Of all the places we’ve visited this year, Cuba is the most complex. Its hard to sum it up in a few words, but before I get into the details of what we did, here are a few overall thoughts:
- The Cuban people were absolutely lovely and welcoming to Americans. We felt 100% safe there. When we said we were American we always received a positive reaction, and often heard about an Aunt/Uncle/Brother/Cousin living in the US. We heard many times how happy Cubans were with the Obama era loosening of travel restrictions and how frustrated they were by the recent roll backs. For a short while, tour guides, restaurants, taxis, guesthouses, and marinas were busy serving Americans. Now they rarely see Americans. The impact is mainly felt by those we least want to hurt – small business people who started or expanded business to serve tourists, particularly those that speak English.
- Cubans are very interested in America’s Cuban politics. A number of people brought up Marco Rubio. They seem to have love/hate feelings about him – angry about his Cuba politics, but at the same time proud of a native son.
- Cuba is a large, mostly rural country. Two of the 11 million citizens live in Havana, the rest mainly live in rural villages and farms.
- The “Special Period” occurred in Cuba in the 1990’s following the collapse of the Soviet Union. There was mass poverty and hunger after the USSR’s economic support for Cuba faltered. This period still looms large in the hearts and minds of Cubans.
- Music and art is everywhere. Many restaurants we visited had live music, and art galleries and public art were omnipresent. And we loved hearing the thumping bass of music coming from cars and homes all around.
US regulations require visitors to Cuba to be actively engaged in organized activities led by companies approved by the US. So our experience here was more “vacation-like”, with tours and excursions vs. other islands where we’ve lived more like temporary residents. Here’s what we did on the first half of our trip…
Benvenuto Cuba!
We left Key West at 6pm for an uneventful 16-hour passage through the night. The winds were moderate, and the waves were low under cloudy skies. We had read a lot about entry into Cuba and given the American stereotype of Cuba being “scary”, I was a little worried and tried hard to follow the rules exactly.
At 12 miles off the coast, I called “Havana Morro” (Havana Port Control) on the VHF with trepidation. I expected a difficult call since we’re American flagged and I don’t speak Spanish. I was prepared to answer a set of pointed questions about us and our boat. I couldn’t have been more wrong. The port control officer simply welcomed me to Cuba and made sure that I knew how to get into the marina safely. It was a great start to our trip and the first of many stereotype bashing moments.

Customs and Immigration at Marina Hemingway (12 miles west of Havana) is in a nondescript, cement building along a concrete sea wall. We were welcomed by a young guy in street clothes grabbing our lines and welcoming us to Cuba in English. Next, three women came aboard Boundless in uniforms. They were somewhat stern, but friendly. Two didn’t speak English and mostly filled out paperwork based out our ships papers. The third spoke some English and was in charge of safety and medical. She asked me to show her some of our food stores and had me throw out an expired can (oops!). She looked at our bathrooms (not sure what she was looking for) and took everyone’s temperature. Unfortunately, Andy had a small fever, probably because he had just woken up from a deep sleep wrapped up in a blanket and sweating. She gave him three tries and suggested he drink water, wash his face with cool water, etc. By the third try, his temperature was close enough, so she let it go. Next, we went into the building ashore two at a time to have our pictures taken. These will be compared to when we leave to make sure we’re the same people. We were asked if we wanted our passports stamped (yes!) and were told Welcome to Cuba and Welcome to Marina Hemingway.
Customs and Immigration works closely with the marina and we were given our slip assignment by the guy who had grabbed our lines, along with a card for his favorite restaurant. Our first indication that private enterprise is alive and well in Cuba.
Marina Hemingway is a large marina complex with a series of 4 canals with boats tied up along the sides. There’s also a hotel, stores, restaurants and a bar. After we tied up, the Harbor Master asked to meet with Doug below while the rest of us waited in the cockpit. He went over the marina facilities, then asked for a tip. Doug had read about this and said no. That seemed to be OK and he left. Last, two guys from agricultural control came aboard. They also asked Doug to meet with them below. They looked at our food stores, noted that they were happy that our meat was from the US (Doug was careful not to show them the frozen duck breast from Martinique!) then they asked for a tip. Again, Doug declined, and they were OK with that too. It was an hour since we pulled into customs, and while not as easy as entering the French islands, it was much easier than expected.

After taking a nap and washing up, we headed out to change money. US credit cards can’t be used in Cuba – the US won’t allow it as part of the embargo. We were going to be all cash for the next 2 weeks and we couldn’t do anything that cost money until we exchanged money. As retaliation for the embargo, Cuba levies a 10% penalty on the US dollar. We knew this and had gotten enough Euros from ATM machines in Guadeloupe and Martinique to get us through Cuba.
We walked to the hotel at the marina where they exchange money. We asked at the desk and the woman made a few calls, then said no, they wouldn’t change money for us. Why? Who knows. Although we learned as we spent more time in Cuba, that sometimes things just don’t happen – sites are closed, events are cancelled, etc. It’s how it is.
We walked to the marina office to see if they could help. We asked the woman in uniform and she said she would see. She made a few calls and it didn’t look positive. Then she spoke to another woman in the office. This woman was not in uniform and appeared to just be hanging around/visiting (there’s a lot of that in Cuba). The second woman started talking loudly in Spanish and stormed out. We thought she was mad. Yikes! Despite our warm welcome and relatively easy check-in, we hadn’t totally shaken our “Cuba is scary” stereotype. We got up to leave. But the uniformed woman told us to wait. We had no idea what was going on. Then in walked a guy in street clothes with a ton of cash in a ziplock bag. No way! He was very nice and spoke a bit of English. He led us to an empty desk in the corner and said he would only change US$. We mostly had Euros, but we exchanged the US$ we had. And now we had another lesson on Cuba.
From the office, we walked to the marina bar next door. Some of the marina staff who had helped us tie up were there drinking and hanging out, but no one was behind the bar or appeared to work there. We grabbed two Cristal beers out of the fridge, walked to the register at the bar and waited, confused. Eventually one of the marina guys stepped behind the bar and took our $3 CUC for the 2 beers. Did the money go in his pocket or to the bar? Not sure, but we were happy.
We sat at one of a few tables outside overlooking a canal. There was a table of sailors littered with empty beer cans and cigarettes, and a table of locals with a big bottle of rum. We spoke to the sailors, an international group of salty guys including a guy with a tattoo all over his neck who ended up in Cuba after he broke his forestay (cable holding up his mast) while single handing his boat from Panama to Europe. We wondered if the locals would finish the bottle of rum and later that night saw that yes, they had finished it and were happily partying and dancing late into the night.
Heading South
Our first excursion was a 145-mile drive to Cienfuegos, a city of 150,000 people on Cuba’s southern coast. Our taxi driver Rigo picked us up in a refurbished 1956 Ford. Very cool looking, but we quickly realized that cars weren’t quite as comfortable in 1956 as they are today!

We got our first glimpses of Havana as we drove away from the marina, but the landscape quickly changed from city to farmland. The highway was large with 6 – 8 lanes, but few cars. As we passed near towns we shared the highway with people walking or riding bikes, and horses pulling all types of buggies and wagons.
As we drove, we were routinely reminded that Cuba isn’t like other places we’ve visited. Periodically, traffic would slow down and folks with guns in military uniform would be standing along the road watching the cars drive by. We were never stopped, but it was a little eerie. We also passed a number of patriotic billboards and sayings – “Viva the revolution!”, pictures of Che, quotes from Fidel, etc.

We met our local tour guide in Cienfuegos who walked us around the town. Cienfuegos was originally settled by the French and maintains some of its French roots. We walked around the central square and learned about Jose Marti, a hero from the Cuban War of Independence with Spain (Spanish American War to us). We had never heard of Marti, but his statues are everywhere in Cuba – in town squares, the Museum of the Revolution, and even just in yards along the road. We’ve since learned that Marti was a hero to Fidel and the other leaders of the revolution and his prominence grew following the revolution .

We learned that the beautiful houses around the town square and along the water had been owned by wealthy families prior to the revolution. Many are now government buildings or separated into very small apartments. Some of the government buildings and museums are well maintained, but others are in disrepair. Many of the houses converted to apartment buildings are crumbling.

We also learned that many engineers and other educated people quit their professional jobs to be waiters or waitresses because government pay is so low. We read that the average teacher in Cuba makes the equivalent of $20 per month. With tips, waitstaff in a tourist restaurant can make more than that in a day. We were told that Cienfuegos is hurting as young people leave for economic reasons. Many would like to move to the US, but that’s very hard now. So they mainly emigrate to Latin America or move to Havana.
We ended our afternoon in Cienfuegos at a great restaurant on the water, and a good example of the many private restaurant/hostels catering to tourists in Cuba (www.villalagarto.com). We ate upstairs in a treehouse like setting along the Bay. It was a great meal with a complimentary shot of banana rum after our meal.
From Cienfuegos we drove about 50 miles east to Trinidad, a smaller, but very historic city of about 75,000 people. Rigo dropped us off at the house where we were staying for the night (hostalyixi.jimdo.com). A nice 3-bedroom “Casa Particular” (private home similar to a B & B) near the town square. As an aside, for those of you who know Doug, he is an amazing travel planner and does extensive research on places we stay, reading reviews and looking at pictures. In this case, our entire Cienfuegos/Trinidad trip was organized by a Cuban tour organizer we learned about through friends. She arranged the entire trip – driver, guides, restaurants, and the Casa Particular. We didn’t know anything about the house before we arrived. Doug had mixed feelings. On one hand he was unsettled not having done his own research. On the other hand, it was nice to just show up. And even nicer to show up and have the owner of the house offer us watermelon juice with a shot of rum as a welcome!

We also met our excellent Trinidad tour guide, Little Man (we can’t remember his nickname in Spanish, but it means Little Man!). He took us on what was supposed to be an hour walking tour of the city, but ended up being more like two hours of both a walking tour and history lesson. Little Man was passionate about Cuba and loved sharing his knowledge. We learned about the Spanish architecture in the city and how to identify in what century a structure was built by the architecture.

Even better, was when Doug asked him a question about the revolution. It was clear that we didn’t know much. So he sat us down on a stoop and gave us an impassioned lesson. We learned about Batista and how he was first elected Cuban president and was an idealistic leader. After his presidential term he moved to Florida, returning to run again 8 years later. It looked like he was going to lose, so he led a coup and became a repressive military dictator, backed by the US. During his reign, the gap between rich and poor widened and stoked public sentiment for the revolution.
Little Man was full of stories of the revolution and Fidel’s glory – how great a student Fidel was, how he cheated death many times, how brave he was, etc. The lesson skipped the nastiness post-revolution and only touched on the Special Period. But he noted that the Cuban government was now at a turning point where they need to find the right balance between supporting people like him who are starting and running a private business, while not going back to the income inequality pre-revolution. While we put his enthusiasm for the revolution in context, it was interesting to hear such an idealistic rendition of history and national pride.

In addition to its history and architecture, Trinidad is known for its music. For dinner we went to Taberna La Botija, a restaurant that had a great rock/jazz quartet playing. The restaurant was a mix of locals and tourists. And again, we were offered a shot of rum after the meal.

We woke up in the morning at our Casa Particular to the smell of coffee and cooking and had a huge breakfast. Rigo picked us up at 8:30 as the town was starting its day. The roads were full of people, motorcycles, cars, bikes, and horse and buggy. But it wasn’t the heads down rat race to get to work and school we’re used to. Everyone was out, but they were talking, laughing and just hanging around.
Our first stop was the Manaca-Iznaga Tower. At the time, we didn’t know what the tower was given our language gap with Rigo. We looked it up later and found out it was a tower to watch over the valley, look for runaway slaves, and the bell singled the start and end of work for slaves in the valley – the largest sugar producing area at the turn of the century.
Rigo dropped us off at the little town by the tower and pointed us in the right direction. There was a school group of teenagers in front of us. So we followed them along a dirt road lined on both sides by vendors, mostly selling embroidery work on clothes or table linens. When we reached the tower, a sign stated that the entry fee for Cubans was 10 cents, foreigners $2. Funny! We paid our $8 and enjoyed a beautiful view of the valley.


Next, we drove about two hours to Santa Clara on narrow, two lane roads. We passed lush, rural land and through small towns clogged with bikes, motorcycles, people walking and a ton of horses. My favorite site was four people riding in a small buggy behind a horse, carefully balancing two big decorated cakes!
The last battle of the revolution was fought and won in Santa Clara, and it’s the home of the Che Guevara monument, museum and memorial. As we walked up to the huge monument, we noticed a number of men in military uniform and guns out. No messing around here! The monument was impressive, but the museum underneath was underwhelming. It was a small mish-mash of pictures of Che, Fidel and Raoul, guns used by the revolutionaries and odd other pieces – a pen, musical instruments, etc. There were small captions by each item, but no narrative or history. As we walked through the museum, a museum employee approached us, and in a serious tone, asked where we from. After we told her, she nodded and walked away. She didn’t ask that of anyone else. Hmmm.

The last thing we visited was the memorial room. Our family couldn’t agree if it was weird or cool. It was a hushed and dimly lit room. There were bronze plaques of the faces of all the leaders of the revolution on the wall, with one carnation next to each. The plaque for Che was larger and set off by itself with two carnations. There was also an eternal flame and little indoor garden with water trickling in one corner of the room. The room was patrolled by military guys with guns and ladies in museum uniforms walked around giving everyone the hairy eyeball. They were none too happy when Andy walked a little too close to the trickling water!
It poured rain on our drive back to Havana. There was lots of flooding along the way and we saw a number of cars dead on the road and a tractor trailer skidded off the road. And all those people/horses/bikes we saw along the highway yesterday? They were hanging out under overpasses waiting for the rain to end! Happily, the rain stopped as we got to the marina and we had a great sunset view.

A Few Down Days
We spent the next few days chilling out in and around Marina Hemingway, doing chores and soaking in the Cuban culture in a more relaxed way.
One of the first things we did was buy internet cards as we hadn’t had internet access since we left Key West. Internet is restricted in Cuba and only available via a WiFi connection, not directly via cellular – and only with an internet card that gives you time-bound access. You can buy internet cards from a government telecom office for $1 CUC (~ $1 US) for an hour of access, but the lines at the offices are long. If you’re willing to pay more, some businesses resell them. At Marina Hemingway, the Chinese Restaurant at the marina (yup, a Chinese Restaurant, surprising, but the food was pretty good) sold hour long cards for $1.50 CUC. Not a big deal for us, but a bummer for a Cuban teacher making $20 CUC per month.
One of our down days had me back up this mast. This time to change out a broken lightbulb in the tricolor fixture at the top of the mast. At night, each type of boat/situation has a specific set of lights that let other boats know who/what they are in the dark. For example, a sailboat under sail has green light shining to the right, red light shining to the left, and white light to the back. A sailboat under power has all those same lights, plus another white light visible from the right, left, and front, but not backwards. Our tricolor is at the top of the mast and shines the red/green/white under sail combination. Unfortunately, during our overnight to Cuba, the light in the tricolor burnt out, so back up the mast I went. It’s much easier to go up the mast in a marina vs. underway since there aren’t wind and waves, but it’s a far cry from changing a lightbulb in a land home.
Erin was excited to make a friend on another boat in the marina. Nina was another boat kid best described as a child of the world – born in the US to a South African father and Brazilian mother who has mostly lived in the US and is now headed off to sea for a few years. The two girls were happy to be off on their own, going to lunch, hanging at the bar/snack bar watching music videos and one day, staging a photo shoot around the marina.

We spent another day checking out the nearby town of Jaimanitas, home of Fusterlandia. José Rodríguez Fuster is a famous Cuban artist who in recent years has brought his work home in the form of a public art display throughout his hometown. Many homes in Jaimanitas are decorated with his whimsical tile-work and visitors can walk around a building and grounds covered in his work in the middle of town.

We were lucky enough to be at Marina Hemingway during their big fishing tournament – The Hemingway International Billfishing Tournament. The marina was decked out with a blow up arch, flags, and a stage. We watched boats come in throughout the day and spent a fun evening having mojitos outside, watching the scene. There was a dancing girl in traditional dress, dignitaries, and fishing teams in matching shirts sizing up the competition. I liked a Mexican team with their bright shirts and confident swagger. Doug liked a US team with one guy with a beer belly and a number of women in short shorts.

For our last non-tour evening, we headed to a club that plays classic rock every Sunday night. We walked to the marina road looking for a cab and found three parked together in the parking lot. We went over, and the drivers said no, they weren’t taking rides this evening. Next, we found one of the marina employees walking around the parking lot. He called a few guys with cabs. It wasn’t until the third call that he found someone willing to pick us up.
Rene picked us up in his semi-restored 50’s US car to take us to the show. Unfortunately, when we arrived the place was closed. We are learning, that’s how Cuba is sometimes. Rene saved the evening by turning up his radio thumping music and taking us to El Tablazo, a fun restaurant along the Malacon (seawall that runs along the north side of Havana). We were the only tourists there and it was fun joining the local scene. Cubans are boisterous with lots of laughing and fun!
Next up, Exploring the Real Cuba – Part 2, covering our time in Havana and Viñales. And then a Cuba photo reel by Erin.
I really, really enjoyed this – felt like I was there with you.
Glad you enjoyed it! Cuba was amazing.
Terrific. What a wonderful experience to give your children. Well done. Safe travels
Thanks Jack. Cuba was a great learning experience for the kids on many fronts.
What a colorful experience. Really enjoyed reading this, thank you! Hope you are doing great 🙂
Glad you enjoyed it and I hope all is well with you too!
Very nice story kid. Who knew all that? Almost as good as being there. Looking forward to part two. Dad
Love hearing your tales! So fun and informative!
Cheers.
Casey
Do you have a Youtube channel as well with this kind of content on it? I would love to see this post turned into a longer video if possible. Maybe I can share on it on my website.