On being tourists in Cuba

Start at the beginning of our trip to Cuba. We've also compiled all our Havana recommendations into a printable map and guide.

I often wonder why certain trips turn out better than others. Why was traveling through Oregon on the motorcycle such a magical experience? Why was our trip to Mexico somewhat lackluster in comparison? What did we do differently? What should we adjust for future trips?

Planning our Cuba trip felt like a particularly high-stakes proposition. I had dreamed of going to Cuba for years, piling another layer of expectation onto the task. And Cuba is unquestionably on the cusp of huge change, so while we can return to Cuba in the future, we’ll never again see the Cuba of today, defined in large part by more than five decades of Castro brothers' rule and the U.S. embargo.

One of the first decisions we made was to stay in Havana for most of our trip. Our logic: We cared more about experiencing Cuban life and culture than about seeing all the sights. But when we talked to others who had visited Cuba, they vigorously questioned this decision. Havana is dirty and full of tourists, they said. Viñales is magical. Trinidad is a beautiful colonial town. We struggled with how much weight to give their opinions (the most common first-timer trip to Cuba is an eight-day journey to Havana, Viñales, Cienfuegos and Trinidad).

As with our Oregon trip, this was a case where we felt like we got it exactly right. If we had to do the trip all over again, there’s very little I would change. So why did we have such a great time?

• If anything, we set our expectations too low. We expected the food to be bad, the streets to be dirty and filled to the brim with tourists. Knowing that I wouldn’t be happy with a diet of rice and beans, I spent a lot of time researching where I wanted to eat, and we ended up eating really well. Expectation successfully exceeded. Were the streets full of tourists? Yes in Habana Vieja, where we stayed for the first three nights. No in Habana Central, where we stayed for the next four. But Cubans live and work in even the most touristy areas. Habana Vieja was hardly a sanitized tourist zone.

• We were admittedly nervous about how well our Spanish would hold up after three years of neglect. And the first day in Cancun, I could barely form my mouth into Spanish words. But I could understand much of what was said to us, and by the last days of the trip, we were successfully chattering in Spanish. And this is one of my favorite parts of traveling in Latin America — our Spanish is good enough that we don’t feel constantly stymied by a language barrier. We don’t feel like every conversation is transactional (which is easy when consistently ordering things, buying things, arranging things, etc). And I think this was also one of the biggest differences between us and other tourists. Obviously plenty of Americans and Europeans speak Spanish, but plenty don’t. I had to translate for an American guy in our casa as he tried to arrange a 5am taxi pickup. Even though plenty of people in Havana spoke English, we would have felt so much more detached from the place if we hadn’t spoken Spanish.

• One consequence of living in Argentina is that we’re intimately familiar with what it’s like to live in Latin America. If someone in an official-ish capacity in the U.S. tells you that something isn’t possible, there’s a good chance that asking five more people isn’t going to change the answer. In Cuba (or Argentina), if someone tells you something’s not possible, go ask someone else. We met some other tourists who were frustrated by the fact that they didn’t have a working phone to make restaurant reservations. Get a phone card, we said. Tourists aren’t allowed to buy phone cards, they said. At which point, we burnished the phone card we had successfully purchased (we shared the code with them). Had we been denied a phone card at one store, we would have known to simply go to another.

• Even though tourism to Cuba is growing rapidly, the number of Americans who have gone independently is still comparatively low. By law, U.S. citizens are not allowed to go to Cuba simply as “tourists” (i.e., no sitting on the beach) and up until earlier this month, any Americans on a “cultural” trip had to go as part of an approved tour group. We didn’t want to go as part of a tour, and hence we knew that all the planning would fall to us. By contrast, many other tourists were at the mercy of their tour guide. We talked to one couple who said their guide “didn’t know what to do with them” while Obama was in town. That sort of follow-the-leader tourism isn’t for us, and we were glad we got to carve out our own trip.

• I’ve been making a conscious effort to slow down when we travel. On our first big trip together, we visited five countries in 17 days. Granted, we had a fantastic/amazing/unbeatable time, but some of my best memories from that trip were long nights sipping sangria in Barcelona, or lazy mornings in our hotel room. We could have skipped an entire destination (Prague, clearly) and still had a great trip. Now as I plan a trip, I try to focus on the overall experience and not worry about whether I’ve squished in every little sight (we didn’t see the Museumsinsel in Berlin, but, honestly, I’m fine with that). The downside is that if we don’t like a place, it can feel like we’re there for too long. But the upside is that if we do like a place — like Havana! — we really have a chance to soak it in. Most travelers we met spent between two and four days in Havana, and after hearing their impressions, I’m glad that we spent longer. If we had only stayed in Havana for two days, we easily would have been overwhelmed by the tourists and jingueros. But once we settled in, we were able to get past a lot of that and out into the less-touristy areas of the city.

• And finally, we’re not naive. We met one American tourist who had no idea that Obama was arriving in the Cuba the same day as she was. We listened to another American tourist rant about the fact that she had paid $5 to a ride a public bus that only costs a few cents. I could only shake my head at some of these people and wonder, “How did you end up in Cuba?”

- Steph