Cuba for Independent-traveling Americans Easier Than Experts Letting On

Cuba for Independent-traveling Americans Easier Than Experts Letting On

Silhouetted by the sunrise, Dad gazes at Cuba from the top deck of our ship. Ninety percent of our trip was spent aboard.

My father and I traveled to Cuba from March 31 to April 7, 2017. We took our travel agent’s advice and booked a cruise which originated in Montego Bay, Jamaica, and circumnavigated the 780-mile-long island in eight days stopping at three ports. We spent about 90 percent of our time aboard ship, and since Cuba cannot accommodate larger vessels, that meant we sailed in an outdated Greek liner built in 1994. The most exciting part of the cruise was a glimpse at Guantanamo Bay Naval Base as the boat hugged the southeastern coast.

I began to suspect that the restrictive “for U.S. citizens only” tour that our Florida-based travel agent and a slew of other experts said was the only way for Americans to see Cuba was for suckers while at our first port-of-call. Ironically our ship pulled into Santiago de Cuba on April 1. I observed everything from the top deck, enjoying that new place buzz, as the sun broke above the horizon and burned off much of the orange smog. By 9:00 a.m. we were disembarking and setting foot on Cuban soil for the first time. But this would not be for long. Minutes after passing through the surprisingly relaxed and friendly customs, our group of Americans were horded onto buses. We wouldn’t feel the earth under our feet for another half hour.

Our first stop was a traditional dance recital set up in what used to be the backyard of a wealthy family before they fled the revolution. My attention, however, focused on what took place outside the iron post fence. Two police officers chatted under a mango tree. One of those iconic glossy 1950s American cars, a robin’s egg blue convertible, just passed. I had been in Cuba less than two hours, and already I grew antsy.

Fifteen minutes later, I watched from the air-conditioned coach people strolling the streets. Some stared back with envy too, but I suspected for different reasons. The local mode of transportation are open-air cattle-style buses, and the passengers are packed in with barely breathing room. Our Chinese-built Transtur even had a restroom.

The driver heroically steered along the windy roads to Castillo San Pedro de la Roca, a fortress built into the cliff face in the early 1600s to keep out pirates. The only way to hike to the top was through boisterous vendors selling wood carved model mid-century cars, “Cuba” license plates, Che Guevara t-shirts and pickaninnies. Which brings me to another misconception. We quickly figured out that the greenback is the preferred currency in Cuba, and legally. We lost 15 percent of our conversion due to the misleading information that we needed to change dollars for the convertible currency for tourists, also known as the CUC (pronounced “cook”). Even our guide, who had insisted we needed to swap our currency at the strangely convenient trailer next to the terminal before we could board his bus, requested U.S. dollars for tips.

The next “for Americans only” stop, San Juan Hill, was unexpectedly well-maintained. We Americans call it the Spanish-American war, for we helped secure Cuba’s independence from Spain in 1898. Our guide referred to it as the Cuban-American War. The following stopover was the bullet-riddled mustard yellow stucco Moncada Barracks, now a museum, site of what Cubans consider the first rebel push against the government. Standing before poster-sized photographs of decomposing bodies of defeated revolutionaries, our host emphasized the war against Batista was waged largely by machetes that slaves used in the sugar cane fields.

One of the “for Americans only” stopovers: a dance recital in Santiago de Cuba set up in the courtyard of a makeshift cultural center.

Back on the bus, I saw no visible tributes to Santiago de Cuba’s hometown prodigy Desi Arnaz Sr. from I Love Lucy fame, but stately statues and murals paying homage to Fidel, Che and Cuba’s “founding fathers” were everywhere. Our driver blasted past the Bacardi rum factory near the docks despite it being a scheduled final stop, one I was looking forward to. There wasn’t enough time, our guide explained. We had to embark on the ship by lunch to make the 3:00 p.m. sailing for Havana.

Dad napping in our ship’s cabin.

After two days at sea, during which time I had plenty of opportunity to regret our travel arrangements, we reached the capital city. This would be our only overnighter in port. Thank goodness we left the tour bus behind for the morning portion of our two-part excursion. Our hostess, a former school teacher who never allowed us to stray far, shepherded us through Old Havana, pointing out buildings and pushing the government dogma at every chance.

It was here in Cuba’s largest city that our journey took on new meaning—or at least gave my father and me an awakened catharsis. While passing down San Ignacio, we came across a high school baseball team from Colorado visiting on the same visa as we and most other Americans from our ship—the “education visa.” They told my dad and me they were staying at the Casa Particular Aurora, an emerging trend in privately owned guest houses open to foreigners, including Americans. It wasn’t ritzy, one boy said, but the owners had a friendly dog. Their rooms had air conditioning too. I figured that our stateside travel advisers and most of what I had researched on the internet exaggerated the difficulty of Americans staying in Cuban hotels. From half a block away our chaperone called for us to catch up to the group. I followed like a sixth-grader on a field trip, my frustrations mounting.

We lunched aboard ship, then an hour later climbed back on the same Transtur used in Santiago de Cuba. Our guide claimed the dilapidated buildings we passed along the Malecón highway were a result of hurricanes and the embargo. I noted a woman hauling two jugs of water up to her apartment in a building crumbling so badly the staircase was visible from the road. We sped by the new U.S. Embassy without comment from our guide. She did point out the Russian Embassy, one of the largest structures in Havana, shaped like a dagger stabbing the ground. Tributes to Che and Fidel were again all over, but many locals openly displayed the Stars and Stripes on t-shirts, shorts, handbags and the vintage American muscle cars that give Havana most of its color.

Dad and I: Watch out for the “kissing women” of Old Havana’s Plaza de San Francisco. They’ll plant a sticky kiss on your cheek before you know it, then demand $20 USD for a photo op.

We were let out to roam the massive parking lot of the Plaza de la Revolución where men in these spectacular vehicles provided short drives for a fee in front of dominating images of revolutionary heroes. The owners seemed as proud of their steel possessions as American teenagers 60 years ago must have been. My dad grew excited when he spotted his family’s car, a glossy pink 1957 Chevrolet Bel Air. I gazed around, and noticed the government buildings surrounding the square were the only ones nearby with air conditioning units jetting from the windows. Within a half hour, it was back on the Transtur. The day ended at an immense souvenir shack.

Revolution Plaza old cars
Images of revolutionary heroes look on as owners of iconic American muscle cars give tourists rides for a fee at Havana’s Plaza de la Revolución.

After returning to the ship, I sat in our two-bed cabin and pondered. I knew something was missing from our travel experience. Hearing from our non-American shipmates (Canadians and Germans, mostly) that they had entirely different land experiences than ours, like exploring waterfalls and visiting Hemingway’s Havana home, only fortified my desire to see more. Encouraged by the Colorado baseball team and the other Americans we had encountered who said they reserved lodgings on land without hassle, I decided to go exploring. With Dad choosing to remain behind, I at last hit the streets of Cuba unchaperoned.

I roamed aimlessly and yet purposefully. I went anywhere I wanted, and snapped photos of everything and anyone. I had been longing for a cold cerveza at Floridita (also known as Ernest Hemingway’s favorite cocktail bar) on Calle Obispo ever since we passed it that morning, but there were so many Cubans and tourists squeezed inside and on the patio, the place was bulging at the seams. So I kept moving. Most of the other establishments were packed too.

Apart from my stale tour group, I was often approached by residents who could tell I was from the United States. Sometimes they tried to sell me something, like a caricature portrait scribbled on a page from a notepad in under 30 seconds, but a gentle “no gracias” would turn into a congenial conversation. “Yo soy Cubano,” I would say for a show of mutual respect, eliciting chuckles at my attempts at Spanish.

Outside fancier hotels, locals and visitors sat on curbs, heads drooped and fingers working like spider legs over their cell phones. Hot spots in front of these places provided the only cell and internet access. I joined the flock, knees pulled to my chest, and caught up on my messages. Hungry for something sweet, I found the Café Bohemia free from crowds so I sat outside and ordered the chocolate and pear, unsure what it was. I was happy to see my server set before me a very dense-looking chocolate cake with dried pears dusted with powdered sugar fanned on top. It was quite tasty. And I was accompanied by my own mariachi band.

At 9:30 p.m. I returned to the ship, happy to have indulged in some free time in the city but hungry for more. I was angry with our stateside tour operator and myself for falling for his pitch. I can’t even recall what our teacher guide showed us the second day ashore. All I remember were long bus rides and a seaside neighborhood in which an artist covered many of the buildings in multicolored tiles. And of course there were plenty of shopping stops. I started to believe that our travel agency and the Cuban government had fashioned some kind of a financial deal.

The coach driver dropped us off dockside at noon. There was enough time for Dad and me to sightsee before our evening sailing. I relished the ease for us to go back and forth through customs, as if we were passing old friends. Again I delighted in being in the city unescorted. This time I led Dad around as if I knew the city firsthand.

Cuban in USA attire
A common scene: Locals boldly displaying the Stars and Stripes. This man is resting after a shopping spree in Cienfuegos.

Just when we were feeling like Habaneros, it was time to board ship for our last destination. As we pulled away from the small pier, I watched from the top deck people gather along the shoreline near the Malecón. With arms flapping above their heads, they shouted “Buen viaje!” Drivers in their flamboyant American cars honked from the highway and waved outside open windows. I felt a bit choked up and wished I could have stayed longer.

My first glimpse of Cienfuegos was two mornings later as the ship eased past a sign on the bay shore greeting seafarers with “Bienvenidos Socialista” (Welcome, Socialist). Closer to town, a more commercial center emerged in the blood-red of dawn. In this city of 150,000, the French-American origins were visible: New Orleans-style architecture and the few remaining French named streets. Cienfuegos also revealed what I thought the most contrasts of the two Cuban cities we’d seen. Poverty was everywhere, as was a rising consumerism. While mule-drawn carts were more common than automobiles, contemporary Japanese-built cars far outnumbered the American antiques that ruled Havana’s roadways. And while the bustling 10-block pedestrian street Avenida 54 showcased Western-style boutiques and shops, albeit without air conditioning and glam, the most common way of communicating were still through phone booths that dotted the avenue.

Cienfuegos Avenida 54
Even along the modern and bustling pedestrian street Avenida 54 in Cienfuegos, telephone booths are the norm in Cuba.

Our Cienfuegos guide was far less organized than our Havana schoolmarm, so while she ushered us down the teeming pathway my dad and I along with two shipmates took advantage by ditching the group. I had become spoiled wandering Havana unrestrained and wanted a taste for more. We grabbed a boxed lunch of the native favorite sold by street vendors, arroz con pollo (rice with chicken), for $5 USD and headed toward the Plaza de Armas where we knew our bus would be waiting. The scented smoke of roasting corn and tortillas from wood fires followed us along our walk while we munched.

A good reprieve from the blazing sun after our long hike was at the canopied Polinesio restaurant for a potent and refreshing mojito. Our server told us through halting English he had been waiting over a year for his travel visa so he could visit an uncle in Miami. As the locals say, “no problema,” and he laughed at the bureaucratic red tape. When I mentioned I’d like to buy the “Havana Club” glass I’d been drinking from for a souvenir, he happily handed me a clean tumbler free of charge. I left a few CUCs on the table for good measure.

An hour later our chaperone had gotten her head together and gathered her flock of wayward Americans for the bus ride back to the pier. By 8:00 p.m. the ship navigated away from the makeshift dock. Specks of light dotted the coastline and soon I couldn’t distinguish them from the stars that sugared the indigo sky. The aroma of wood burning fires grew fainter too.

Watching Cuba vanish into darkness, I wish I had spent more time on land. It was a learning experience in many ways. We needed the travel experts like Cuba needs another stucco building covered in bullet holes. For anyone aching to get a look at the real Cuba, obtain the proper visas, book your airline tickets (eight U.S. airlines currently fly into the country) and make reservations at a private- or government-owned lodging open for foreign tourists. Once inside on your own, you’ll discover Cuba isn’t called the Pearl of the Antilles for no reason. It’s a pearl encased in a barnacle-covered gnarly clamshell, but a fine nugget worth exploring apart from the contrived “Americans only” land tours nonetheless.

The sun sets over Cienfuegos Harbor as we sail for our disembarkation in Montego Bay.


U.S. Dept. of State
Visa fees
U.S. Embassy in Cuba
Moncada Barracks
8 U.S. airlines fly to Cuba
Cuba geography
Santiago de Cuba


Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Google+ photo

You are commenting using your Google+ account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )


Connecting to %s