Exploring Cuba by bike

by Wade Trevean

To outsiders, Cuba represents something of an enigma; a country seemingly frozen in time, despite recent advances, and one that promises much to the intrepid traveller. Armed with a single-speed bike, minimal gear, a healthy curiosity and several weeks of freedom, Wade Trevean ventured to Cuba to learn more about the island nation and what it has to offer cyclists.

“It is by riding a bicycle that you learn the contours of a country best, since you have to sweat up the hills and coast down them.”

– Ernest Hemingway (Occasional resident of Cuba)

Soon after getting married my wife and I made plans to visit Central America for our honeymoon. And then she threw in a curve-ball — she would let me head over a month earlier and we would meet each other there.

Having never travelled through the Americas my mind ran wild. Should it be a trek through the jungles of Colombia, a trip to the capital of Venezuela – simply so I could say I’d been to Caracas – or a ride around the slightly mysterious Cuba? I chose the last of those options, my intention being to use the bike to help learn more about this enigmatic country (all while getting in some winter training).

With my destination sorted and plans made to meet my wife in Guatemala City a month later, a Michelin map soon became my chief source of distraction. My previous cycling trips included an unsupported 11,500km jaunt through Africa with four mates but on this trip I would take a more minimalistic approach. I had far less time (approximately two weeks) and I assumed the conditions would be far more manageable than riding through the Sahara.

This agenda encouraged me to leave my Surly Long Haul Trucker, tent and satellite phone behind and instead aim for a simple (and cheaper) bike that I could leave behind once finished, a daypack and just my own thoughts. A friend’s commuter fit the bill: a correctly-sized road frame, decent set of wheels and, most importantly, it looked good. The only modifications I made prior to departure were a back rack, a fixed hub (adding to the simplicity), SPD pedals and a donated saddle thanks to friends at Busyman.

My intended route avoided the main roads, included towns that, I hoped, had some sort of accommodation, and gave me the opportunity to see several key sites. Overall I was aiming for an average of 120km per day for a total of roughly 1000km for the trip. Having recently spent a day doing a 500km solo ride around my home state of Victoria I assumed this was manageable.


After landing in the capital Havana with a bike that got lost twice in transit, my trip was eventually underway. I was soon sitting on an overnight bus heading east to Santiago de Cuba with minimal luggage and my still-boxed bike underneath. A few spare hours in the capital and the partial insight provided by a copy of ‘Our man in Havana’ was enough to inspire a return visit. Havana seemed to be a place that offered inviting residential streets to explore and many untold stories.

I spent a day in Santiago de Cuba playing tourist, losing to locals at chess and setting up my bike in anticipation of what lay ahead. The goal of the trip was simplicity and my belongings suggested as much. My daypack contained just one change of clothes, basic tools (multi-tool and pump), some tubes, a small camera and a mandatory occy strap (tie down). I was using the back rack to avoid having a bag on my back and the only other thing on the bike was a single bidon. I left my GPS unit at home.

Ignorance is bliss. Leaving the comforts of the country’s second biggest city behind I started my indirect route back to the capital, the first two days of which saw me hug the coast towards Manzanillo. Occasionally I’d pass small riverside villages, hidden in valleys away from the road. These towns consisted of a mix of formal concrete housing and wooden huts.

I had spectacular views of the Caribbean Sea to my left and, to my right, the country’s highest peaks, tumbling down through the valleys, defining the curvature of the road. The heat and accompanying sweat made the water an inviting prospect; my traditional mindset of aiming for my day’s destination in good time was often replaced with a random swim. The joys of a flexible schedule.


Whilst the picturesque view didn’t change much during the initial days the paved road soon disintegrated and then simply ceased to be. With the road’s proximity to the ocean a 2005 Hurricane had certainly left its mark. Tunnels had been disabled and roads had simply been washed away. For me this meant walking at times and several punctures.

The first puncture made me curse at having forgotten to replace the worn 23mm Continental tyres with something wider and more durable. I had no faith (as was later vindicated) in the self-adhesive patches I had bought, despite the bike shop’s assurance of this particular brand. It was later that day as I was led down a dark path into a chicken shed that practical experience cured my frustration.

A local ‘poncherro’ perfectly demonstrated the Cubans’ approach to making the most of what you have. They showed me an alternative way to fix a tube when you don’t have the luxury of a 10 pack of tubes delivered to your door quicker then you can throw out the ‘old’ one. An old tyre was cut and used as a patch, a vice used to aid its fixing, before the patch was heated up to properly melt onto the damaged tyre.


The first night’s accommodation was an introduction to the varied options that were to come. In this instance I occupied a room at a school camp; one that seemed to be at near full occupancy. I opted for a single room — complete with ants’ nest — to avoid the all-night shenanigans of my co-tenants.

Having left my tent and accessories at home I needed to aim for shelter each night, which in most instances was a ‘Casa’, a local’s house with a spare room. In line with communist ideals, private businesses don’t tend to be encouraged so this type of lodging was commonplace in most towns. This was a win for me — I got to enjoy home-cooked meals, have my one change of cycling clothes washed and to engage with the locals, learning about Cuba in the process.

Sitting down for breakfast at these houses I got to enjoy a variety of fruits, eggs, rolls etc… It was only when I visited the stores and noticed the bare shelves and limited goods that I realised the home owner needed to have visited several stores at a very early hour to provide me with this meal.

My fuel (food) on this trip was predominantly two or three servings of rice and beans, some ‘traditional’ Cuban pizza for carbs and an occasional energy fix thanks to state-run ice-creameries. Fruit was certainly in abundance and something I took advantage of when available, whether it be sharing a stick of sugarcane with a local farmer, sharing mangos in a police station or a handful of bananas from another local after being offered a whole bunch.

As for the necessary liquid in the warm conditions, I aimed to avoid continually buying bottled water. Instead I successfully quenched my thirst by calling on the kindness of strangers, knocking on their doors to ask in my very basic Spanish if I could get my bidon filled up, coupled with a dramatised look of thirst.


From the seaside resort town of Marea del Portillo I moved on to to a night’s rest in the sleepy town of Manzanillo. From there it was on to Bayamo, the provincial capital, at which point the rock-strewn roads were behind me, having been replaced by now-continual bitumen.

The bike was performing well, reinforcing my choice to bring one from home rather than buying one on arrival. This was further reiterated when noticing that most ‘new’ bikes featured the early 1990s rage of 27-gears, including those of the police, while local bike shops only offered very basic spares. Although I had a free-wheel hub on one side I never swapped from the fixed gear (48×16). There were no alps to conquer yet the route inevitably took in some climbs where I definitely reached for that elusive extra gear.

From the east of the country my route followed a predominantly western trajectory, slightly dictated by the direction of the wind. I always aimed for B-roads despite the fact the main highway (which I crossed over twice) teased me with a direct route to Havana.


The scenery of everyday life offered people fishing from bridges, farmers armed with sickles slashing at their fields and informal games of baseball where I was hoping for an invite. It was these roads that allowed the engagement with the hidden Cuba, small towns, places which seemingly hadn’t changed much in recent decades.

During a visit to one such town I followed the faint sound of drums to an abandoned warehouse where I listened to a ‘Son’ music rehearsal. In another I got stopped by locals for a few cheeky shots of rum from a mysterious plastic bottle while others centred around their once economy-defining sugar mills.

Outside the towns I was afforded the simple joy of just me, my bike and the road, allowing cleansing thoughts and the opportunity to appreciate the surrounding environment. The only hassle: having to avoid the occasional donkey-led cart. The silence of the rural areas was only interrupted as I swapped greetings with local farmers, allowing snippets of engagement as I was assured of my directions.

Throughout the country a common reaction when explaining to locals where I had ridden from and my end destination was the international symbol of ‘crazy’, shown by a circling finger near the temple. My Spanish vocabulary was increasing!


My days of riding in the middle of the country were shorter, allowing stops and the chance to appreciate the spaces between them, long lunches and early arrivals to further discover at my destinations. Over the course of several days I rode through the Che Guevara-dominated town of Santa Clara, enjoyed the UNESCO town of Trinidad famed for its cobbled streets and coloured colonial houses, and spent time in Cienfuegos, a bayside town with an neoclassical architectural style indicating its important role in Cuba’s identity.

I quickly eased into the simple routine of beginning my day’s riding as the sun was rising in an attempt to avoid the heat of the day and to allow glimpses of communities starting their day. I’d often ride with locals until our paths deviated — theirs to work whilst I continued onwards, aiming for a new town.

The landscape was lush, highlighted by a spectrum of greens with the occasional cleared field, while the road was smooth with occasional ascents to offer elevated glimpses of what lay ahead. Upon entering my daily destinations I aimed for the ever-present town squares, finding accommodation close by where I could.

The more developed towns allowed opportunities to ignore my failings in Spanish and partake in English conversations with some of my hosts, offering further insight into present-day Cuba. Many tourists spoke of their hope that, despite the ongoing political changes, Cuba would remain the same, offering them a glass-bubble-glimpse of a vastly different life.

Yet it was the locals who hoped for change and the opportunities that, they thought, democracy would bring: a chance to try one of those western hamburgers, trust in their neighbour or the chance for a doctor to earn more than $42 per month.


I wanted to reach Havana a day earlier to allow myself enough time to explore the city. I reluctantly squeezed two planned days of riding into one, learning that 180km on a fixed-gear bike in warm conditions is pretty hard.

Setting off from Cienfuegos my aim was Matanzas (the ‘Athens of Cuba’) with the thought that, if I didn’t make it that far, it was OK due to a the number of smaller, accommodating towns in between. Despite the sweat-inducing heat, the wind and some other excuses I came up with along the way, it was inevitable that I was going to push myself for that extra day.

Fortunately I was inspired by the encouraging revolutionary slogans on billboards lining the roadside featuring the likes of Fidel Castro, Hugo Chavez and Vladimir Lenin. As I inched closer to the capital on these slightly busier roads, I had the chance to partially judge the locals without actually meeting them. In Cuba’s case this showed them to be a considerable bunch, often nearly driving off the opposing side of the road as they drove past me, an exaggerated gesture of kindness.

This provision of safe passing distance also minimised the amount of exhaust fumes I breathed in from the plethora of old American classic cars passing me by. And not the ones you see in those glossy ads.


My final day on the road was spent hugging the northern coast with road signs constantly counting down the kilometers to Havana. The easy ride allowed reflection on my fortune of having had this experience, smiling to myself as I rode.

Closer to the city directions became misleading. I found myself covering an extra 20km I wasn’t banking on, all the while dealing with traffic I had been able to forget about for the rest of the trip. I was pretty happy to be finally dodging the tourists on the cobbled streets of La Habana Vieja, the old town, where I would find my hotel and a fresh set of clothes.

In Havana, playing tourist, I had to adjust to the chaos of the capital having spent the last two weeks in more relaxed settings and mindset. It was only after a day that I grew restless and yearned to discover more, to simply keep riding further to the opposing edge of the country and then some. But after a couple of rides through the capital I stuck to my intent (and promise to my wife to greet her in Guatemala sans bike) and found a worthy donor for my trusted steed. I left the bike with Luis Miguel, a young local who was keen for some transport.


Cycling through countries (or continents) offers so much more than the car. The slow pace really does open a clearer understanding of a country; it makes you more receptive to the subtle changes, whether it’s the visible transformation of the landscape, differing cultures between regions to the opinions of the locals. The achievement (and hardship) of knowing that the only way of getting from A to B is your legs and mind is simply joyous.

Experiencing new roads heightens this to a level that reminds you why your bike is your preferred choice of transport, whether on newly discovered back roads in your local neighbourhood or the rock-strewn roads of Cuba. It’s the experience of difference.

I can definitely recommend Cuba as a cycling destination. Despite seeing no other cycling tourists on my travels it was incredibly safe and everyone was certainly accommodating and only too happy to offer their generosity.

Cuba has a wealth of experiences on offer, whether it’s the varied landscape that one can witness on its quieter roads, the locals, or the ability to learn its history through the places visited. Although not the largest country it offers enough back roads for the sense of discovery, the joy that comes from small, less-visited towns with accommodation and mandatory rice, and that shared international sign of crazy from the warm locals.

Click through for maps showing the first part and second part of Wade’s journey across Cuba. Click here to see more of his photos. Hi-res versions are available for sale, with part of the proceeds going to charity.

You can also follow Wade’s adventures at his Instagram account.

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