When my mum waved farewell to her youngest son at Heathrow Airport in 2009, as he set off to Havana for a five-week cycling trip with three friends, I am sure the usual worries went through her mind.

I could see them ticking in front of her eyes like updates to a departure board. Questions like: “What if he gets arrested?” “What if he gets a bone-crushing illness?” “What if he ends up sleeping by the roadside?” “What if their bikes melt in the heat?”

The worries manifested as a hug, and off I went. Neither of us knew that all of these worst case scenarios would come to fruition.

It was the kind of ill-advised, dreadfully planned trip you could only get away with in those indestructible twilight years between youth and adulthood. I was nineteen, and had barely ridden a bicycle further than my local corner shop. Yet when my friend, Jamie, suggested a five-week adventure across Cuba on two wheels with two other chums, I couldn’t say no. 

‘From Havana to Santiago de Cuba’. It had a nice ring to it, and being a first-year university student I was near enough a fully fledged communist so Cuba had a particular appeal. So I went out and bought the cheapest hybrid bike I could find and a return ticket to Cuba. What could possibly go wrong?

On our first day, with mojito-and-cigar fuelled hangovers, the four of us navigated the manic streets of Havana to find a country road which promised to take us broadly eastwards. The sun pounded on our bare backs at 35 degrees, turning the water bottles strapped to our bikes kettle hot. But even with that heat, progress seemed remarkably slow. By lunchtime, hours into the cycle, we were close to total exhaustion and had somehow only travelled 20-odd miles. While my friends rested on the cold canteen floor, I opened my Cycling Cuba guidebook to find the piece of advice on the very first page:

“Do not attempt to cycle across Cuba from the west to the east. The prevailing headwind will make it a misery.” 

If your Cuban geography is not up to scratch: Havana is in the far west of the island and Santiago de Cuba in the far east. In having failed to prepare a jot, our mission was doomed from the start. Yet, rather than returning to Havana and redrawing our itinerary, in our post adolescent arrogance we decided a more appropriate course of action would be to shrug our shoulders and carry on.

The wind wasn’t the only thing stopping us in our tracks. Our (first) police scrape came the following day. Approaching a T junction, on a road as dusty and deserted as the American Midwest, we turned right only to be whistled down by a police officer who, by all accounts, had been hiding in a bush. He looked very serious and informed us of our crime, pulling out an official looking slip to issue our punishment. The only problem, for the officer at least, was we did not speak sufficient Spanish to comprehend our felony, and he spoke no English whatsoever.

“I think maybe he’s saying we were supposed to have stopped at the junction?” One of us said. 

“No I think he’s saying we should have indicated to turn right?”

“But the road’s empty, for fluff’s sake.” I paraphrase.

“Shall we just…” Our eyes turned to our bikes, and with a “lo siento” we picked up our vehicles and pedalled fast into the distance with the fist-wagging, whistle-blowing officer left in our wake. 

The officer did not resemble a witch doctor. But if he was, he may have wished some kind of debilitating sickness to have befallen these unruly British youths. And the medium for his curse, perhaps, would have been a delicious roadside pork bap. Whether black magic was involved or not, the illness knocked us out for an entire week and was later diagnosed as salmonella. In two double beds in an un-air-conditioned home in Cienfuegos, we spent our days massaging each other’s gnawing muscle aches and praying for the sickness to go away, while the poor casa owners fed us plain food and offered to help however they could. I remember writing home with a postcard along the lines of “everything is going wonderfully.”

Eventually, the sickness subsided, though the headwind did not, and we got as far as the colonial town of Trinidad (about a third of the way across the island) before we accepted defeat and boarded a bus to the south east, where we would explore the Santiago province. Our woes, it transpired, were determined to follow us.