Visiting Cuba is like going on a date with someone you met online. You’re enchanted by pictures of an attractive 20 year old, but when you arrive, they turn out to be 90. I’d never had an interest in visiting a place that people had described as impoverished, lacking in phone service and most of the western amenities I’ve grown accustomed to. Still, whenever you mention Cuba, people exclaim that they’ve always wanted to go. When I got an opportunity to get paid to go to Cuba, I decided to see for myself.

The trouble with Cuba is that most of what we know about it has been documented in professional photography. People told me they wanted to see the old cars, but once you get in one, you can see they’re being held together by duct tape, rubber bands, and rope. I heard of the beautiful architecture, but what you see is dilapidated skeletons collapsing in on themselves.

Cuba is indeed a museum of the past, but it’s a museum without a roof where everything has been exposed to the elements for the past 60 years. Despite all of this, we made the best of our visit and managed to see some of the unique things that make it a desirable destination.

Because visits to Cuba by Americans are restricted, we worked with a destination manager who’d claimed to have lots of experience leading tours of Cuba. While it did seem that she had many connections, it didn’t seem like she had any experience leading tours. One of our guests asked me why Joan and I were there since the destination manager, Trish, was leading the tour. I replied, “to make sure the interests of our clients are properly served”. By the end, it was apparent how important that role was.

Varadero

We began our trip in Varadero. The group that had visited the previous year lamented that they didn’t get any beach time. This disappointment was understandable since it would seem strange to come to the Caribbean in the midst of the Pacific Northwest winter and not enjoy some time in the sun. Unfortunately our two days at the resort were blemished with constant rain so it felt more like Oregon than we’d hoped.

I was a bit puzzled by the number of all inclusive destination resorts lining the beachfront. My understanding was that the country was impoverished, and I couldn’t help but note the irony of foreigners living exactly the way they had before the 1959 revolution. I wondered if this narrow island spit was another part of Cuba that had been carved out by some foreign power, as the US had done with Guantanamo bay. I asked our guide how this was possible, but she just explained that the resorts were owned by European companies and the Cuban government wanted the tourist dollars.

During the brief period that the sun came out, I saw the appeal of the clear blue waves crashing upon the fine white sand. The only disruption to the beach paradise was the constant sound of a whistle while the life guards directed people to come closer to the shore. Varadero is the northernmost point of Cuba, which also makes it the closest point to the United states. As a result, water moving between the Atlantic and the Caribbean is squeezed through the channel created by the two. Swimming too far from shore risks getting snatched out into the Florida current.

In the past, many wealthy foreigners built their homes out there, including Irénée du Pont. We got to visit Xanadu, the mansion he built that has since been converted to a restaurant and hotel. Eating dinner on the water was one of the most opulent experiences of my life, but when we got back from Cuba, I recommended that we put Varadero at the end of any future tours to Cuba as it made for a pretty big disconnect between the rest of what we were to see.

Havana

Havana is a series of circles that degrade as you get further from the center. The historic center is beautiful. Most of the buildings in the four square blocks beside the capital are in immaculate condition. This includes the former capital building which looks like it was finished yesterday, even though it hasn’t housed an elected body since 1959. Today it is a museum of Cuban history.

The blocks around the capitol feel very European with narrow cobblestone streets filled with shops and restaurants. Once you get outside of these blocks, you enter Old Town, which is much less cared for. It hosts some of the famous restaurants and bars frequented by people like Hemingway. We went to his favorite, El Floridita Bar, to listen to live music while sipping daiquiris.

Drinking is such a prominent past time in Cuba that they refer to rum as vitamin R. Three drinks were included at every meal, and it was up to you whether you had three cocktails or three glasses of water. I think I drank more that week than any other of my life!

Most of the restaurants where we ate were located in Old Town. They always included live music as well as a variety of foods to choose from. Pork and lobster were the most frequent offerings, and by the end of the week I was surprised to hear myself turn down one more serving of lobster.

Trish didn’t do much to coordinate the day to day experience, and we were always left wondering what was happening or what was being served. Sometimes we’d just walk in and sit down until food was placed in front of us. Other times we were asked, “chicken, fish, or pork” with no further description, as if being served on an airplane. While I tried to get her to give us more information, her lack of Spanish made it difficult. In the end, we had to embrace spontaneity.

Not only were the foods often a surprise, but so were the environments. At one place we were dining, some of the guests remarked that they thought something was leaking as they were getting small drops of water on them. When they asked the manager about it, she pointed two stories up and explained there was no roof. It was rain that was dripping on them. Because we’d come in at night, we hadn’t noticed the restaurant was open air.

Another time, we were well aware of what was in store. Trish had told us we would be eating on the rooftop of a hotel. We had to remind her several times that the winter storm that wreaked havoc on the east coast of the United States was now bringing strong winds and cold temperatures to Cuba. Not having an alternative she just said “dress warmly”, and I have a unique picture tourists wearing puffy coats in Cuba.

Her attention to our accommodations wasn’t much better. In an attempt to curry favor with a hotel she said she’d always wanted to bring a group to, she brought us to a place that was completely unrealistic for a group of seniors. Despite the group having loved the hotel they’d stayed in the previous year, Trish recommended that we stay at the Villa Vedado mansion. She’d sold it as an “authentic” experience, but I don’t know that authentic is what you want in an impoverished country. The converted mansion would have been charming for a young couple who didn’t have much money, but it was a complete failure for a group of retirees who had earned comforts after years of hard work.

The mansion was in the outer circle around Havana which meant there was nothing attractive around it. Trish had said that we could walk around the neighborhood visiting nearby shops. While I made an attempt to video document the neighborhood, Joan warned me about not having the camera too prevalent. Despite my efforts to greet people we passed, no one responded. This to me is a sign of a neighborhood you should not be in.

The mansion itself was like an impenetrable castle for our senior guests who had to climb two winding flights of stairs to get to the main level with the rooms. Once inside, nothing worked properly. Door locks were broken, toilets didn’t flush, AC units didn’t work. Again, these are all charms of traveling when you’re young but not what you expect when you’re in your seventies.

Within an hour, I was on the phone to my boss, and by the end of the evening, we were assured we would be switched to a new hotel the next day. When we arrived at the modern oceanfront hotel, we wondered how our host could have been unaware of the difference.

We felt a bit embarrassed loading our bags onto the bus just one morning after we had arrived, but it was so intolerable, we didn’t even want to bother returning. We headed straight off on our day before checking into the new hotel.

Our first stop was the Hemingway House, which probably had the highest concentration of white people in the island. The businesses at the property took advantage of this by overcharging for everything. I was shocked when they handed me a coffee in a clear plastic cup wrapped in a napkin and asked for $7! That’s probably the most I’ve ever paid for a coffee.

Throngs of tourists gathered around the house like ants around a discarded corn flake pressing their faces against the windows, trying to imagine Hemingway’s life there. Like people’s attraction to Cuba, I’ve never understood the draw to Hemingway. While he’s touted as a great writer, he was never considered a great man, except by himself. He was an alcoholic, a misogynist, and took his own life. It seems odd that so many would make a pilgrimage to see where he lived his self-centered life.

What we visited next couldn’t have been a greater contrast. In one of my favorite experiences in Cuba, we were taken outside the town to a decommissioned water tank. The surrounding community had come together to make it a cultural center. They tiled the outside and created workshops and stores in the surrounding buildings. Our host showed us a kiln where the tiles were fired after they were decorated by children.

We were led to the top, where there was a bar and a stage. The people performing possessed the best energy of any of the groups we witnessed while in Cuba. Whether inspired by their performance or the unique cocktail that they’d served, several of us even got up to dance.

On another day, our guests attended a performance by young local musicians which everyone also seemed to love. Unfortunately, I had to miss it as I had to escort one of the guests to the US embassy to get a passport replacement since she’d been deprived of it during a mugging after our arrival to Havana. This after being told just 15 minutes before how safe Havana was. On the plus side, I now know how to handle an emergency passport replacement.

There were a few other unique experiences that were included in our program, and while interesting, didn’t seem quite appropriate for our group. They were a farm visit, a cigar and rum tasting, and a fashion show.

The farm visit was very informative. The founder explained the challenges he experienced in digging a well and moving from city life to rural life. He showed us the variety of plants that supplied many of the restaurants in Havana and talked about his program that donated plant starts to new farmers. On our way back to the hotel, one of my guests raised her hand and asked me, “Now usually when you enter the US, aren’t you required to fill out a questionnaire that asks if you’ve visited a farm?” Trish told us not to worry about it.

That was often her answer to everything. While Joan had put together an information packet for the Cuba trip, Trish contradicted us from day one saying, “because I have Global Entry, they never check my bags”. I’m thinking, “does that not make it smuggling?” and recommended to the guests to use their common sense on what they brought back. I love my Global Entry more than I love rum and cigars!

I don’t think we had much to worry about. I’m not sure if our people were big consumers of either. On the day of our departure, Trish had scheduled a visit to a cigar bar. On our way in, the hosts handed out cigars and glasses of rum. They were a little surprised that so few of us took any. Perhaps it was because it was 9 in the morning.

Once inside, we listened to a woman extolling the virtues of cigar smoking as if we were watching a 1950s ad for Camel cigarettes. Unfortunately, she didn’t realize that we were from the west coast of the United States, a place that places value on a healthy lifestyle. She told us how cool it looked for women to smoke cigars, eliciting memories of friends trying to coax us into smoking when we were teenagers. Despite the pushing of the liquor and cigars, we enjoyed the entrepreneurialism of the women who ran the business from a beautifully preserved mansion, which brings me to our last event.

Trish was very excited to bring us to a fashion show which she shared would be attended by dignitaries and Cuba’s elite. It sounded intriguing, but in the itinerary she never mentioned needing formal wear. We did our best with what we had and headed off to an early dinner so we wouldn’t miss the show.

By this time I’d given up on trying to rope Trish into a time schedule, and when we were sitting at the restaurant beforehand, someone asked me if we should be leaving. I told them that Trish was in charge. When we did arrive, we were late which interrupted the gathering. Add to that we were inappropriately dressed for the occasion.

It didn’t matter too much as all eyes were on the models. I’ve never really understood fashion, at least the kind where people wear ostentatious outfits, where you’re left pondering, “when would one actually wear that outfit?” They paraded their wares with the blank faces of someone in a coma, and I struggled to be any more enthusiastic.

I thought of the poverty we’d waded through all week long. The event was completely out of sync with the country as well as our group. While it was unique, I think most of our people felt awkward. One person turned to me and commented, “Oh great; pretentious and crowded. My favorite.”

Trish was visibly disappointed when I told her the group was ready to leave, but I think at this point she’d given up on trying to impress me as well. I would have thought she’d noticed our people sitting bored while everyone else mingled, speaking in a language foreign to most of us. Not even one of our people slumped over sleeping seemed to catch her attention.

At this point I realized that Trish embodied the problem of the foreigner in Cuba. They are so wrapped up in enjoying their holiday, that they fail to notice the misery of those around them. I’m not sure I’d recommend a visit to Cuba unless you go for humanitarian reasons. While that was the purpose listed on our visa, I’m afraid we didn’t do much to improve their lives, though we do have a better understanding of the challenges they face.