Three countries have been on my list of to-dos since I was a child. The first one was Jamaica. I think Cool Runnings had something to do with that. Investigating it as an adult though, it looks more like a resort island than anything else. Kingston looked good, but all in all unless we could find a remote beach playing Bob Marley with a bunch of chilled out Jamaicans, we didn’t fancy joining a legion of boat cruise passengers as they scrambled for overpriced water activities. I sound averse to cruises. That may or may not be true, depending on whether there’s a cruise out there that suits my philosophy on travel. For example, I’d take a cruise to Antartica, because how else would I get there? I’d take one through Alaska, or any other inhospitable terrain that requires something big to transport me. I don’t like the idea of stopping off in a built up tourist port for a few hours, being denied the chance to really experience the local culture and understand the country, and then being shipped off comfortably to the next destination.
The reason the cruise ship concept is a nightmare for me, is because I imagine myself leaving the blue shoreline and wondering what it is I missed out on. And from our experiences, you find the best surprises by just wandering around. For this reason, cruises to the Greek islands should absolutely be banned. Same with the Danube River. It’s criminal to transport passengers to Eastern Europe or Greece and imply via itinerary, that “what you see is what you get”. It’s like unwrapping a chocolate bar and not tasting it. It’s an unforgivable, overpriced tease. There’s definitely a gap in the cruise market for prolonged stays of even say, 4 days in each place. Just enough time to at least see something genuine. Or a hop on hop off concept. Catch a cruise to Aruba. Hang out for five days. Get on the next cruise to Barbados, then onwards to northern Brazil.
I’ve also wanted to visit Russia since dad bought me a zippo when I was a kid with a gold and red hammer and sickle on it. A symbol of the Russian Revolution. Similar to the red star in where else but…Cuba.
This misdirected rant has a point: The Caribbean, apparently, would never be what I dreamt it to be, unless I got to the West Indies. Well, that never happened, but what did happen was something entirely unforgettable.


We went to Cuba. Possibly the most interesting, culturally-rich and otherworldly place on the planet. And it was in the Caribbean. Win-win.
Havana is hot. You will drip with so much sweat you’ll think you’re walking through a pool all day. The people are generous and gentle. At night, the city streets are pitch black. You will be apprehensive about walking through the shadows as figures dart across the street, ramble on the kerb and seemingly appear out of nowhere. It’s the perfect place to mug somebody. But it never happens. Cubans are a different breed. They’re incredibly helpful and brave a smile through their hardship. It’s easily the safest country we’ve been in on our Latin American adventure.
We arrived at our first casa early in the morning. It must have been 6 am. The streets were dark. The sky was black. People were sitting on the kerb. It didn’t feel at all welcoming. A man got up and started to approach us as we knocked on the door to Mildred’s house. He had been watching us for the last few minutes. We had our bags on us, and we were in a poor country that was communist-cum-socialist. If we got robbed, I could hardly blame them. Whatever it is they wanted, they surely needed more than I did. Saying that, after having my camera and wallet stolen in Brazil, I was down to my last debit card. I had brought a backup with me on this trip in anticipation that I’d be robbed at least once. As fate would have it, it was in Rio – the same city that countless other travellers had told me they had been robbed in.


The man was dressed in a white singlet. He said something in Spanish to us that I didn’t understand. I only knew how to order something at a restaurant and how to ask where the bathroom was. My Spanish crash course had failed me.
“No Espanol, discuple,” I said. I looked behind me and then behind him. It was pitch black, and we were standing in a backstreet of Havana that Hollywood told us to fear. I continued to knock on Mildred’s door. A little louder this time. More people moved in the shadows. The man smiled at me and pointed to the doorbell.
All he wanted to do was help two clueless gringos find their way up to their room. I thanked him as he walked away, disappearing into the dark Havana void. The door opened. We were greeted enthusiastically by Mildred’s father – the resident cook, we would later learn. He spoke Spanish to us. We smiled. Had no idea what he was saying. He welcomed us inside.
Up the stairs was a beautiful home, filled with art, statues, and a Victorian-era feel. For the first time this entire trip, I tasted a real coffee. A super strong espresso. Mildred’s father made a cup for Sam, and Sam politely took a sip even though she hated coffee. When he had his back turned, I quickly finished it for her. It was only a few minutes in but Mildred’s home felt like our home. Cubans have a warmth towards strangers than can only be rivalled by family. Mildred’s father – and no, I don’t know his name – proceeded to make us breakfast. Breakfasts in Cuba are massive if you stay at a casa. Each morning, we received omelettes, ham, cheese, large portions of mango, banana, dragon fruit and pineapple, cakes, bread, coffee and tea. We never could finish a breakfast entirely, and that’s saying something – because I can eat a disgustingly large volume of food.
Mildred lived with her boyfriend and her father. She had the most pimped out apartment you can think of. Three stories, and right beside the Russian Orthodox Church. We had views of the ocean and the ancient Caribbean skyline of Havana. The room we stayed in was spacious. We were eager to hit the ground running in Havana, as we had heard so many great things about the city. After a brief nap after the worst flight we had ever been on in our entire lives – Tame Airlines, pardon my French, is a piece of shit (extremely rough flight from Quito, people gasping onboard thinking the plane was going to split in half, and oh, the electricity constantly going out so everything was pitch black in the cabins; this included the emergency signs and even the seatbelt signs above our heads… those life-saving lights that presumably have a backup generator) – we thanked all known deities and made our way through the dirty streets of Havana.
Children played football as old American cars rode on by. Most were in showroom condition. Bright pink, blue, purple, yellow, and green cars took us back to the 50s. The poverty was obvious but unlike other places in the world, there wasn’t a seedy underbelly present. Cuba supplies food rations and free health care (it’s top quality) to its citizens. So even in the face of poordom, people don’t starve and if they do get sick, they’re taken care of. Old dilapidated buildings appear half finished or half demolished, however you wish to look at it. Pastel greens, pinks, and yellows are applied to the exterior of old buildings. Men constantly ask you if you’d like to buy a Cuban cigar. Taxi drivers constantly ask you if you want a taxi. It’s impossible not to get one. There are more taxis than tourists in Havana.

The food, outside of the casas, isn’t great. You can pick from chicken or fish, beans or rice, maybe a side salad if you’re lucky. The hotels charge a lot of money for similar dishes. Staying in the casas is best since you get a genuine feel of what it’s like to live as a Cuban, and you also receive home cooked meals, some of which have been the best meals we’ve ever had. Big, big lobsters spill over your plates at dinner time. So large that no sides are needed, and it’s a mammoth effort just to finish it. Sam paid $9 and received three lobsters on her plate – now that’s what I call value! As big as the lobsters are, this is Cuba, and ironically you will NEVER go hungry. We were given delicious soups, breads, side dishes and mojitos until we couldn’t move anymore. It was ironic that in such a depleted country, we felt like we were eating like kings. Lobster is a staple dish. Something I could get used to.
We went to the Revolution Museum and learned about America’s assault on Cuba, according to Castro. Evidence of the CIA trying to blow up, attack, or infiltrate Cuba was demonstrated on the walls. Evidence of Cuba fighting them off was proudly displayed. The Americans were never referred to as such. The term “Imperialistic Yankees” was used throughout the museum displaying Che Guevara merchandise for sale, anti-American books about American foreign policy arresting the economic, political, and social rise of Latin America, and many remnants from the Cuban Revolution are shown. At the end of the museum is a wall with caricatures of American Presidents that Cuba hates. Batista started the wall off and while not American, he was a puppet inserted by the Americans. He eventually went on to commit genocide against his own people, which led to Che Guevara’s legendary mission of overthrowing the dictactor. In essence, Che saved the Cuban people from a mini Hitler. Cubans adore him for it. We didn’t get the impression that Cubans particularly love Castro, though.
A few other Presidents made the wall, such as Ronald Reagan and George Bush. All were referred to as cretins. All had reasons as to why the Cubans didn’t like them. It wasn’t that far off the mark, since Reagan’s Guatemalan episode and George Bush just being, well, George Bush, hasn’t won them fans in the Western world either. Cubans like Obama though. Maybe progress is in sight. Cubans also don’t hate Americans, so we aren’t sure who perpetuated that myth. I was told by one guy though who was trying to sell me a ride in his old American car, that since I was Australian he would charge me half as much as he charges Americans.
History is written by the winners apparently, and is a polluted concept due to the subjectivity and agenda of those writing it. Is America’s recollection of events in Cuba right, or is Castro’s? Australians tend to sit on the fence with politics, since we believe that all politicians are full of shit, so we enjoyed seeing Castro’s version of events after hearing America’s. It was eye-opening, and if what we read was true about the CIA’s black op missions, then anti-Cuban sentiment would be like the pot calling the kettle black.
The politics of Cuba make it an attraction for people all over the world. Unfortunately, there are heavy restrictions for Americans. Cubans welcome them with open arms, but the US government doesn’t want its people to contribute to the economy it has been trying to crush for 60-odd years. Still, a few Americans manage to slip in via Mexico. There are no problems. Cubans offer to not stamp American passports so that they don’t get in trouble back home. One day Cuba will open more, probably relax its stronghold on its own people and allow them to travel more freely. Communism/Socialism might disintegrate, but hopefully it still retains its old world charm. It would be mortifying to walk down the street and see a Mcdonalds, or a KFC, or God forbid – a Starbucks. Everything changes in the world, and one day Cuba will too. Its attraction is therefore temporary, and if you want to see what the world really was like all those decades ago, then get there now before it’s too late – because once Cuba integrates with the rest of the world more openly, everything I’ve just written will be nothing more than a reminder of how things used to be.
And as great as that will be for the Cubans, it’ll be a lost experience for all you travellers out there….
I have always rooted for lifting the Cuban embargo. It’s ridiculous. But fortunately for me, I have dual citizenship (and so are my two sons)! I can freely enter Cuba and heck have them stamp my passport too;). Thanks for this post. I really enjoyed reading it!
Thanks! I have plenty more coming up about Cuba – it was such an eye-opener. I’m glad you guys can all go, you will absolutely love it! What country do you have dual citizenship with??
I have both US and Philippine citizenships. My husband is the only one who is not dual citizen (just American). Looking forward to more posts! I’ve always wondered about Cuba and hope someday I will visit this exciting country!