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October 12th 2017
Published: December 13th 2017
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Cuban Roadtrip

Here I was with my Dad, waiting to see if we'd be getting on the flight from Montreal to Toronto. I had never flown standby before. My brother Shawn is a flight attendant with Air Canada and we were trying to meet him so we could catch a connecting flight to Havana, Cuba. With one seat left it wasn't looking good, so right before the doors closed, it was decided that I would board the plane and my dad would try for the next flight, about an hour later. After witnessing an argument between two boarding staff, I was off. Shawn and I arrived in Toronto at about the same time. Once we met up we headed straight for a flight lounge, compliments of his Amex card membership. We got drinks and dug into food until dad arrived. We all met up and then migrated to a different wing of the terminal, and then Shawn brought dad into a different lounge (his membership allows only one guest at a time). We boarded our flight to Havana without issue and as an added bonus Shawn used one of his special passes to get dad and I into business class, yet another first for me. The flight was awesome and we got full course meals and Ipads to view movies.We touched down in Havana about 3 hours later, amidst darkness.

Cuba has been high on my list of countries to see for a while and I welcomed the hot and humid weather with open arms. Located in the Caribbean Sea, Cuba is the largest island in the region and is home to 11 million people. Once a Spanish colony, Cuba gained independence in 1902 and became a republic. This devolved into a dictatorship state in 1952 which lasted a few years until the 1959 Revolution. Following the revolution, Cuba became a communist state with strong ties to the Soviet Union. The United States placed heavy sanctions and an embargo on this island nation in protest. To this day, Cuba is one of the last communist states in the world, and this along with the ever present embargo make a visit here quite unique.

Havana or La Habana as it is known locally, is the capital and largest city in the country. As we left the airport, we met Judith. She was a local who had spent some time in Florida and had got to know dad while there. They had corresponded and planned for a visit and that's how we had begun to plan out a visit here. Judith had many credentials to her name including working in radio broadcasting, working in the travel industry, being a certified scuba dive master and being a photographer. She took some time off work and was willing to spend some time showing us around her country and giving us a local perspective of Cuban culture. We met Manuelito, who would be our driver for an upcoming roadtrip, and walked over to his blue 1952 Chevy Sedan, a popular model in the country and one that you picture when you think of Cuban cars. We spent the next half an hour driving towards the city center where Judith had an apartment. She explained lots of facts about Cuba along the way. Once we arrived, we settled into her place before quickly falling asleep.

I awoke to the sound of hustling and bustling on the street below. I heard loud Banshee sounding noises coming from nearby. I thought they were normal sounds until I later learned that they belonged to a mentally disturbed individual who lived next door. I walked out to the balcony and looked at all the people and cars going about. Dad and I grabbed our camera's and began to shoot some street shots from above. Then we woke Shawn up and decided to go for a short walk to the seafront, which was only about two blocks away. It had rained heavily earlier, but now the temperature was heating up fast and the sun began peaking through the clouds. After our short stroll, we headed back to Judith's place and noticed that she had just arrived. She had spent the night at her Mom's place, whom she was helping care for due to advanced dementia. We all went out for a very late breakfast at a cafe, and then Judith took us on a tour around Havana. We walked for several hours through central neighborhoods and the capital districts. We saw a lot of colonial architecture, often with Spanish thatched roofing and colours. We walked past several famous squares, and then walked into a hotel and made our way to the rooftop on the sixth floor, giving us views of Havana from above.There was live Spanish music and we had Pina Colada's and Mojito's, just because we were in Cuba. They were really good. We carried on walking for a bit until Judith and Dad got picked up by Manuelito. They were going back to the airport to pick up Zizi, Dad's uncle, who would be joining us for a bit. He was flying in from Florida. Shawn and I walked around for about two more hours, mostly along the waterfront. By the time we made our way back to Judith's, they had all arrived and were hanging out in front of her place. We greeted everyone and then Shawn and I moved our stuff across the street to a Casa Particular, since there wasn't enough room at Judith's anymore. Casa Particular's were first allowed in the late 90's by the Cuban government, and are private rooms that locals can rent out. In many ways they reminded me of a kind of bed and breakfast, although often meals are extra. We went out for a short walk in the evening and Judith led us to a tasty restaurant for dinner. We had a few beers there too. Then Dad, Judith, and Zizi headed of to find some sketchy person to exchange his American money he had brought into the CUC currency. The Cuban government created the CUC, short for convertible peso, as opposed to the CUP which is used by locals. The CUC is pegged to the American dollar and was introduced to counter the use of American currency, which usually isn't accepted anywhere in a strange dichotomy compared to the rest of the world. Unfortunately since foreigners are forced to use this currency, it makes travel in Cuba lot more expensive. Shawn and I returned to our Casa for the night.

We woke up early and made our way to meet up with everyone. We walked over to a hotel near the waterfront and had a buffet breakfast that was pretty decent and cost about 5 CUC. The AC had broken down and the place was a sweltering mess. We continued on to meet up with Manuelito and his 52 Blue Chevy Sedan. We were about to begin our journey to explore more of Cuba, but first we really needed to get more CUC currency, as the small amount we had converted was already almost out. We got to a bank and exchanged the last of our CDN currency. Then we were off to the west, to the province of Pinar Del Rio. The journey took us about two hours and luckily the car was spacious enough for the six of us. The scenery began to turn into lush greenish hill country. This region was home to numerous tobacco plantations that produce Cuba's famous cigars. We arrived in the town of Vinales, which not too long ago was just a simple village. On the way in we stopped at a hilltop to get an incredible view of some scenery. We spent some time here before continuing on to Daniel Y Martha's Casa Particular, which had been recommended to Judith by a friend. The family seemed really nice and we stopped only long enough to drop our gear off before heading back out to visit one of the previously mentioned tobacco plantations. We got to tour a local plantation and learn about the process behind the production of cigars and then had some sample cigars, which turned out to be smooth and mild. Shawn and I bought a pack of twenty to enjoy during the rest of the trip and once we returned home, if there were any left! We then went to a nearby location to explore some caves. The caves were made out of ancient limestone, as is much of the rest of this mountainous region. We went down through an illuminated walkway and then took a short boat ride until reaching the opening the fed into a lagoon. After this we went back into the center of Vinales and walked the main street for a bit, checking out people and the shops. I noticed more tourists here, although Judith told us tourist numbers were quite low for this period. We went of into the countryside once more to an area on a small hill so that we could catch some glimpses of sunset. Then we returned to our Casa Particular and had showers before sitting down to to a homecooked meal of Cuban style cuisine consisting of beans, rice salads, plantains, yuca, as well as incredibly grilled and seasoned chicken legs. The food was awesome and afterwards I chatted with some of Daniel's family and friends and was happy to realize that my conversational Spanish was coming along fairly quickly.

We had an early breakfast at the Casa and then went back to the main street of Vinales. Our goal for the morning was to meet up with a guide and his horses and ride for a few hours. We waited for a while but no one was showing up. Turns out that Judith had mistakenly made arrangements over the phone with a guide in an entirely different province. I guess it made sense that he couldn't find us! We ended up going back to the place where we saw the previous evening's sunset and climbed the small hill, where we waited for some horses to arrive. After a few moments a caballero came riding up with several horses. We greeted him and then were each given a horse. The day was already growing hot and we were sweating. Our guide didn't really give any of us instructions on how to ride our horse but my riding experience from years past in Mongolia quickly came back to me and I was handling the beast with ease in no time. Dad was freaking out because he was having issues controlling his horse. Shawn's horse seemed to want to follow Dad's horse. Zizi and Judith seemed pretty comfortable on theirs. We went down a dirt road at first, generally going at a trot. We veered from the road onto a dirt path, passing fields and animals. Then we began to ascend, higher and higher into the mountains. It had been raining on and off and the trail was muddy and several deep ponds of water lay in our path. The horses powered through them without concern or bother. Dad was yelling and wearing throughout and we awere all laughing at him. We finally reached a clearing and small house lay in the middle. Once the horses were tied up, we ran to the house and took refuge as the tropical rains descended. We had a beer there, and once the rains abated, we went for a walk to see some caves. We found a small pond after a steep climb down. The water was cold and the mosquitoes were abundant. Then the rain returned and we got soaked on the walk back. The horse ride down was precarious at many points. Dad was swearing even more on the way down. In fact, we claimed that he hit his swearing quota for the year. Once back on the road, I got my horse to gallop all the way to our initial starting point. On the way I got chased by a dog and had to push my horse to gallop even faster! We ate lunch at the hut on the hilltop, served by some cute Cuban women. Manuelito, always keen in the presence of "chickas", began chatting them up. We left quite late and made our back to the Casa Particular to get our stuff, then we all piled back into the 52 Chevy and took off, heading back towards the east. We probably should have left earlier but what else is new!

We backtracked to Havana, where we stopped at Manuelito's uncle's place to get fuel. We met some of his family, including his 92 year old grandfather. I was able to have an actual decent Spanish conversation. Soon after, we were back on the road again heading towards the south of the island, into the province of Matanzas. Our destination was the town of Playa Larga, at the top of the Bay of Pigs. This is a place that holds special importance to Cuban revolutionaries, who are said to have repelled an American backed insurgency. It was a five hour drive and we got caught in some rain and darkness. We stayed at a nice Casa Particular with some really sweet rooms. We had a light supper and then I walk with Manuel to a nearby bar to get a beer. We returned back and later we all took off and walked the beach for a while, save Shawn who was exhausted and went to sleep. Overnight it rained a ton.

The next morning we woke up to a lot of rain. The sky was cloudy and everything was drab. Apparently there was a tropical storm moving across from the south that was heading towards Mexico. We had been thinking of doing some diving but this would be postponed thanks to the rain. We drove towards the nearby town of Playa Giron and on the way we stopped at a cove. The water was really clear and people there were practicing with scuba diving but the mosquitoes were tenacious and we couldn't stay there for long before they began ripping us apart. Once in Playa Giron, we visited a museum that showcased the Cuban revolution. When we got back outside, the weather had improved so we went for a walk along the beach. The waves were violent and slamming into the shore. We did a bit of photography and then went to a nearby locals house who's backyard was set up with bird feeders. Many hummingbirds came to feed there and dad and I spent time trying to capture them with our cameras. I had a pretty tough time. We then went back to our Casa in Playa Larga.

The next day the weather was much better and that meant I would be able to take a crack at diving. We drove down along the coast to a place called Punta Perdiz, where Judith had some diving contacts. Cuba is famed for its diving, although Hurricane Irma, which had hit the Caribbean several weeks earlier, reigned havoc on the diving scene here. I hadn't gone diving since I had been in the Maldives a year and a half earlier. Shawn would be joining Judith and I, and it would be his first experience. We suited up, got our briefing and then got to it. I was paired with Judith, while Shawn would be going with another instructor and a tourist from Europe. As I'd expected. the visibility had really taken a hit. Tropical fish flocked around us as we descended deeper and deeper. We went along the coral. Shawn began having trouble regulating the pressure in his ears and ultimately had to abort his dive and go back to the surface with Judith who had been trying to help him. I continued on with the others for another half hour. After the dive was completed, we all hung out by the water and went swimming for a while. We continued on to the coastal town of Cienfuegos and checked into a beautiful Casa particular right along the water. Shawn had realized that there was Wifi available at the back of the Casa, and his internet rehab streak effectively ended. I decided to refrain, it was really nice to be disconnected. We then went for a walk in the immediate surrounding areas. We visited a beautiful building with Mugal architecture that had been made into a hotel. We had a drink up here and Zizi, Shawn and Judith discovered that there was Wifi too. They quickly descended into a robotic drone like state while staring into their phones. We ate at a pretty nice restaurant right next door from our Casa. That night we went out into the town and stopped by a disco club, although none of us really cared to go in. The disco scene certainly isn't my scene.

We were set to explore a bit of Cienfuegos today and went into the main square. The buildings were made up of beautiful colonial architecture. We stopped into a small cafe where we had some Mojitos while watching an incredible guitar and singer performance. I've been loving the Latin and Flamenco style guitar here! By midday, we were headed to Trinidad, in the central province of Sancti Spiritus. Along the way we stopped for some fruit from a roadside vendor. Trinidad is a small village further east near the coast that had become popular with foreigners. Within moments of entering, there was something that was captivating me about this place. The cobble and narrow streets seemed beautiful. We walked the town as the sun was going down. We ran into a really cool band performing famous Cuban tunes on an outdoor stage near one of the squares, with dozens of people sitting around at tables drinking alcohol and smoking cigars. For supper we went to a restaurant across our Casa that was guitar themed. I had a fish dish while a man/woman duo sang and played acoustic guitar. After dinner the guitarist let me use his guitar for a bit, and I stuck around and noodled on it while the others went back to the Casa across the street. That night Manuelito gave us life lessons about "chickas", and both Shawn and I went to sleep relatively early. Dad, Judith and Zizi stayed up outside with a bottle of Rum.

I rose early and went to get Judith and Dad. We had agreed to start the day with a morning walk through the streets of Trinidad. We saw people going about their morning, school kids in uniform waiting for the school doors to open, shops opening up, and ration stores receiving supplies. The light was great for photos. We returned to the Casa for a late breakfast then went back out for the day. We had to make a bank stop, and since Dad was the only one who's card was working while in Cuba, he was the one who was pulling money out, while the rest of us would be paying him back when we had access to more funds. Soon after, near the bank we walked to our blue Chevy, and lost Dad for a while as he got carried away taking photos. We drove around and eventually found him. We were now on the way to a valley outside the town, and arrived at a market with a large tower. We got a sugarcane drink from a vendor here and then walked along the merchants who were all trying to sell us mostly useless crap. We also met a really weird middle aged Cuban woman who was hitting on us and openly telling us she wants to meet a Canadian man to take her to Canada with him. Not my cup of tea. We climbed the tall tower and had beautiful views of the surrounding mountains. Then we went to check out a canopy zipline. There was 4 different ziplines of various lengths and heights. Shawn, Judith and did the ziplining. Judith had been excited to try it initially but then almost backed out due to fear, but I managed to convince her to go for it and she did. After this we continued on to a beach and everyone took a turn to swim. We had some awesome Pina Coladas as the sun was coming down. We were close to a small fishing village and went to a restaurant that Judith recommended that specialized in sea food and fish. There was a pretty good live band playing Cuban music and the guitarist let me jam with his guitar for a bit. After dinner I sat with Shawn at the bar for a bit. Once we arrived back in Trinidad, Manuelito decided he would try to hit on a group of young women who were walking along the car...with all of us in the car watching. We ended up going to a nearby square and buying some wifi cards (on the black market), and I stayed with Shawn in that square as it was a wifi hotspot and we needed to get online to see what the flight loads were for our eventual return home. Lots of people hung out in hotspots such as this late into the night, and it seems like having internet in one's own home is incredibly rare in this country. We walked back to the Casa soon after.

We woke up and had another nice breakfast at the Casa before piling into the car and making our way out of Trinidad. We traveled through some incredible jungle scenery as we headed north. We then passed several villages and seeing horse drawn carriages became the norm.We made a stop in the city of Santa Clara, right in the middle of the island. There was a famous monument dedicated to Che Guevara, the Argentinian born revolutionary who traveled to Cuba and was instrumental in overthrowing the Batista government and ushering in a socialist state. We then went into the museum, which showcased his life from beginning to end. I must admit that really didn't know all that much about Che but I learned a hell of a lot after this experience. He really led a hell of an interesting life. We then went into a tomb which housed the ashes of Che. After that, we got back on the road and headed east towards Havana. We got back to Judith's apartment in downtown Havana and then took the rest of the evening easy. Down the street from her place was a busy pizza place and I headed down and used my Spanish skills to order pies for everyone and then brought them back. I picked up some beer too. Later on we took a walk down the seafront were plenty of locals would congregate. We got plenty of whistles from hookers trying to get some business!

I woke up to the sound of Banshee cries and remembered that this was coming from Judith's neighbors place. Then I remembered that today was my birthday! We went out to that hotel restaurant that we had visited a week prior and had breakfast. The AC still wasn't working and it was sweltering inside. As we were finishing up, a piece of ceiling over the buffet area collapsed. Everyone looked dumbfounded. Another day in Havana I guess. We stopped by Judith's apartment and then headed out again in search of a bank to restock some funds. We took a bunch of photos along the way and somehow Zizi, Shawn and I got separated from Dad and Judith. We continued to the bank that we had gone to a week earlier, thinking that they would meet up with us there. They never showed up. After about an hour of frustration, Shawn and I headed back to Judith's apartment, and found them there. We then went back to get Zizi. Everyone was pretty annoyed at this point. We walked along several interesting Havana streets, and got close to the waterfront. We explored some interesting squares and stopped to have some beer. Then we headed over to the nearby Havana Club distillery, and went on a short tour to learn about the distillation process of this famous Rum. Dad got yelled at for standing places he shouldn't have been while trying to take some pictures. Shawn ended up buying a bottle of Rum to take back with him. Later that night we had plans to go to a buffet dinner restaurant in honor of my birthday. Manuelito and his wife surprised us and would be coming along with us too. At this point, Judith wasn't feeling good and had a bad headache with nausea. She was lying down and we told her to take it easy and not worry about coming out if she was feeling ill. Dad decided to stay with her and they would walk over if she began feeling better. The rest of us went to the restaurant and began eating. The food wasn't bad and we had gotten to desert by the time Judith and Dad showed up. The night would have continued on but Shawn and I had a flight to catch early in the morning and decided to be lame and try to get a few hours of sleep before leaving.

We woke up at four in the morning, gathered our stuff, and then waited outside for Manuelito to show up for a ride to the airport. Banshee cries were heard next door as we waited. Manuelito eventually arrived and then we headed to the airport amidst the darkness of night. We checked in and got onto the flight without any issue. Shawn got us into business class, although the Cuban food they served us was pretty awful. At least we got Ipad's for the flight back to Toronto. Once in Toronto we headed to a lounge and got some food. Both Shawn and I were having some issues with our intestines, not sure if we ate something suspect the night before. We sat side by side in the bathroom stalls and emptied our guts with explosive diarrhea! A great way to cap off the trip. Then we headed our separate ways with Shawn heading back home to Calgary and I heading back to Montreal. I had a great time in Cuba and will return hopefully sooner than later.

Additional photos below
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14th December 2017

We enjoyed our time in Cuba and want to thank you for the memories.
14th December 2017

I always enjoy a fellow Canadians perspective on my favourite place in the central Americas. Great trip! Great photography!
14th December 2017

Thanks! I will definitely be going back again, awesome country from what I experienced!
14th December 2017

Cuban colours
Your photos are so expressive and beautiful! How lucky to have a local take you around their country... I enjoyed your adventures, and although I felt bad for your dad on the horse ride, I did laugh a bit :) Cheers, Ren
14th December 2017

Yeah we laughed at him the whole time too!

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