tell you to just say no and keep walking, and if you're prepared to pay at least 120CUC ($120) per box then you probably should. However, branded cigars sold on the street are not always counterfeit, but they are probably stolen.

It's also not advisable to follow strangers on the street down alleyways and into the building where they are storing the cigars – I actually did this with a friend and although nothing bad happened this is something we later couldn't believe we'd actually done. The guys we met were friendly and all, but had we not decided to buy a box of their cigars who knows how they might have reacted.

We each bought a box of 25 Montecristo #4's for 40CUC ($40), making a saving of about $60.

Buying your Cuban cigars at a Tobacco Plantation

As a great wine is defined by its vineyard, so too is a tobacco by its region. The world's best tobacco is grown in Cuba, which contains four tobacco regions: Pinar del Rio, Partido, Remedios and Vuelta Arriba. Of these, Pinar del Rio is considered to be the best, thanks to its highly fertile soil and higher density of nitrate within the leaves, which produces a stronger, more powerful taste.

So visiting a tobacco plantation in the Pinar del Rio region of Cuba to sample the freshest cigars has become a top priority on most tourists' to-do lists.

After our staple intake of Havana attractions and nightlife, we took the long and dusty road to Viñales, in the small but tourist-packed hub of the Pinar del Rio region. Here we stayed with a Cuban family who arranged a horseback ride of a local tobacco plantation. This lasted around 2 hours and took us through fertile tobacco fields, where we were shown how to pick tobacco, and – after a few rum-sugar cane cocktails and a dip in the river – eventually onto the ranch where it was cut and prepared for distribution to tobacco factories.

At the ranch we were given a lesson in how to roll a cigar using the traditional method. Although we didn't get chance to put our education into practice, we were each given a freshly rolled cigar to puff away on as we learned. This was the best cigar I smoked the whole time I was in Cuba, and the moment I discovered how much better they taste when the toking end is dipped in honey! Seriously, you have to try it.

Before we left we bought a box of freshly wrapped but unbranded Cohibas at a discount price - 15 for 70CUC. They might not have been Cohiba but they'd been so good we couldn't resist!

How to spot the fakes

The truth is, you can never be absolutely sure of a cigar's age or authenticity. But there are a couple of telltale signs:

• There is no warranty seal or the warranty seal does not contain the hologram (righthand side) or bar code (lefthand side).
• The wrappers/bands contain spelling mistakes, wrong colours/fonts or poor alignment.
• There is a glass lid that slides in and out of the box (genuine cigar boxes never have glass tops).
• There is print missing from the underside of the box (every box should say “Habanos S.A., Hecho En Cuba” and "Totalmente a Mano" (made totally by hand), and also state the code for the factory where the cigars were made and the date that indicates when the cigars were packaged.
• The black market price is significantly lower than the regular price (anything more than 100CUC).

What are the best Cuban cigars?

Generally speaking, the most popular Cuban cigars with tourists are the classic Cohibas, Montecristo #2s and the Romeo y Juliet. However, while these might be favoured, there are many others that equal or even surpass them in terms of tobacco quality.

The Winston Churchill-esque Cohiba Esplendido, for example, is a pricey yet high quality cigar that not many tourists come to appreciate. I was fortunate to get my choppers around this one when my host in Remedios shared his with me. It was easily the best I smoked throughout the trip; and even better when we dipped the toking end in a fine Cuban rum! Unfortunately I couldn't quite stretch my budget far enough to afford one (singles are priced at 25CUC) in Havana's Casa del Habano cigar store.

One cigar I definitely wouldn't recommend is the Guantanamera. It tasted and smelled like ashtray before it had even been near one.

So which Cuban cigar should you choose?

If you don't have time to try out a few brands before making your choice, it makes sense that you'd just want to pick the best Cuban cigar brand and be on your way. However, it's not that simple.

What you or your friends will like depends on your/their experience as a cigar smoker. The best-selling Cuban cigars have varying degrees of strength. Partagas and Cohiba, for instance, are stronger, harsher and earthier in flavour, while the Romeo Y Julieta and Montecristo blends are smoother, with a sweeter, nuttier taste.

For me, it was a close tie between the Cohiba and Romeo y Julieta. The Cohiba was stronger, fatter and smoked better; while the Romeo Y Julieta tasted amazing compared to any other cigar I tried. So in the end I bought both and rationed them throughout the rest of my trip in Central America.

Good luck in your quest for your perfect Cuban cigar and believe me, you're gonna have a blast!

This article first appeared on my personal blog, CheekyJaunt.com