I’ve been dreaming about visiting Cuba since I was a teenager. Living in Mexico gave me many opportunities to visit some incredible places. I went across the Yucatan peninsula many times, explored Cozumel Island, visited Mayan ruins, and went to Peru.
It was my last month working for the Cruise Lines. At this point, there were still two big trips that I really wanted to take. The week that I had left was too short to get to the most remote destination on my bucket list. But, I had enough time to hop over to the next Island on the map – Cuba.
At the time, my partner was visiting me. She took it upon herself to do all the research and planning for our Cuban adventure. There is one big lesson we learned after the Cuban experience… You can’t trust everything you read on the internet – not even from official government websites.
The Cuban Visa Disaster
Being South African, it is sometimes really hard to get a visa for some countries. There are very few countries that an SA citizen can actually enter without a visa. But, according to many online sources, Cuba was one of them.
The instruction was simple – show up at the airport, and upon check-in, you will get a visa for 20 dollars… Great!
So, the night before leaving for Cuba, we stayed over with friends in Cancun. And around 6 am the next morning, he took us to the airport.
Checking In For Our Flight to Cuba
We excitedly walked up to the check-in counter and a guy approached us with a booklet full of visas. I could see his expression change from cheerful to uncomfortable when he looked down at my green South African passport. “I’m sorry, but you need to get your visa from the Consulate.”
Needless to say, we suddenly felt all kinds of emotions ranging from anger to panic. We’ve already paid our tickets there and back, a cabaret show in Havana, and all our accommodation! Missing this opportunity to go to Cuba was simply not an option.
We hurried over to the flight booking counter to see if we can reschedule our flight for later. Re-booking the flight would cost us more than the entire return trip for two! So, we decided to head to the consulate to sort out the visa before re-booking.
Our Mission to the Cuban Consulate
We jumped in a shuttle that took us to the embassy in downtown Cancun. We walked down the street and finally found the consulate among houses in a residential neighborhood. Guess what? It only opens at 9 am! Our original flight was at 8 am. Now we had to wait another hour for the consulate to open before we would know what our fate was.

Not having any other options, we sat down in the park across from the consulate. I recorded a “not-so-happy” message to our South African president after reading the front page of my passport.

The consulate finally opened, and after speaking to a consultant and getting all the forms filled out, I had to make the payment… in a bank… somewhere in the main road of Cancun. We walked for what felt like an eternity and finally found the bank and made the payment. We then headed back to the consulate to finalize the Visa.

Check-in Round Two

Another 300 peso ride back to the airport and a super expensive replacement ticket later, we finally made our way through the gates.
At this point, we were already exhausted and starving, so we grabbed some food before boarding the plane.

We’d spent most of our cash on getting to the consulate and back, and paying for the visa. So, I quickly googled whether we could draw cash at Cuba’s airport.
I usually find it much easier to draw cash in the country that I’m visiting. That way, I don’t have to go through the currency exchange. After scanning through many articles, I felt assured that drawing cash in Cuba would not be a problem.
Finally on the plane, we both passed out from utter exhaustion and woke up as we were landing in Havana.
Cuba… Finally!
Arriving in Cuba, we went through immigration and a baggage check. We made our way to the ATM’s that came so highly recommended on the internet, and… “Transaction denied”. We were both working for an American company at the time and had US bank cards. And, of course, you cannot withdraw money from a US bank account in Cuba!

With only 27 dollars in our pockets, the panic set in. We stumbled over to the currency exchange and got a total of 23 Cuban currency (CUC)… and a few coins.
A taxi ride from the airport to our Airbnb would cost 30 CUC. We spoke to a few taxi drivers and heard of a hotel where you can withdraw money from US bank cards. So, we convinced one driver to take us to the hotel so we can draw money and pay him for the ride.
At the hotel, we had absolutely no luck drawing money either. So, we handed over all that we had and apologized to a very upset taxi driver that we couldn’t pay him the full fare.
Booking.comMaking Our Way to The Airbnb
In front of the hotel was a boarded map of the area. We took a photo and planned our route to get to our accommodation.
We walked… and walked… and walked through the winding roads – starving, sweaty, and exhausted… and flat broke.
About one hour later, we finally arrived at Casa Dana and a very concerned host. In my broken Spanish, I told her the whole story. She was kind enough to get us an internet card and gave us 10 CUC to get something to eat.

The Desperate Hunt for Money
Now, when it comes to the internet, Cuba is quite a different experience. If you walk through the streets and suddenly see a bunch of people standing around on their phones, you know you’ve found a hot-spot. You get an internet card and can connect only in areas that have service. Luckily, we were close to a hotel that had internet.

We immediately started sending messages to all our friends on the ships and in Mexico to see if someone could help. The problem is that you cannot send money to Cuba with Moneygram or Western Union. Although many of my friends were willing to help us out, we simply couldn’t collect it in Cuba.
I was just about to call it a day when I remembered that one of my ship friends mentioned earlier that week that they would be docking in Havana. In a final, desperate attempt I sent him a message. And, he responded with “We’ll be docking there tomorrow.” What a relief! I told him about the situation and how much money we needed. He agreed to help with as much as he could if we met him at the pier the next morning.
Day 1 – And We’re Done!
Knowing that we would be getting some money the next day, it was time to settle down and get something to eat. After taking a long-overdue shower, we walked around the neighborhood in search of a burger place our host recommended. With our stomachs finally satisfied, I sat down to write down our crazy experience.
Absolutely worn-out and defeated, we finally settled in for a good night’s sleep. The next day we would take on the streets of Havana on our pilgrimage for gold.
Day 2 – Conquering the Streets of Havana, Cuba
The next morning, with two bottles of icy water and no breakfast, we headed out. And so started our mission to walk to the Cruise ship terminal.

We were immediately in love with the city. The amazing architecture, colors, people, and cars. There is no better way to truly experience a new destination than on foot.
We walked through the streets and squares, taking photos as far as we went. We pushed our way through the crowds in the narrow, crazy pathway leading through china town. And finally, the Capitolo exposed itself. Regardless of our financial predicament, it was an amazing feeling to finally be walking the streets of Cuba.
We reached the downtown area after about 3 hours of walking in the humid heat. It was clear that we’d entered the tourist zone and that the ship just docked.

Meeting Our Savior
When I saw my friend waiting on the stairs of an old Havana building, I almost dropped at his feet with gratitude. He’d asked all of his fellow team members on the ship to help sponsor us and managed to collect a few dollars and Euros from them.
He then took us to an ATM in the downtown area to see if we can draw money there. But, again, our cards wouldn’t work. So, he drew some of his own money to help us get through the week. We sat down for breakfast and then parted ways again.
Marina and I made our way back to the house. Relieved to know that we could now survive the week, we took our time walking back. This time, we walked along the coast and through downtown Havana.

Time to Adjust
On the way home, we stopped by local markets to get some food. This is where we discovered that Cuba actually has two currencies. CUC is close to the dollar’s value and is mostly used for tourists. But, CUP is Cuban Pesos that is used amongst locals in non-touristy markets. It’s about 25 CUP to one CUC.
Shopping off the grid saved us a lot of money that week! We managed to get eggs, bread, sausages, some fruit and veg, and a beer for a couple of CUC.

Back at the house, it was time to re-evaluate our financial status. Before we came, we planned to each put in around 500 dollars spending money. This would give us more than enough to luxuriously enjoy our time in Cuba. My friend gave us a total of 350 CUC. Now, we had to figure out a budget to get from Havana to Trinidad to Matanzas, and back to Havana.
Marina did a “guestimation” of what our transport would cost. Finally, she told me that we had a total of 15 CUC spending money per day between the two of us. That 15 CUC had to feed us and cover whatever else we needed to do every day.
And then… this happened!
After resting a bit and taking a much-needed shower, Marina went to buy some sugar for our coffee. She returned shortly after leaving, and without a word, disappeared into the streets again with a plastic container. Turns out, you had to bring your own container when buying certain things (like sugar) from the street-side market.
She brewed us a cup of coffee and then came to sit with me on the porch. As she came outside, she closed the door behind her. She instantly grabbed her forehead in disbelief. It was one of those doors that locked on its own when you pulled it shut… And, the keys were inside!
We circled the apartment, but the owner made sure that there was no way to get in without a key. Eventually, we knocked on the neighbor’s door. She then called the owner, who told her that the other neighbor has a spare key.
Finally, we got back into the apartment and started getting ready for the evening.
Attending a Cuban Cabaret
That night we had a reservation to go and see the famous Cabaret at Tropicana in Havana.
Knowing our budget, we decided not to take a taxi, but leave early and walk all the way there. After about an hour of walking, we soon realized that we are either lost or heading in the wrong direction. Finally, we gave in to our pride and flagged down a taxi to take us the rest of the way.
At the entrance, we were given Carnation flowers, cigars, and a bottle of Havana Club rum. We made our way to the open-air theater and sat down at a shared table. We had a pretty good view of the show and the rum managed to take off the edge. The show was a welcome change of pace after the crazy two days we just experienced.

As we left the show, the taxis were lined up outside of the entrance. With our budget in mind, we asked for their rates. But, it was well out of budget, so we started walking up the street – admitting the reality that we will now have to, somehow, make our way back home on foot.
As we started walking, one driver ran up behind us. He offered to take us in his classic Cuban car for half the price.

It was the best part of the day! The rum had already taken effect on our empty stomachs and we were so grateful to not have to walk again. To top it all off, the drivers were young, energetic, funny, and playing some really good tunes.
After an eventful drive, we came to a stop in front of the house. I handed him the money and we got out of the car. Moments later, he came running after us again. Instead of CUC, I gave him CUP which is much lower in value. Laughing at our stupidity, we fetched the right currency from inside.
The Next Stretch – Havana to Trinidad
Feeling revitalized from the Cabaret show (and the rum) the night before, we packed our things for the next stretch of the trip.
We walked to the taxi stand and hopped into a car for our 4 hour trip to Trinidad. Marina’s guess on taxi fare was right on par! We made a quick stop in Cienfuegos to stretch our legs and then took on the last hour of the trip.
As we drove into Trinidad, it was a completely different world. The city streets were narrow cobbled stone pathways. There were fewer cars, more horses, and the people seemed less friendly and more pre-occupied with their day-to-day lives. It was clearly raining earlier, so the streets were filled with puddles and the lingering smell of wet horse manure.

Our accommodation was comfortable but didn’t have the kitchenette we thought it had. So, we had to convince the landlady to use her kitchen. She was a bit surprised at first, but after we explained that we cannot afford to eat out, she soon warmed up to the idea. There was a cozy little garden behind our room where we sat down to enjoy our lunch.
Booking.comWe ventured into the streets to explore. It was clearly a city that attracted a lot of tourists. We weaved through the streets, past an old church, and found a side road filled with the most interesting art shops and cafés.

We explored the city, spoke to some locals about interesting things to do in the area, and then headed home.
Day 2 in Trinidad
Early morning we ventured out in search of food and found a conveniently close street-side stall. We bought some food supplies and walked around asking about horse-back riding tours. Back at our accommodation, we made breakfast and prepared some sandwiches for the afternoon that lay ahead.

After breakfast, we went to meet with our horse-riding guide for the day. We waited while he went to fetch the horses and got them saddled up and ready for us.

At first, we walked for a while so that we can learn to connect with the horses. And then, we hopped on and started the peaceful ride towards a waterfall.

We made our way up the hills, through a forest, and past some local “watering holes”. Then, finally, the waterfall appeared through the trees.

There were quite a few people, but it didn’t feel crowded at all. We enjoyed a swim in the fresh, icy water, and soaked up the sun. We sat on the rocks to enjoy our sandwiches and took a few goofy photos.

Just as we were getting ready to leave, it started raining and all the people scrambled to squeeze in under the only roof there was.
Once the rain settled down a bit, we packed up and got on the horses for the ride back. Along the way, the rain started coming down stronger. Feeling adventurous, we decided to take on a gallop to the closest shelter. We hung out there for a while – playing with puppies and kittens while waiting for the rain to pass.
I’ve been on a horse before, but this was the first time that I spent a whole day riding and I definitely felt it the next day!
We would have loved to go to the beach while we were in Trinidad. But, it was too far to walk and our finances didn’t allow for taxi fare.
Trinidad to Matanzas
The next morning, we shared a ride to Matanzas with another couple. About half-way through the trip, we made a quick stop in Colon to stretch our legs and grab some snacks.
When we entered the city, the driver asked us to explain where we were staying. This is the moment I learned that you should always download offline maps on google before traveling – just one of my many tips for international travel that I learned the hard way.
We eventually figured out more-or-less where we were supposed to be and the driver dropped us at a mini-market on the coast just past the downtown area. From there, we walked a few blocks until we finally found our accommodation.
Booking.comThe house didn’t seem anything like what we’ve booked, so it took a while to find it. We walked into the property and found an old lady in the backyard. She called her son who was the owner of the property to confirm our check-in. We had to wait a while for the cleaner to finish and then settled down in our most luxurious accommodation of the week in Cuba.
If you looked at the property from the street, you would never expect to find this oasis in the backyard. There was a luscious garden, communal outdoor BBQ area, and a small outdoor table for each apartment.
As you walk through the stained-glass doors to enter the apartment, you have a big lounge with a hot tub. Upstairs is the bedroom, bathroom, and a kitchen that overlooks the lounge.
Exploring Matanzas on a Budget
Our initial plan was to visit the beach and caves of Varadero. But, because we were on such a tight budget, we decided to just explore and enjoy Matanzas instead.
That afternoon we walked to the shop where the taxi driver left us earlier and stocked up on spaghetti, meat, and tomato sauce. Spaghetti seemed to be the most affordable option to fill our stomachs and had become our staple food for the entire Cuba trip.
We spent the rest of the day cooking, hanging out in the garden, and enjoying the hot-tub.
The next day, we spent a lot of time walking the streets of Matanzas. We wandered into downtown, found a local bakery, and collected pebbles on a beach close to the house.

We also went in search of our next transportation option to take us back to Havana the next day. It was an extremely hot day and we were exhausted from all the walking and stress of the trip. So, on the way back to the apartment, we stopped by a small public beach to cool down and relax.
Back at the apartment, we finally got to meet our host. He was super polite, able to speak English, and very curious to hear about our crazy trip. He offered that we drove to Havana with him the next morning. But he was leaving a little early, so we decided to stick to our initial plan.
Matanzas to Havana
By now, we’d discovered that, like in Mexico, they have collectivo taxi services in Cuba. A collectivo is a shared ride – the more people in the car, the less you pay per person.

We walked for about 40 minutes to get to the collectivo station and found a taxi that could take us to Havana. While we were waiting for more people to join the ride, we grabbed a snack at the station.
By the time we got into the collectivo, our spirits were lifted. We’d made it through and were on our way back to Havana!
The coastal ride took us back into the familiar streets of Havana and to the door of our next apartment – another gem hidden in the suburban streets.

Back in Havana
Our host in Havana was a friendly old lady. She checked us in and showed us around the apartment. After settling down, we went for a walk to explore the new neighborhood.


On our last day in Cuba, we went in search of food again. We came across a building where a man was selling pasta through a window. My Spanish vocabulary seemed to let me down this day, so we resorted to some sort of sign-language.
He explained how much the spaghetti cost by weight, but I didn’t quite get what he was saying so we showed him how much we needed. He weighed it out and with pinched fingers and a squeak, indicated that we should add just a little more to make up the weight.
With spaghetti in hand, he then gave us a look we’ve seen before. It translated to “Where are you going to put it?” We quickly pulled our water bottle out of its casing and stuffed the spaghetti inside. It was the most animated purchase we’d made all week and his expression said it all… tourists!
Our Last Night in Cuba
So far, we’d done very well at sticking to our tight budget, so we felt like we deserved a night out. One of the places that we really wanted to visit while in Cuba, was El Cocinero. We’d actually chosen our last apartment because it was very close.

That night, we got dressed up and made our way to this famous restaurant. The hostess led us up a spiral staircase and into the open-air garden restaurant.

We scanned through the menu and soon realized that eating there was not an option – we simply couldn’t afford it. So, we had a beer instead and headed back to the apartment.
Leaving Cuba
Our flight back to Cancun was later in the afternoon, so we spent our morning relaxing and packing up our things.

When we reached the airport, we felt that we needed to at least try to find the taxi driver who took us on the first day. We scanned through every taxi and face to find him so that we could pay him what we owed but had no luck. We exchanged our remaining cash for Mexican pesos and actually had more left than what we expected. Sure, we would be able to do and see more in Cuba if we had our original budget… but this was an experience I wouldn’t trade for the world.
Our flight landed in Cancun, and we immediately made our way to an ATM to see if our cards were still working. Relieved that our accounts weren’t blocked, we withdrew some money and made our way to Isla Mujeres – my favorite Mexican Island.

That night we dined like kings and the next day we enjoyed the crystal-clear waters of the Caribbean.
It was such a welcome change after the stressful week we’d just experienced. There is a mixed community of locals and foreigners living on the island. The locals are friendly and the pace is much slower and relaxed. But, Isla Mujeres is a whole new story for another day.

Have you ever been to Cuba? Feel free to share your comments or experiences. And, remember to follow me on Facebook @onkeytravel
Wow, that was something of an adventure, the stressful parts included! I went to Cuba with a small group tour and there was a lot less hassle. But still a slightly crazy, remarkable country. It sounds like the new normal for overseas visitors is being segregated in a foreign-only resort. Seems like even Havana is off limits 🙁
What an experience 🙂
Oh my! One to remember for sure!!
Definitely… and one of my favorite stories to tell as well 🙂
Love all of your pictures with your story!
Sounds amazing, despite the pitfalls. Great travel tips, thanks!
Such an insightful post, thank you so much for sharing with us!
Awesomely interesting read, you seem to have a great time traveling to Cuba and Caribbean islands. The pictures were amazing!
Amazing 😍
Great story telling. I admire how you two rolled with whatever surprise sprung up with the trip, and there were many! I would live to visit Cuba.
Live and love to
Quite the adventure !!
what a crazy adventure!!! We had a similar ordeal in Crete when my ex husband’s bank card didn’t work. We made it through the trip fine until the mechanical failure on the plane and they delayed our return by a night. We had spent all our money- we had enough money to buy an apple to share and a yogurt. Definitely learned a good lesson there. 😂
You are so determined. So many people would have given up with all of those hurdles. I’m inspired. Thank you. BTW – You got a key & a free book download as a gift for being a New Member of our site. We’re trying to make sure our members don’t miss the freebie because it expires on Monday 😉
Wow that was such a wild ride! I really felt for you in all of the stressful parts but it seems like you handled it all really well. Putting Cuba on my bucketlist now!
Great adventure for sure. I hope to go one day. Thanks for sharing.
Beautiful pictures
Please subscribe my Blog and shower your love on my posts 🌼
Loved all the pictures of the cars! They look sick
What a GREAT post. I Love the photographs and have always wanted to visit Cuba. With the COVID-19 virus, I’m beginning to think my traveling days are basically over, at least for awhile. Thank you for taking a look at “A New Normal”. Please come back. Take care. B.
Nice post..Thanks for sharing good and bad experiences
Hi
Thank you so much for sharing your Great post
Wow! What an incredible in depth post!