Imagine a place that is both the past and the future, both heaven and hell. A place of crumbling splendour and jewelled seas, of derelict buildings emblazoned with the revolutionary flag.

Cuba is the strangest country I’ve ever - and probably will ever - visit. I arrived there on the tail end of a Central American trip, alone, with very little money and speaking barely a scrap of Spanish. I was considerably unprepared for what would follow. Cuba picked me up and it shook me out. Any road-wariness I’d gathered in my travels was stripped away as soon as I landed on the tarmac of that strange, strange place.

Hedonism and poverty, paradise and ruin. Cuba is a strange jumble of contradictions.

The Cuba that exists today is the culmination of so many eras. It is impossible to describe my experience of this place as something not affected by its multifaceted history. Believe it or not, for the most part of the 19th Century, Cuba was actually incredibly rich. As a Spanish colony, it dominated as the world’s leading sugar cane producer and it was this era of prosperity that paved the streets of Havana with opulent colonial buildings. 

But from 1959 onwards, Cuba was a communist state and America, itself in the midst of The Cold War, quickly cut off all trade and relations. Cuba did not fare well in this political isolation and by the 90s things were bad. Marketed by the regime as the ‘Periodo Especial’ (special period), from 1990 to 1994 a crackdown on rationing and fuel meant that widespread hunger was so extreme, it was not uncommon to see a Cuban family rearing livestock in their bathroom just to stay alive.

The view from my apartment in Cuba. To the right is the Cuban revolutionary flag which is painted everywhere.

Tourism is what is dragging Cuba back from its political and economic apocalypse. Today, despite years of inaccessibility, tourism is the country’s biggest industry. Early this year, Obama finally thawed US-Cuba relations allowing Americans to freely visit Cuba for the first time in over 50 years. This will no doubt change things massively. 

But for now, Cuba is still a place of extremities. Extreme poverty contrasted with the comparative hedonism of tourists; five star hotels next to one bedroom family homes. Extreme ideologies are coloured by extreme hardship and disillusionment. And you can tell, you can feel it with every eye on you. These people have suffered and we, the tourists, are both their salvation and their undoing. 


Havana is like some kind of dystopian Paris. Magnificent buildings lie in disrepair, fighting off a new kind of colonisation - plant life. People hang from ornate balconies, yelling at each other in Spanish or lowering items onto the street with a bucket and a string. Men sit in gutters selling gigantic cigars, or push carts with mangos and avocados as big as my head for 20 cents. Shop shelves are almost bare, locals line up on street corners for bread rations and families sell espressos out of their window for one peso.

Everyone, everywhere is scraping by. But it’s not austere. Every Sunday the streets fill with drumming and dancing. Rum, which is cheaper than water (and considerably easier to find) flows everywhere. More than once, I found myself sitting on a stool on the pavement, engaged in an animated game of dominos with a local family while a bottle of rum was passed into my hands.

‘Collectivos' are the Cuban version of a taxi service that feels a little like hitch hiking.

Barely any new cars have been imported into the country for the last 50 years, so Havana is full of rusting, vintage classics. Many of these also serve as ‘Collectivos’; the Cuban transport system that works something like a taxi combined with hitch hiking. I would throw my arm out then squash myself next to two Cuban mammas in the back seat of a 1950s Chevy. Cuban music blasted out of an antique radio and rosary beads swung madly from the revision mirror. You can see all of Havana in these cars. At my destination, I would just yell "aqui!" and thrust 10 pesos into the driver’s hand. And that’s it, a vintage chauffeur service anywhere in the city for the equivalent of 40 cents - that wouldn’t get me 10 meters in Sydney.

There are some badass cars in Cuba.

There are no hostels in Cuba, and expensive hotels are out of the question. For the struggling backpacker like myself, the best and most popular option was to find a ‘Casa Particular’ - a local family who were legally allowed to rent out their spare rooms to foreign travellers. 

My home in Havana was the Hamel House. Run by a local Cuban couple, Magnolia and Wilfredo, they spent their days watching Cuban soap operas, cooking gigantic meals for me and dishing out comforting hugs. Wilfredo was about 100 years old and managed bookings with a piece of grid paper and a pencil – not a computer in sight. Magnolia’s Cuban accent was so thick that I could barely communicate with her. But my charade skills are on point and considering our frequent hugs I think she liked me quite a bit.

Magnolia and Wilfred, my adoptive Cuban parents.

If you don’t mind cramming yourself onto a crowded bus for 45 minutes, two pesos will get you to the Playas De Este, the jewelled seas of Havana’s east. This is where the split in the Cuban economy feels most prominent. Gutted out mansions are scattered like carcasses along the coastline. They stand as haunting monuments of prosperity either lost or abandoned in the tough times of the Periodo Especial. Now they serve as drinking haunts for locals, the twisted cement is as fine a beach umbrella as any.

100 meters down the beach, it was a different scene. A tourist resort pumped out dance music while fat foreigners drank piña coladas and had massages on the sand.

Twisted cement is as fine a beach umbrella as any.

Sitting alone on the sand, I was approached by a big Cuban policeman in aviator glasses. After a broken English/Spanish exchange and a lot of sign language, I managed to communicate that I was walking to the local town, Guarabo, for lunch. He immediately declared that he would accompany me. I was faced with several moments like this in Cuba, moments when I had to decide if I was being adventurous or just plain stupid. A police uniform doesn’t necessarily represent safety or trustworthiness, just as agreeing to ‘lunch’ could be interpreted as enthusiasm for any matter of activities.

Policemen stand guard in a gutted out building on the Playas De Este.

Unfortunately, I’ll agree to almost anything when I’m hungry. Suddenly I was marching down the beach with my own personal police escort, straight through the small village and into the backyard of a tiny restaurant. The term ‘restaurant’ is used loosely here – the backyard consisted of two broken chairs. A bowl of food was thrust into my hand and I started on a very strange, chicken lunch with the chief policeman of Guarabo.

Of course, I ended up having to carefully hedge an invitation to see his house, then tailed it out of there before the situation got any weirder than it already was. Havana is like this, confusing and questionable acts of kindness are as common as catcalls thrown at you in the street. It seems far from ready for the influx of the tourists at its gates.


A five hour bus ride east of Havana is the colonial town of Trinidad. If I thought Havana was a logistical challenge, then navigating my way around this small village was to be my strangest experience yet. Once again, I was alone and, once again, I really couldn’t communicate with or understand anybody. 

Cursing the many hours I’d spent comatose in Spanish class, I wandered the town eating ‘tostada’ and soaking up the live music that was everywhere. All around me, local Cubans danced salsa on the cobblestone streets.

Playas De Este, an eerily derelict paradise.

Mountains fringe the outskirts of Trinidad and rumour had it there was a beautiful waterfall that could be reached only by horseback. I can actually ride a horse fairly well, but a Cuban horse? That’s another story. My horse in particular was underfed and, of course, Spanish speaking. I had to make him move by yelling "cabelllooooooo" (the Spanish word for horse) about a hundred times.

I eventually got him up that mountain and to a beautiful cave-side lagoon of sparkling clear water. However, I couldn’t have been there for more than ten minutes when the local guide I’d hired came running down the path towards me. 

"Vamos, vamos!" He urged me back onto my horse as a huge storm began to build in the sky above us. As we reached the road, rain started to bucket down and the sky lit up with bright fissures of lightning. I was drenched within seconds. Mildly dissatisfied with the trip, I pointed my horse towards town and began the damp trudge home.

Soaking on a horse. I had no idea what I was in for.

My guide however, had other plans. We veered down a dirt track and suddenly I was standing in front of ten Cubans outside their tiny, farmhouse home. There were mothers, grandfathers, uncles, aunts, sisters, and cousins. I had inadvertently walked into a local, private party. I stood there in utter confusion while my guide, who was obviously a family friend, sat down, poured himself a shot of rum and looked right at home. The rain still beat down heavily on the tin roof as I weighed up my options… I really didn’t have any. The storm was at its worst and my horse had already disappeared into the neighbouring paddock. So I took up a chair, accepted the first of many rums and launched into a poorly executed, Spanglish conversation.

The grandfather of the group was called Rafael. He tried to explain to me why they were celebrating and, as I obviously didn’t understand him, he led me into the house instead. A man lay flat on his back on the singular bed. He was completely still, he didn’t move a muscle. I stared at him. He looked dead. He was fucking dead. I stumbled back out of the hut in alarm, trying to remember the Spanish word for ‘deceased’ and thinking that I’d walked into some kind of Cuban funeral party.

“Muerto?” I eventually managed to ask to Rafael. “Oh no, no! Ebrio!” The man on the bed was drunk, stone cold drunk. They were all there to celebrate his 53rd birthday and he’d passed out by 5pm. They cackled at my confusion, poured me another shot of rum then served a gigantic pig for dinner from a pot that had been cooking in the garden the entire time.

Over the next two hours, as the rain beat on incessantly, I ate and drank with that wonderful family, establishing what can only be described as a warm friendship - despite the cultural gulf between us. I felt the most at home since arriving in that strange, isolating country. This was the Cuba I’d been looking for.

Spot the foreigner. Drinking rum with my new friends. To my left is Rafael.

As I left, I promised to learn more Spanish and to come back for a proper conversation. Maybe some day I will. Back on the soaking wet horses, we started home in the fading light. The water was coming down like a river now and I ran that that horse all the way through the village as the cobblestone streets began to flood. I couldn’t have looked more conspicuous; white skin, blonde hair, absolutely filthy and soaked to the bone. People literally hung off their balconies to stare at me. I didn’t care though, I was wearing a grin as wide as my sombrero.


Cuba was strange, at times lonely and, almost always, utterly bewildering. As a budget backpacker, I fell into the gap between five star tourism and local living, and that kind of travel market is only just starting to exist.

I spent a lot of the time trying to be adventurous and not admitting to myself that I was just stranded, sweaty and confused. But that is why I loved it. For every ornate terrace there was a crumbling ruin, for every catcall in the street there was a favour from a stranger. Everywhere I went, I saw the contrast between the Cuba that was packaged and presented to the foreigner, and the reality of a country that has been surviving without us for centuries. A place that is raw, passionate, disillusioned, stricken and proud. I barely scratched the surface of that kind of Cuba, but how long will it even remain?

There is a change coming as Cuba’s doors open to the commercial west. It’s in the boy who taught himself perfect English from Youtube, or the old man who whispered “Viva America!” at me from a park bench. Tourism is giving Cuba a second chance at prosperity, and I can’t lament a change like that. I can only hope it doesn’t dilute the true experience of a place that is unlike anything I have ever seen.

How much will Cuba change? How much do we want it to?