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Memories from my Gap Year: Backpacking around Cuba

On the beach with the Germans           You might have seen from my previous post about the ‘Tales of Two Cities’ travel writing competition run by Black Tomato, and I did actually enter the competition as well because, you know, as travel writing is kind of my thing. The journey I chose to recount is from my month spent backpacking around Cuba after finishing school, aged 18. I’ve written about my trip to Cuba in a couple of other posts (Art: The Malecón in Havana, My Questionnaire for the DTour of a Lifetime and Postcard of the Week: Havana’s Malecón) but never as in-depth as the piece of writing below. It was such a special and unique trip, and I hope this post will give you a flavour of what we experienced during that month!

Santiago de Cuba          Right at the start of my Gap Year before starting university, my best friend and I set off intrepidly to backpack around Cuba for an entire month. We spent the first few days exploring the inimitable Havana and then headed down by a rickety old bus to Trinidad, a small but stunning town on the south coast, adorned with palm trees, charming locals and houses painted in every shade under the sun. One evening, with Mojitos in hand, we sat in the town square enviously watching far more talented dancers than us salsa their way around the square. Earlier that day we had “experienced” a salsa lesson from a Cuban man about whom the very stereotype of the ‘latino lover’ is based, so corny was the sleaze that came out of his mouth, and we’d both agreed that we needed a little more practice before launching ourselves into the public arena and debuting our salsa moves. So there we were, sat commiserating and looking longingly towards the moves the locals were capable of, when two Germans sat down beside us, looking similarly sheepish and incapable of anything as beautiful as salsa as we did.

Trinidad          This mutual feeling of inadequacy mixed with amazement that we four felt formed a sort of bond, and a few hours later, and many many Mojitos later (we were on holiday after all!), we decided to hire a car between the four of us to travel around Cuba, and discover everything Fidel Castro wanted to hide from foreigners. The bus routes for tourists are extremely limited, showing you only the curated towns that will paint Cuba in a good light, and we soon discovered that there was far more to discover out on the open road in our own set of wheels.

Church          We ummed and aahed over whether to hire a bright-red classic 1950s American car, which you still find all over Cuba due to the embargo that’s practically banned all foreign trade. But practicality took over once we heard stories of how often they break down, and we settled for a Soviet-era car instead. And off we set! En route to the country’s second largest city, Santiago de Cuba, in the south-east of Cuba, near Haiti, we passed many smaller towns, some of which were completely free of tourists and where the true effects of the communist dictatorship can be seen, where the citizens depend on rations and are stripped of many of the liberties that we Europeans and North Americans take for granted. In these towns, the government had done nothing to paint a pretty picture and we truly had our eyes opened to the wretched reality. Without a hire car we would have never experienced the true situation, and we’d never have met many of the colourful characters that live in certain parts of the Cuban countryside.

Cayo las Brujas          Another particular occasion for congratulating ourselves on choosing to hire a car came on the return journey towards the north-west, when we discovered the deserted beaches of Cayo Las Brujas on Cuba’s north coast. Sparkling clear waters + bleached-white sand = paradise. Cayo Las Brujas is located on a thin peninsula that juts out into the Old Bahama Channel (the name really says it all doesn’t it!) and is the preserve of one or two high-end luxury hotels that were astronomically outside of our backpacker budget. It’s such an exclusive strip of land that there’s not a single mode of public transport that can take you there, and even local taxi drivers aren’t allowed to drive there. However, with our hire car we could stay the night in a casa particular (the Cuban version of a B&B) in the mainland town of Caibarién, and drive to the Cayo each day to soak up the sun and drink yet more Mojitos, in absolute peace and quiet.

Sandcastle          Having travelled the length of the country and back for 4 weeks, our exploits with the hire car came to an end back in Havana. But if we thought the excitement with Cuban cars had ended there then we were very mistaken.

Havana          Potentially the most eventful car journey of all was in fact a ride in an ancient Cuban police car. First of all, I’d like to clarify that we weren’t being hauled off in handcuffs to jail, they were just giving us a lift from a certain beach (and apparently a haunt for thieves) to the police station to report the theft of some of our belongings. Three policemen, three of us, one 5-seater police car. (The other German wasn’t there at the time). So what do the police do? They put four of us in the back, and luckily it wasn’t exactly difficult to choose who should have the seatbelts, as there weren’t any anyway! So off we zoomed back to Havana in this crowded car (I say zoomed because these keen policemen were definitely speeding and breaking all manner of other laws) and as it happened they ran over a dog on the journey! With us in a rather distressed state of shock and concern for this poor innocent dog, they simply laughed their heads off, swore at the dog and on they drove. It was all rather surreal to be honest and certainly a story that my parents back at home found difficult to believe…

Pineapple on the beach          Our month-long adventure around Cuba via the pot-holed and battered old provincial roads was by far the best way to see this unique country, whose political set-up makes it unlike any other country you’ve been to. The people we met, the coastal views we alone witnessed and the trials and tribulations of navigating with wildly inaccurate road maps truly made the trip for us, and made it a journey I’ll never forget.


Libby and I


  1. Sounds like an incredible trip filled with so many memories! I have never been – and beforehand it hadn’t really been on my radar to visit but you have intrigued me about Cuba now! x


  2. This has made me want to go to Cuba so much! Great post. Thought I’d have a browse on your blog after entering your bestival comp. Now I’ve got the travel bug!! Need to add Cuba to my bucket list now!


  3. Hi.
    Great blog! I’m planning to go to Cuba this year and I heard that you have to have $100 per day of the stay in Cuba when you not travelling with an agency. How much of this is true? Also, were there any problems with getting into the country or did you need any other documents other than your passport and la tarjeta de turista? Thanks


    • Hi there, I had to apply for a tourist visa before we flew to Cuba, but other than that we just arrived. However I have a British passport so it might be different if you’re from another country (I’m guessing so if you use dollars). I certainly didn’t spend $100 per day travelling around Cuba! I visited Cuba for a month and spent maximum £1,250 I think in total, we were backpacking and staying in local casas particulares (B&Bs). However that was almost 8 years ago now, back in 2007, so I imagine prices will have gone up a lot! I’m also worried about the effect an influx of US visitors will have on the country’s tourism, I think it might overload it as it’s not a huge country, and a big increase in tourism will certainly push prices up.


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