When I told people I was going to Cuba, a surprising number of them replied, “Oh, I was there years ago,” or, “A friend of mine just went there and loved it.” With restrictions on travel to Cuba for U.S. citizens becoming increasingly relaxed, now is a good time to see the country before it’s flooded with us.
That’s why my friend and fellow Phoenicia resident Lynn Davidson wanted to go, and she invited me along for company. Our plan was to straddle Christmas and New Year’s with ten days in Cuba, followed by three days in Mexico City, since we would fly by way of Mexico. Since the holiday season would be busy, we made our reservations three months in advance.
For many years, it was tricky for U.S. citizens to visit Cuba legally. (South of the U.S., we aren’t called “Americans,” since all of Latin America is considered part of “America.” People from north of the border are “norteamericanos.”) Until December 2014, when President Obama and Cuban leader Raúl Castro (Fidel’s brother) announced the opening up of relations between the two countries, legal travel required applying to the U.S. government for a license to go to Cuba. Applicants had to document one of twelve possible purposes, such as education, performance, import/export, visit to relatives. The application process was arduous, but it was easy to obtain a license through group travel, which was expensive but, nominally at least, tied to one of the specified purposes.
However, many North Americans, upon entering Cuba through a third country, avoided having their passports stamped by cooperative Cuban customs officials, and therefore were not subject to prosecution when returning to the U.S. Even before the opening of relations, it was common for U.S. customs to ignore the occasional Cuban stamp. A few stories circulated of massive fines levied on people illegally returning from Cuba, but those examples were rare.
Beginning last year, travelers who fit into any of the twelve legal categories are automatically granted a general license to visit Cuba, with no application required. One of the categories is journalism, so I figured I was covered. My traveling companion could, perhaps, qualify as my research assistant.
In September, when Lynn and I booked our tickets, we could not find any flights going from New York to Havana. (Later, I heard direct flights had been instituted, and just now I found a booking on Cayman Airlines, from JFK to Havana with a two-hour stopover at the Cayman Islands.) We ended up flying from Albany to Mexico City (by way of Charlotte, North Carolina) and leaving the following morning on Cubana airline for Havana. We could also have flown through Toronto, Montreal, or Cancún.
When I entered our passport information online for the Mexico-to-Havana flight, I was asked if we were going to Cuba legally, so of course, I checked “yes.” Then I checked “journalism” as my purpose. (A friend said she was not required to answer these questions when she made her plane reservation last March.) It turned out our Cuba travel guide (published by Moon in March 2015) indicated that foreign journalists are regarded with suspicion in Cuba and are followed around — just one of many statements from the book that proved to be incorrect. But I awoke several mornings at 3 a.m., wondering if I would end up in a Cuban jail.
Next we booked our lodging. In the good old days, I always traveled by whim, deciding my itinerary day by day, finding a hotel room when I hit town — but now we had only two weeks, and they were the busiest weeks of the year. The friend who had visited Cuba in March gave us the email address of a casa particular in Havana. As Ana Perera, the owner, later explained to us, the government began to allow people to rent out rooms in their homes during the Special Period of the 1990s, when the fall of the Soviet Union deprived Cuba of many trade resources. With income slowed to a trickle, Ana turned her home into a casa particular. It was illegal for private citizens to possess foreign currency, so she asked her guests to go to government-owned shops and buy food for her family in lieu of paying rent.
Although Internet is sparse and expensive in Cuba, many owners of these casas can now afford to communicate by email in order to book clients. Ana answered our email promptly, reserving a room for us for three nights at $35 per night. She also referred us to a casa owner in Trinidad de Cuba, a small city southeast of Havana, where we planned to stay for a week, and we soon had a room booked there for $25 per night. (Actually these prices were in Cuban convertible pesos, or CUC, pronounced “kook,” the parallel currency used by foreigners, with one CUC equivalent to roughly one U.S. dollar, although the CUC had gone down to 87 cents by the time we arrived. National pesos are valued at 25 pesos per CUC, and we occasionally saw signs in this currency but never actually handled it.)
Airbnb has been active in Cuba since last April, and we did try to book a room through the website for one night near the airport on our way back to Mexico City. The booking failed because of that same questionnaire about legality that had appeared with the flight reservation, except that this time, Lynn also had to answer the questions. For some reason, her answer was not received by Airbnb, and the booking was canceled, with repeat reservation blocked.
But like most problems in Cuba, there was a workaround. I had a long conversation with the proprietress in Spanish over the Airbnb message system, and she agreed to reserve a $25 room and send me a letter with her address and contact information so we could get in touch upon our arrival. The letter arrived a week later with a Miami postmark — a traveling friend had mailed it for her. All mail service between Cuba and the U.S. has been going through a third country, taking about three weeks, but recently both countries announced a pilot program of direct postal service, part of the general loosening up of relations.
Airbnb came through instantly for our three nights in Mexico City, and then we were all booked. Language came next. I already knew a little Spanish, but I wanted to be able to converse, so I listened to lesson tapes in my car every day for three and a half months. I recommend the Pimsleur system, supplemented by the free Internet site Duolingo.com, for enjoyable learning and well-scheduled reinforcement. A few times, I provided lunch for Spanish-speaking friends who helped me practice.
The travel guide suggested that we could live in Cuba on $30 to $60 a day, depending on our extravagance. I brought $700 for the ten days, in cash, since U.S. credit and debit cards do not yet work in Cuba. Lynn had to lend me a few bucks at the end, but another error from the guide was that we would have to pay a $25 exit fee.
With so much misinformation available, we were grateful that we could rely on the casa owners for help negotiating our stay. They arranged taxis, told us how much the fares would be, explained where to change money, and offered reasonably priced meals cooked by their employees, especially helpful in Havana, where we were staying in a residential neighborhood with almost no restaurants. The few we saw were holes in the wall, usually devoted to a single dish — pizza or chicken.
Ana spoke excellent English, but Alexis, our Trinidad casa owner, did not. He and his employee, Rosa, had just enough words to get by, so it was really helpful to know some Spanish, as fluent English is not widespread, even in the tourist industry.
Havana is huge, and in three days, we toured only a few areas, including Calle Obispo, the glitzy main drag of Old Havana, where massive colonial buildings, restored to elegance, and restaurants with live music give tourists chances to take photos and spend money. A block from Obispo are the tired streets that are more typical of Havana, which made me think of a frowsy middle-aged woman who lounges around in a plush but tattered robe, hair frizzed out, eyes bleary, yet with a grace that makes you always conscious of her faded beauty.
On many streets, drivers zigzag around giant potholes or piles of construction debris, while crumbling sidewalks present constant peril to pedestrians. Maybe five percent of the buildings glow with fresh coats of brilliant paint — royal blue, sea green, sandy yellow, warm pink — and sport balconies with curvy white pillars. The vast majority of houses are a muddy, mottled tan, with courtyard walls cobbled together from tin sheets and wire fencing, doors sagging on their hinges, broken chairs out front under scrubby trees.
The temperature, up in the 80s by midday, was unseasonably hot for December, according to residents. In the cool of the evening, I paced the streets near our casa, watching people mingle and lounge on the sidewalks. Kids played stickball in the street in front of a high-rise apartment building, and two boys bounced around on car tires. In a small park, a pair of girls hunched over a computer tablet. Timba music — the Cuban version of salsa — boomed through doorways. No one spoke to me as I walked, soaking up the vitality that shone through the decay.
In contrast, Trinidad, a 500-year-old hill town near the southern coast, is considerably more tidy. Magnificent colonial buildings hold sway around the historic Plaza Mayor, but even outside the tourist district, many of the houses have been spruced up. Tall windows with metal grilles face the street and often stand open so cooling breezes can pass through the houses. As we walked by in the evenings, we peeked through the grilles into living rooms where people sat talking or watching TV, sometimes in heavy dark wooden chairs beside lace-covered tables.
The sidewalks in Trinidad are only about three feet wide, forcing pedestrians to constantly step back and forth between the sidewalk and the street to make way for oncoming passersby, bicycles, cars, horse-drawn carts, bicycle taxis, and the occasional cowboy on horseback.
For the tourist, Trinidad has about a day’s worth of landmarks, museums, souvenir shops, and art galleries. A second day can be filled by a horseback ride into the nearby mountains and a trip to the beach at Ancon, where the silty water and wimpy waves are much inferior to the bracing surf at Amagansett. We watched a series of guests leave after spending two days at our casa, and I wondered why we had booked ourselves in for a week. By the end of our stay, I knew why — because we had taken the time to get to know the industrious Rosa, who after cooking and cleaning for us and struggling to understand our wants, invited us to her house for New Year’s Eve.
We walked the two blocks to her spartan little home, the two front rooms each lit by a single fluorescent tube, the dining room dominated by a framed poster of flowers, cake, and wine, in faded blue. For hours, relatives streamed in and out of the house, each new arrival delivering a kiss to everyone’s cheek, including those of the norteamericanas, although we never learned most of their names. One exception was a ten-year-old whose name I couldn’t pronounce until she wrote it out in my notebook: Leidydiana. I stared at the carefully formed script. “Lady Diana?” I asked. “La princesa de Inglaterra?” Her mother smiled, delighted that I knew her child’s namesake. The girl’s nickname is Leidy.
Rosa showed us a photo album from her daughter’s quinceañera, the grand party given for Latin American girls when they turn 15. A couple dozen studio photos showed the teenager in movie star poses, hair styled, in full make-up, wearing a series of ball gowns of various time periods, from the colonial era to the present.
We drank red wine and ate from a table laden with pork, salad, rice mixed with beans, flan. Sadly, Lynn and I ran out of steam by ten o’clock and went back to our casa to sleep, missing the midnight conga line that marked the turning of the year. But the warmth of Rosa and her family were the high point of our stay in Trinidad. I felt bad when she had to return, hung over, on New Year’s morning, to make us breakfast before our departure.
The restrictions on traveling to Cuba come from the U.S. government, not the Cubans, who have always welcomed tourists from around the world. (We met lots of Europeans there, and Ana said there have been many more Americans visiting over the past year.) As we prepared to fly home, I realized that on previous trips, U.S. customs officials had always asked me what countries I had visited. I certainly wasn’t going to lie about having gone to Cuba, since I was legal, with a press pass and a letter from my editor to prove my status as a journalist. But what about Lynn, who was perhaps not quite so legal?
I spent much of the flight from Mexico City to Dallas worrying maybe I ought to lie on her behalf and pretend we had spent two weeks in Mexico, hoping our passport stamps would be overlooked. But then if they noticed my Cuban exit stamp, could I go to jail?
In Dallas, we were directed to computer kiosks that scanned the ID page of each passport and took photos of us that were printed out on a scrap of paper. Customs officials compared the printouts with our passport photos, glanced in our faces, and waved us through without checking our passport stamps or asking us a single question. We were giddy with relief.
Maybe smaller airports have more personalized customs procedures, but it doesn’t appear that the government is too concerned about U.S. citizens visiting Cuba. One thing is for sure — whether relations between our countries keep improving or a new Republican president reverses the trend, changes will continue to happen, month by month. My advice to those thinking to visit Cuba this year: plunge in and don’t worry. Your casa owner will take care of you. And learn some Spanish. Conversing with Cubans was the best part of the trip.
Join the family! 
