1. You need proper planning before venturing to Cuba 

Nowadays, technology has made it a lot easier to go on a holiday without doing too much research. As long as you have internet on your phone you can pretty much do the research and plan on the go. It’s easy to get around with Google Maps and find good places for food and entertainment on TripAdvisor. However, in Cuba you don’t get that luxury. There is no 3G or 4G and Wifi is not widely available. Wifi is only available in certain hotels and parks and you need a special internet card that can provide you, for a cost, with a username and a password you can use to access the world wide web. If you don’t plan properly you will waste  time and money trying to find places or the information you need.   

So, before booking flights to Cuba make sure you do your homework and plan as much as possible. Plan accommodation, (either casas particulares or hotels) activities and travel and budgeting. You will definitely not regret it.  

2. Old Havana is a tourist trap 

Pretty much everything in Old Havana has been designed for tourists. Not only are prices ridiculously high but also you can barely see any locals in restaurants and bars to the point that nothing seems authentic anymore. Remember those ads you see in travel brochures depicting locals dancing salsa on the streets of Old Havana? Well, replace those locals with middle Aged European or American Tourists. The only locals you will see (apart from the bar staff) will be sitting around in parks or trying to sell you something on the streets. At night things might take a turn in some places. For example, I went to a ‘famous’ Salsa Dancing Club in Old Havana and I was actually the only foreign male there. But there was no local woman either. The only people dancing were the local Cuban guys dancing with their white foreign girlfriends. More than just a bit disappointed, I stroke a conversation with one of the guys at the bar and asked him where I could get a taste of the real dancing scene and was directed on the outskirts of Havana, away from the tourist trap.  

The problem was that, for a tourist, getting a taxi there was ridiculously expensive (about $30 one way) and the only feasible way for me was getting a ‘shared local cab’ – that basically meant hitchhiking. Although I speak Spanish and I’m quite adventurous, after one day of dealing with the constant anxiety of being deceived, hitchhiking to the outskirts of Havana and back at night was the last thing I wanted to do.  

Vedado is a way better option than Old Havana. While still quite touristy, prices are a lot lower and you get a lot of locals in the bars and clubs.   

3.There is a perpetual sense of anxiety on the streets 

Tourists are constantly harassed by locals who either want to sell them fake cigars, rum, or take them to some private restaurant (aka a random house) where they can pay for a meal. In Central Havana, I was constantly approached by young men trying to convince me there was a Cuban Cigars Festival ending soon which I definitely had to see where I could buy super discounted original cigars. Of course, the so-called festival happened indoors, in random houses, where several individuals sold counterfeit cigars. Out of sheer curiosity I did buy a box of 20 from one of them for 40 dollars (which I negotiated down from 100 he was asking) and they were terrible.  On the other hand, I did go to a so-called private restaurant (unaffiliated to the government), where the food was a lot better and three times cheaper than in restaurants in Old Havana. 

The paradox is that some of these ‘harassers’ actually have genuine good intention and you can definitely have a positive experience. However, things can go the other way as well.  The problem is that this constant harassment creates a tension and anxious feelings on the streets I’ve never experienced before as a solo traveller. You simply don’t feel you can trust what anyone says and you are sceptical of everything that comes your way. Since hostels are not really a thing in Cuba, solo travellers are on their own most of the time and find it hard to even interact with each other. Since there’s no mobile internet and Wifi is really hard to find and get, I’ve tried to approach other travellers to ask for directions or advice but I felt I hit a barrier I’ve never felt before in my 10 years of solo travelling. All the other travellers were sceptical of me asking them questions and one even refused to take a picture of me using my own phone when I politely asked him to do so. (Read more about my personal experience on this particular aspect here

4. There is a divide between locals and tourists 

Partly because some locals will harass tourists and partly because some locals will speak too much against communism, the police prefer to see the tourists and locals separated. Unless of course, the tourists are buying services by government-run or affiliated businesses. Not only have I been told this by the locals I’ve met in Havana and by my Cuban friends but I’ve also experienced it myself. I was having one random conversation with a local in the park in Spanish when out of the blue the police came over and asked for both of our ids. When they realised that I was a tourist, they asked me why I was talking to the local. I responded that I was asking him for directions and they just took him away. When I asked them why they were taking him away I was told to mind my own business.  

As there are many locals that either try to scam you or sell counterfeit products on the streets there is a rationale behind the police’s actions but it is definitely overly aggressive.  

5. Spanish can be both an advantage and a disadvantage

Speaking Spanish can be a huge advantage in Cuba as it can facilitate asking for directions, negotiating and getting around. Also, Cuba uses two types of currencies : the CUC, designed for tourists (Peso Convertible) and the CUP, the one for the locals. (Peso Cubano) One CUC is worth about 30 CUPs but they are used for different services and items. For example in some places I’ve been the prices of food were shown in Pesos only. The menu did not indicate whether it was local or convertible ones. Tourists would pay in convertible pesos (30 times more!) while locals or Spanish speakers like myself in local ones. If you don’t speak Spanish it’s a lot harder to get your hand on CUPs or even use them.

However, Spanish can also be a disadvantage when dealing with scammers. Sometimes scammers’ English might not be good enough to convince you to fall for their schemes but if you speak their language, it will be a lot easier for them to do so.

6. Nothing is for free 

If you stand out as a tourist, it’s almost guaranteed that most people will encounter will want your money or clothes from you. And this is understandable, since wages are extremely low in Cuba and basic commodities for Westerners such as toothbrushes, clothes and shoes are hard to obtain for the average Cuban. However, once you can put yourself in their shoes everything starts making more sense and conversations become easier. Some locals might ask you for money in exchange of them showing you a good time around local clubs or in exchange for genuinely teaching you about the Cuban way of life.  As I have experienced, this can go either way, as it’s hard to know who to trust so choosing to trust a random local that approaches you on the street is taking a risk.  

However, for a risk-free, but more pricy option, I would definitely recommend AirBnb Experiences. I booked two of them and could not be more content I did: A tour of Central Havana with an economics student who explained how ‘street economy’ worked in Cuba; and a photography tour with a photography student, who took me around the best spots of old Havana and took some great shots of me. Each 4-hour tour cost me about 35 dollars.  

7. People will surprise you 

I have encountered people who completely shattered my negative impression and sceptical mindset of the local Cubans. One random person I stroke a conversation with in a park offered to show me a glimpse of his local food culture (Copella) and he insisted he paid for everything. He didn’t ask for a single penny in return. On other hand, some locals I had known for a couple of days who pretended to be my friends, turned around and deceived me. (read story here)

Also, women are extremely straightforward. If you look someone in the eyes, if they are interested in you, they will maintain that eye contact until you say something. If you don’t, they will ask you what your deal is.  

8. If you want to taste the real Cuban culture, you need to take risks 

Going to Cuba and staying in a hotel or resort is simply not worth it because you will not get a real understanding of the Cuban culture. Moreover, you will also pay hyper-inflated prices. There are far cheaper and more luxurious options if you want to enjoy the Caribbean coast.  

However, if you want to really get an understanding of the culture, you need to take some risks. Risks include: staying in private accommodation (casas particulares) where conditions might not be up to Western standards; eating at private restaurants (basically local homes) where you are not guaranteed the hygiene standards you might be in a restaurant; trusting locals to show you around or sell you products as some might deceive you.  

If you are not prepared to take at least one of these risks, then you would be better of spending your money somewhere else.  

For a more detailed account of my experience in Havana you can check out the following posts:  

Part 1: Havana Hustlers Club
Part 2: The Right Place with the Wrong People
Part 3: Everlasting Cuba