Backpacking in Cuba!

Cuba! Well that’s a story from the old days. A journey with a number of near death experiences, a Samsonite in tow, a cigar scam, food expeditions and a small “heavenly” island. In short, a journey that you won’t forget.

With eight friends we wanted to make an adventurous trip to an exotic country. We decided to go to Cuba. Not an all-inclusive trip to tourist resort Varadero, but we went backpacking! I mean seven backpacks and one Samsonite!

Cuba, the country where Fidel Castro was still in power, communication was almost impossible and we had no idea what to expect. An era in which everyone had just got his first mobile phone, and Facebook didn’t exist yet. Booking a trip online or making an online reservation was still in its infancy.

Eventually, booking the flight was not the problem. Finding a location in Havana where we could sleep with eight people proved to be much more difficult. I don’t know how, but we found this vague website where we contacted a Professor. He could offer us an overnight stay in his own house for all of us. We exchanged our names, our flight number and the date of arrival. That seemed sufficient to me and my co-organiser. Once on the plane, not everyone was overly excited about our non-existent “backup” plan (we didn’t have an address, no telephone number, no money yet, nor any alternative and we were about to arrive at midnight). But, on arrival there was this very cute old man, the Professor, waiting for us with a small cardboard sign with one of our names on it.

We slept in a so-called Casa Particular. As a tourist you will spend the night at a Cuban’s home, like a Bed&Breakfast. That was well arranged all over the country. During our trip, we slept at various such special locations. We have met a lot of nice, crazy and talkative Cubans, although the latter was not always easy in our best Spanish, eh oui…..oh eh si!


From Havana, we travelled by train to Pinar del Río. We bought tickets for the night train, a brilliant idea to save money for an overnight stay…..not!  It was such an old train, that stopped everywhere and whistled and stopped and whistled. Once we had somehow fallen asleep, we were summoned to leave the train in the middle of the night somewhere in no man’s land. Due to the smoke, it seemed that the train was on fire, but soon we discovered men with huge spray cans. They were fumigating the train, because we drove into the tobacco region of ​​Cuba.

Pinar del Río

And yes, in the tobacco region we obviously had to visit a tobacco plantation and buy “real” cigars. In a tiny cabin we were sworn by a heavily pregnant woman that these were the real ones. Cohiba, Romeo Y Julieta and Montecristo, these brands were all neatly packed in “original” boxes. The men of our group bought a few boxes. It should come as no surprise that these cigars were not very smokable.

The idea was to celebrate New Year’s Eve with a cigar on the roof of our Casa Particular. A few drinks, watching fireworks and thereafter looking for a bar or some kind of New Year’s Eve party. Not everyone made it until twelve o’clock haha, and at twelve o’clock…..a deafening silence, we didn’t hear a sound, no fireworks, no party, nothing. Happy New Year!

Continuing our journey from rainy Pinar del Río to a small “heavenly” island just below Cuba seemed like an excellent plan. By plane…..a small plane…..a small old plane…..a small old rickety plane. When the propeller engines started to crank, smoke started to spread through the cabin. The stewardess was not able to close the door of the plane at first. How she ultimately managed to do so was not visible because of the smoke.

The small “heavenly” island turned out to be cold and wet. The beach and the water were filthy. And worst of all, this tropical island went without sun during our stay. We couldn’t find any food. In a desolate bar we managed to consume the whole stock of liquor (with the suspicion that something else had been poured into the original bottles). One hundred US dollars lighter and the eight of us were wasted!

Fortunately, back on the mainland, we were able to enjoy the sun, in the Bay of Pigs and in the idyllic town of Trinidad. The taxi trip was wild as usual. I have never sung so loud and long to keep the driver awake. Even the cola drink we bought for him along the road did not stop him from constantly nodding off while driving. We were “lucky”, because this taxi driver didn’t drink rum while driving or drove like a maniac, as we had experienced before.

The Bay of Pigs

It’s quite a miracle, that we have all survived this trip haha.  Including the Samsonite that does not fit in the little Trabant car, cannot roll on non-existing sidewalks and does not fit on your back if you have to hike.

Was it such a dramatic holiday?? No, it was brilliant. I have been on an incredible adventure, with seven very good friends of mine. We’ve laughed, we’ve cried, we were grumpy at times, we joked a lot, we have been getting to know each other even better and we’ve made great memories. To this day we still laugh about it, when we talk about the good old days.

In other words, I would highly recommend visiting Cuba. With a slightly better preparation, and as I assume it’s nowadays more accessible, you will have the holiday of a lifetime!


For this travel blog I have been photographing the physical photos, because I didn’t have digital ones, haha. At the time I thought the photos were exceptionally great. When I look at them now, I see valuable memories, but the quality is hopeless.

Are you planning a trip to Cuba soon? Buy the Lonely Planet, you will definitely need it! Click on this link to buy on the Bookdepository or click on the book below to buy via Amazon.

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