Cuba: Pirates of the Caribbean

Even before we had arrived we knew that Cuba was going to be a complicated country to visit.

We read about the lack English speakers, the two different currencies (Cuban peso & Cuban convertible peso), the strict rules around time of day that you could buy alcohol, the difficulty tourists had with buying basic groceries and the fact that our ‘global travel insurance’ didn’t cover us in Cuba (but you could be fined travelling in Cuba without any insurance).

To start things off on the right foot, I realised passing through security at José Martí International Airport (nearest Havana) that I had left my phone on the plane. After communicating the issue with staff (and trying to convince my brother that I hadn’t consistently been this useless during the last 7 months travelling), we were told to continue through immigration and collect it at an office in the main terminal. We had only just passed through security and collected our bags before being stopped again by two female security officers. The uniform of very short skirts and very high heels puts Heathrows’ to shame, and reminded us through the frustration of having our bags all checked AGAIN that we were about to arrive in one of the most charismatic cities on earth.

Even after that ordeal, we still had complications finding the office with my phone, and finally spent an age using every credit/debit/travel card we owned until one of them finally processed and gave us money for a taxi. We left the airport tired, on edge and thoroughly sober after celebratory airplane drinks.

The moment you leave the airport you are hit by two things. Firstly; the oppressive humid heat. Secondly; the American vintage cars that Cuba is famous for isn’t just a gimmick that they roll out for tourists – they are everywhere. They range from barely road legal rust buckets, to highly polished labours of love – and are used as everything from family cars, to taxis, to delivery vans. The frustrations of the airport faded as we sat silently in our taxi and cruised past huge ex-colonial government buildings, giant murals of Che Guevara & Fidel Castro, and finally into the tight streets old town.

‘Old Havana’ is effectively the downtown district. It has the highest population density in the city and contains the original city walls, which are now the modern boundaries of Old Havana. It was originally founded by the Spanish in 1519 in the natural harbour of the Bay of Havana and throughout its history has seen gold-laden Spanish Galleons on their way from the New World as well as French Pirates who almost burned the place to the ground in 1555. The history isn’t forgotten, it’s present everywhere you look. Everything you picture as being stereotypical of Havana is there – so much so that it’s almost cartoonish. Our rented flat had a balcony on the second floor that looked down onto one of the crumbling tight streets of the of the old town, and at any point of day you could see withered old ladies smoking cigars as big as my forearm, groups of men sitting in the street playing cards and drinking rum, or kids running after each other barefoot. All this combined with the constant soundtrack of live music meant that the whole place was dripping with character.  

We spent the next few days exploring the cracked streets and colonial houses turned museums. Each historic square was surrounded by niche cafes serving fresh sea food and coffee, and most bars had seating out on the streets to better watch the buskers from. When the heat of the day became too much, we would retreat back to our flat and sip on rum until it was cool enough to venture out again for dinner, or to sit on the sea wall and watch the sunset colours wash over the coastal hotels.

Every local we spoke to were nothing short of welcoming, fun & polite. They were quick to praise their home country – with one man who sourced our cigars telling us that he’s proud that Fidel gave them free healthcare, free education and incredible rum. The latter is a point we couldn’t argue with. The country has its economic problems, but all the basic needs of its people are provided. It’s also a generally a safe country with almost no violent crimes, organized gang culture, teenage delinquency, drugs or dangerous zones. There is supposedly a strict policing known as the Committee for the Defence of the Revolution (CDR) that keep the streets safe from violent crime, although we never saw them out. The safe streets, happy people and every-day festival vibe makes you think if communism is the bad guy it’s made out to be in The West. Having said that, we only really scratched the surface. I’ll be interested to see how this all holds together with the coming tidal wave of tourism.

From Havana, we hopped on a coach and drove west to the sleepy town of Viñales. Set in the base of Viñales Valley, its main street is lined with colourful colonial-era wooden houses and the fertile land around is farmed for coffee beans and tobacco. It’s an odd place to describe; it has the layout of an American suburb, with bright squat houses set back against large fenced off front gardens, their occupants sitting relaxing on the porches. But it had a much more rural feel, with tractors towing trailers of crop down the streets. Part of the reason the area is so successfully farmed is that it’s frequented by sudden downpours due to the hot air rising around the valley walls around it. We were happily sat under a balcony of our villa during a storm that developed and fell in less than a few minutes. We laughed and watched the torrential rain fall until lightning stuck the building across for us and we dove for cover. No sooner had the apocalypse come, it disappeared leaving only refreshingly cool air in its wake.   

As is much of the way with Cuba, any local can sort out anything for you. As we were walking past a restaurant, we were invited to enter by a waiter. After declining, we struck up conversation about our plans in Viñales, and the fact we wanted to organise a horseback tour of the surrounding landscape. He called a friend and had it booked for us in about 10 minutes.

We were picked up by a couple of genuine Cuban cowboys the next day and taken in horse and cart to a small ranch. We were then each given a horse and told not to worry too much about the technicalities of how to ride them, as they were ‘caballos automáticos’ – automatic horses who knew where they were going, we just had hold on.

We all plodded along the valley to a coffee plantation where we were shown the plants, the beans themselves and the processes they use to produce the coffee.  Next stop was about rum education – complete with samples of not just the rum, but the locally produced honey & sugar cane juice. This eventually led to rum cocktails and fairly unsteady remounts onto our horses. We continued through the beautiful landscape, across fields and up rivers, until we reached the tobacco fields. We met a gentleman who explained about the tobacco, the cigar industry as a whole, the process of hand rolling & the etiquette of cigars. As we smoked our sample cigars our cowboy tour guide handed out more rum, and we played with the cigar expert’s kitten. As best jobs in the world go, these guys are pretty high up the list. 

Riding through the Cuban countryside was unforgettable. We’d spread out and ride together across open farmland for a while, then squeeze single-file though a tight ravine. Eventually we started working our way uphill away from the valley floor – with our horses slipping over loose rocks as we climbed, until we reached a wooden shack/bar which looked out across the farmland. Exhausted from the rum and heat, we sat quietly and contemplated the day over the rest of our cigars. The shack served as a perfect final stop on our tour – the stunning views gave us a chance to reflect as we looked down into the valley across the trails through to tobacco fields we had rode along earlier. As we cooled down, the rum came out again. We drank, listened to music and laughed with the locals until it was time to saddle up and head back to the ranch.

The ride back was a much less relaxing experience. Laughing and joking with our cowboy guide has built a rum-fuelled excitement which seemed to have spread to our horses. (Either that or the horses knew that the journey was almost over and were keen to get back to the ranch.) We set off at a much faster pace, which was then spurred on by our guide. We clung on all the way back to the ranch where we bid ¡Adiós! to our Cuban cowboy and wobbled back into town towards our villa.

After a couple more tranquil days in Viñales, we headed back to the perpetual party of Havana. Our last few days consisted of drinking Daiquirís at the bar where they were invented, struggling to find open restaurants due to city wide power outages, and having run out of coconuts on the beach.

Cuba was distinct from everywhere else we’d travelled. It’s beautifully friendly, but only once you pass airport security. It’s very relaxed, but rarely quiet. It’s incredible history and style gives it a feeling of the last pirate stronghold, and its diversity of influences has produced music, food & atmosphere that is now globally celebrated. I worry that Cuba’s newly opened doors will spoil that sense of community that has produced the fun and safety that Cubans enjoy – but who’s to say that adding more influences won’t improve their quality of life. The melting pot seems to have worked well for them so far.


FoodSo much Lobster!Lobster & Rice
DrinkHavana Club. I’ve never enjoyed rum so much in my lifeHavana Club & Pineapple Juice (on the balcony in the old town)
PeopleThe Cuban cowboys Nat, Nicola & Hugh! Who made this trip unforgettable
PlaceOld town, Havana. Just like the movies.Santa María del Mar beach
ExperienceRolling & Smoking Cuban cigars Horse riding in Vinales valley
Culture shockCommunism could be worse… Socialism in 21st Century: the hardest thing of the trip was actually finding a shop to buy food from
Any otherHope it doesn’t change too much!  Happy people, happy place

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