It’s probably fair to say that I like to travel dangerously… or if not dangerously, at least without a plan. A few weeks before I flew to Cuba, I was sat chatting to a friend who’d visited numerous times before. He asked me which hotel I was staying at – a question which left me blank.

The concept of booking ahead just feels so alien to me. My usual approach on entering a new country is simply to arrive, pick up a phrasebook, and see what happens. As soon as you try planning something like that, you rule out all the exciting things that could have happened; while hotel comforts often serve to isolate the visitor from the reality of their surroundings.

All that being said however, it would nevertheless be naive of me not to acknowledge the safety net provided in the form of my communication devices and bank card. My arrival in Havana denied me these reassurances, though; and, stepping off the plane with no plans, no contacts and no money, I was forced to experience the city in ways that I had previously not imagined.

The problems all started when my wallet – and everything in it – was stolen in Istanbul. I had travelled by bus from Bulgaria to Turkey, from where I’d fly Istanbul to Moscow, and then finally Moscow to Havana. During my stopover in Moscow I spent every minute on the Internet, frantically chasing up banks, cancelling cards and trying to access my online banking. I was stressed, and I just didn’t have time to check out any travel advice on visiting Cuba. Besides, I had a pocket full of Russian Rubles – which, given the old ties between Cuba and the Soviet Union, I felt confident I’d be able to change once I touched down in Havana’s José Martí International Airport.

Of course, if I had found time to research travel advice I would have learned that Euros and Dollars are pretty much the only currencies a foreigner can change in Cuba. Added to that, Internet is virtually non-existent save for a handful of overpriced business centres in the fancier hotels.

By the time I arrived I was tired and stressed, my wallet was gone, I didn’t speak a word of Spanish and my phone was dead – not that I had anyone to call at this stage, anyway. I had arrived early – I was due to be meeting friends in Havana four days later, but I’d wanted to get a head start and experience a more personal introduction to the city. I would certainly achieve that.

I found the office outside, queueing in the hot sun for what seemed like an eternity, before finally presenting a stack of crisp Russian notes to the money changer. He shook his head. As it turned out, no one in Cuba was prepared to even look at my Rubles.

Reaching a point of desperation, I sat down outside the airport and tried to come up with a plan. For the first while at least, I almost enjoyed the novelty: taxi drivers, illegal money changers and cigar salesmen would approach me for my money – I turned my pockets inside out by way of reply, and asked them for money instead. As the day rolled on though, the situation began to look increasingly bleak… and for a time I wondered if I’d be sleeping on my bench outside the airport for the next four days.

Soon I resorted to striking up conversations with strangers, in the hope of finding help. That’s when I met Marcelo. He was working on a tour desk in the airport, and seemed to be friendly enough.

“I was wondering if you could help me,” I began politely, hesitant at first to reveal quite how much help I was looking for. We got talking and he asked me where I’d travelled from. When I said Bulgaria, he smiled and nodded.

“I know it well,” he answered. I assumed he’d mistaken me; perhaps he’d heard Bolivia, I thought. But Marcelo went on to tell me his story. He was an engineer previously, and as a student he took a three-year work placement with the Soviet Union, to be stationed at an industrial site just south of Moscow. The Party funded an annual holiday for these workers, which usually took them to the beach resorts of Bulgaria.

As Marcelo happily chatted away about his visits to the communist-era monuments at Varna and Buzludzha, I decided to myself this must be fate.

“I need somewhere to stay,” I told him, “but I can’t pay for it.” I explained the stolen wallet, and how I’d be fine once I’d just managed to get to a bank which could change Rubles to Pesos… or failing that, when my friends arrived four days later.

“It’s no problem!” he beamed, “I call my friend. She’ll send a car, she’ll take care of you. Maybe you pay her next week, yes?”

It was dark by the time the unofficial taxi cab arrived. We drove from the airport into the city, along the Malecon, and right into the heart of Old Havana. Here the streets were filled with people and cars, latin music blasting through old speakers and gangs of youths smoking and drinking on corners or sat along the sea wall. I immediately realised I was out of my depth – it was my first time in the Americas and the noise, the chaos of this less-than-affluent district of Havana would offer me no chance to ease myself in gently. When I later gained access to the Internet again, I would read travel sites that advised tourists against walking through these streets after dark… but for me, and for the next four days at least, this was home.

And so began a very strange few days. I found myself living with a local family so nebulous that I never quite managed to pin down who was married to whom, which were whose children, and so on. Some of them were black, others hispanic, and nobody spoke any English.

The door to the small house was always left wide open, onto a street where kids played baseball in the heavy fumes exhaled by classic American cars. My host, Nuria, seemed to be some kind of community matriarch – her home was like an open forum, the whole neighbourhood seemingly welcome to walk in and out without announcement.

During my stay, I got friendly with a young Indian man who had apparently made the same mistake as me – he’d arrived in Cuba without money or support, had been rescued from the streets by Nuria, and thanks to his broken English we were soon laughing about our shared misfortunes and subsequent salvation.

Nuria and her family gave me a room, they fed me, they even gave me lunch money. I would eat meals with them, or sit in a corner studying my Spanish phrasebook, while the women of the house sieved insects out of a sack of state-subsidised rice rations. The socialist nature of Cuba means that citizens are allotted certain quantities of food provided by the state… but as I was to find out, it wasn’t necessarily the best food. Any comforts above merely surviving need to be independently funded – and with local minimum wage running to around $8 per month, it’s easy to understand the importance of tourism here.

Most visitors however, never realise quite how (comparatively) cheap it is to live in Cuba. The country uses two currencies – the “Convertible Peso” is locked to the dollar, and this is what tourists are expected to use. Cuban people however, have access to the “National Peso.” Once I’d picked up a little Spanish I found it relatively easy to get my hands on national currency, and suddenly a meal which might have cost 3 dollars was coming out at more like 30 cents. This dual currency system allows Cuba to milk as much income from tourists as is possible… and who could blame them?

A friend would later tell me that 90% of Cubans want to talk to you; and that 90% of those want your money.

The first part is certainly true. Wherever I went, people would try to strike up a conversation. Most didn’t care that I couldn’t understand much Spanish, while there were many younger people who were desperate to practice the English they’d learned in school. In fairness though, the conversation would usually reach a sales pitch soon enough… but with time to kill and no money to lose, I gave everybody the benefit of the doubt.

I actually love it when people try to scam me. When I was a child I enjoyed nothing better than watching magic shows. The audience queues up, eager to be deceived – and then begins a battle of wits, as the magician attempts to pull some kind of misdirection, while we have to guess the trick, spot the sleight of hand. Being scammed is no different, and any time I travel to a new country I’m always on the lookout for a fresh and unpredictable new routine.

Cuba is not a violent place, and physical attacks on tourists are extremely rare. It may have something to do with an overbearing and punitive big-brother state, which earns a huge amount of revenue from tourism; punishments are severe for citizens accused of assaulting Cuba’s guests. As a result, the criminal classes tend to favour mind games over muggings. They need you to hand your money over willingly… and so by having no money to hand over, I felt as though I’d been given a free pass to every magic show in town.

There was Lazaro, for example, a short hispanic man with gold teeth who stopped me in the street one day and made a lazy attempt to sell me some cigars. The usual pitch is to claim that a family member who works in the cigar factory can smuggle out the good stuff to sell it on the side. They’re fakes, of course, and taste like soggy paper. Lazaro was just going through the motions, the same tired old script, and my attention faded quickly.

Another popular scam here is to ask for help feeding hungry children – and it’s a really emotional pitch. The artiste will often show pictures of their children, then lead the way to a backstreet store which sells plain, white bags of state-issued powdered milk. For a few coins, it’s possible to buy extra rations. They’ll persuade their target to pick up the bill, all the while claiming it’s to feed their baby. The tourist leaves, and minutes later the con artist returns the milk for a refund, splitting the spoils with the shop owner.

Other scams are less developed, however. The taxi drivers who fiddle their meters to charge extortionate fares. And of course, the coin sellers: in particular, the three-peso coin in Cuba’s national currency makes for a popular souvenir, featuring as it does the face of Che Guevara on one side. Several times I was approached by scammers trying to sell it to me for five dollars as a “limited edition print”… a more accurate conversion rate would value it at $0.11, however. Weeks later I’d be chased down a street in Trinidad by a toothless old man, who babbled in Spanish as he desperately waved his Che notes at my back.

Others are simply opportunists, with no real game as such – they want what you’ve got, and they’re not afraid to ask for it. Another time, in a bar in Matanzas, I met a man named Jorge. He was 50 years old, and happened to stop by on his way home from his factory job. He asked if he could join us for a drink (which in Cuba, generally means the foreigner is paying). I bought him a drink, and then he asked for my sunglasses. I gave him my sunglasses, and then he asked for five dollars.

Then there was Cesar. Cesar was a young black student, who approached me during those early days in Havana. He pulled all the usual moves: tried offering me cigars, weed, cocaine, vintage rum, and so on. I kept telling him I had no money, and he clearly didn’t believe me. A white foreigner, in Cuba, with no money? Obviously I was lying and he just hadn’t hit the right buttons yet. Cesar followed me for most of the afternoon as I wandered through town, and even waited outside when I tried changing up Russian money in a bank (to no avail). Eventually he invited me to go for a drink with him.

Much like the milk scam above, there’s a common trick which involves a local taking you out for a drink at their friend’s bar. You’ll pay for everything, and the bill will be far too much. As soon as you leave your host will head back inside, where the bar manager will offer them a “finder’s fee” for delivering yet another rich and gullible tourist to the slaughter.

I could see where this was leading, and I kept insisting to Cesar that I had nothing… then, eventually, something clicked. It took perhaps two hours for realisation to dawn on him, but once he finally got his head around the notion of a penniless tourist in a bad situation, he dropped the games immediately. We went out for a few cocktails together after all, and Cesar paid the bill. During that time we chatted about life in Cuba, he showed me pictures of his family, and even invited me to come for dinner at his house one night. (Naturally, I accepted… but that’s a whole different story.)

In time, this would become a typical experience. It’s true that the vast majority of Cubans seem to want to talk to you, and yes, many of those will try to take your money. There’s no getting away from the fact that most visitors to the country have access to wealth beyond the wildest imaginings of the locals. Life can be tough here, and it’s only natural that they’re going to want to learn English, and work out peaceful (albeit usually dishonest) ways of getting you to share your riches. But when you strip that privilege away, if you can manage to convince a Cuban that – contrary to everything they’ve been taught – you really do have nothing to give them, in my experience, the majority will still want to be your friend anyway. These people are hungry and very often desperate, but beneath it all the Cuban spirit is warm, generous and companionable.

By the time my friends eventually arrived in Havana I was able to borrow money, make online transfers, and repay my hosts beyond their expectations. When I donated an old mobile phone to my surrogate mother as a gesture of gratitude, she broke down into tears and began smothering me in hugs and kisses.

What had initially looked like a disaster turned into one of my most valuable travel experiences to date; those first four days in Havana gave me an intense crash course in speaking Spanish, but more than that, they offered a priceless insight into day-to-day Cuban life.

The experience also showed me the nature of true Cuban hospitality, which was something I would remember later; as the weeks went on and I was exposed to scam after scam after scam. While some of the other foreigners around me experienced predominantly negative interactions, I always had that initial experience to refer to, and I never forgot the deep generosity which – in spite of the games, the corruption, the trickery which plagues the Cuban tourist trail – nevertheless lies at the heart of Cuba’s national character.