Backstory: Hitchhiking my way around Cuba

Finally, I decided to give up and take a collective taxi going to Sancti Spiritus. The price, announced the driver's assistant, was 5 pesos (18 cents), to be collected by assistant No. 2. Half the people at the hitchhiking stop paid up and piled into the '56 Chevrolet. "Not to worry," the policeman assured me as I waved goodbye. His free ride would eventually come. "The system is slow," he said. "But it works."

Fernando, the Chevy's driver, was really a rowing instructor who earned a state salary of 500 pesos ($19) a month. But he inherited a '54 Buick several years ago, which he fixed up and traded for the Chevy. He filled out the paperwork and, a year later, got approval to switch jobs and become a driver – and now makes four times what he did as an instructor.

Such permission, of course, comes with regulations. He can, for example, only make one run on his two-hour route a day. "Why?" I ask. "That's just the rule," he said, bemused at the question and slowing down for the second police inspection in half an hour.

On Day 2, I didn't hitchhike either. I wanted to. But it was not to be. I was told the Sancti Spíritus-Caibarién road, where I was going, was a bus route, which meant no amarillos, few hitchers, and even fewer people moved by the spirit of socialism. There was only one other problem – the bus was only for Cubans. I could have taken the tourist bus – at nine times the price – but it had just left, according to station master Fidelito. But not to worry: Fidelito's friend, Juan, who runs a small unofficial transport business, was going to help.

Soon enough, Juan and I were road-tripping along in his rebuilt Russian Lada. He would be fined if caught with a foreigner, so he asked me to pretend I was a mute cousin. Later, we made a detour to see a monument to Camilo Cienfuegos, a hero of the revolution, in Yaguajay. It was impressive, but we had to whiz by to avoid police. I stared out the window at coconut trees and billboards. "Life is worth living," read one. "Plant ideas and they will grow," suggested another.

I was getting discouraged with hitchhiking, when, on Day 3, it all came together. As I stood outside Remedios, an amarillo finally stopped a state vehicle, a minivan filled with workers returning from a "fun day" at the beach. I jumped in. We then pulled over for the driver to buy some avocados. We stopped later for onions for the driver's assistant. We picked up a family going to see cousins. No one talked to me, but it felt great. I was hitchhiking.

I got dropped off in Santa Clara, where I went to the Che Guevara museum. And then, still humming the catchy revolutionary tunes piped in over the speakers there, I got another ride. And another – all the way back to Havana. My fortunes had turned.

There was Pablo with his horse and buggy, who wedged my laptop bag between his legs and the horse's backside for "safekeeping." Caesar and Diego from the national water department, who told me about their time as soldiers in Angola. And Luis Alfonso, a cancer specialist, who took me for tea at his great aunt's home. By the time I rolled into Havana the next evening, chatting baseball with my new friend Jamie from the Finance Ministry, I was a bona fide hitchhiker – living the Cuban experience.

I was also ready to hail a tourist cab.

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