For many travelers, the goal is to physically move - to be flung through airspace and to cross borders - but to remain in spaces that are comfortably familiar. They would prefer to speak English and to use U.S. currency and to avoid, except for those incidental times when fetching a drink or a towel, any contact with the locals.
Many others crave the opposite - not so much a vacation but an immersive experience, sharing the food, sharing language and picking up on the tiny details that shape daily life. Whether or not you desire it, this is the kind of experience the average traveler is likely to have in Cuba, because it is practically mandated by law.
The law - while relaxed - still puts strict limitations on what Americans can do when traveling to Cuba, requiring cultural exchange activities for many travelers. Some travel operators have interpreted the rules to mean that all-inclusive resorts - those booze-soaked cocoons popular in the Yucatan and elsewhere in the Caribbean - are off-limits to Americans (though they do exist). The travel restrictions and U.S. embargo - which will remain in effect until it is lifted by Congress - means travel to Cuba is not easily planned on a whim.
But it is well worth the legwork. Cuba had long been a place of distant fascination for me. When President Barack Obama announced that he would reopen diplomatic relations with the island nation, the urgency to go grew. (I spoke to many travelers who felt the same way, fearful that U.S. tourists would spoil the island.)
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Despite numerous novice traveler mishaps, Cuba ended up delivering on its magic. To see the island now is to see a place in flux, to play witness to history and to get a glimpse into the Cuban people’s mix of emotions - anxiety, excitement, fear - over the coming shift. It is to observe mind-bending surreality, to see hints of modernity - such as the crowds of tourists and locals slumped over smartphones and huddled around public WiFi spots - amid noisy, rumbling decades-old cars, the omnipresent reminder of a nation slowed by the embargo.
Everyone I encountered had a view on how the island will change and whether it will be for good or for bad: my tour guide; the geographer and taxi driver who studied the world but had never left the island; the man who sold me ice cream; the former nurse who made my breakfast at a guest house in Old Havana; the doctors who ran a guest house and cooked us fish in Viñales; the young musician who boasted that Cuba was free of American-brand racism. And everyone was happy to share (in Spanish, mind you).
Every day was filled with spectacular sights and deep conversations. I sensed that I was seeing a place that could rapidly slip away.
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I realized that I must have sounded suspicious, speaking slowly in Spanish inflected with a distinctly American accent.
“I don’t have cash but I have money that I can transfer to you on the Internet. Do you know about PayPal?”
The woman on the other end of the line sounded puzzled. No, no PayPal.
I was in Havana, and due to some bad counsel at the currency exchange counter in Cancun, Mexico, (do not change your U.S. dollars to Canadian ones, or you will lose big) my friend and I were running low on cash. We could pay our room and board, yes, but it meant cheap sandwiches from the tiny corner shop down the street for the rest of the week. There was little hope of getting any more cash - the embargo, after all, makes it nearly impossible. Had we really gotten desperate, we could have had someone wire us money, but that would have taken time, and on vacation, time is a premium. In the end, it meant no souvenirs - save for a few copies of Granma, the official voice of the Communist Party of Cuba Central Committee - a lot of walking and sticking to activities that were cheap.
That is lesson No. 1 for tourists from the United States. Cuba is a cash economy, and not a cash economy in the way you may be accustomed to thinking of one. Americans are, for the most part, barred from accessing their bank accounts from this tropical island. And even if we were not, keep in mind that nearly everything in Cuba takes time, that lines - for fruit and bread rations, for WiFi cards and at banks - have become an essential part of Cuban life. Even though carrying cash feels disconcerting, it will save you time, headaches and possibly a night crashing on the streets of Havana. (Luckily, it did not come to this for me.)
When visitors arrive in Cuba, foreign coinage is exchanged into a special currency known as a CUC - a Cuban convertible peso. Travelers from the United States are levied an immediate 10 percent penalty, so some opt to exchange first to euros. But do the math before you go this route, keeping in mind that many banks levy their own fees for exchanging U.S. dollars into euros.
Americans wishing to visit the island now must fall into one of 12 categories and still should document their trips - keeping notes, itineraries and receipts. The most expansive of these categories - the one the casual traveler is most likely to qualify under - is people-to-people travel. And that, as its name suggests, requires getting away from a resort, out of the tour bus and interacting with Cubans. If this is your kind of vacation, Cuba is your ideal destination.
My friend and I booked a tour through Cuba Adventures, opting for its six-day Western Cuba tour package. We paid deposits with credit cards online (they have offices based outside of Cuba).
Official people-to-people tours tend to be pricier than ordinary ones and pack in a full day of educational activities while also arranging transportation, accommodations and meals in order to ensure compliance with U.S. laws.
While my tour was not officially licensed as a people-to-people one, it featured many of the aspects of such a tour: stays in guest houses, educational tours, lessons on history and politics (formal and informal, my favorite, perhaps, being the one from the geographer, who gave me a ride to the airport). But it had a much lighter schedule of activities, meaning more free time. In recent months, the Obama administration has expanded the category to allow ordinary travelers - rather than tour groups, which charge a premium - to plot their own people-to-people tours.
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My friend - a graduate student studying urban planning - and I began our journey in Cancun, where we purchased a Cuban visa ($25 to $30) and filled out a simple form given to us at the ticket counter specifying which of the 12 categories we were traveling to Cuba under. (I went as a journalist.) Our trip happened to coincide with Obama’s historic visit to the island, but we planned ours well in advance of the White House’s announcement.
While U.S. travelers have been flying to Havana for years from foreign locales - Costa Rica and Mexico are popular - commercial airlines will soon offer direct flights.
We landed at José Martí International Airport, gawking from the plane windows at an island bathed in spectacular shades of green. After a long wait in a currency line, we met our tour in Soroa, a mountainside resort, penetrating deep into the green and winding our way through a forest of astonishing density. The tour had arranged for a driver from the airport.
From the balcony of our guest house, my friend and I took in the views of a setting that was reminiscent of “Jurassic Park,” where the mysterious hoots of birds competed with the bass thump of party music in the distance.
Breakfast at our guest house - and nearly every day - would bring a rainbow’s array of tropical fruit, cheese, meats and bread. The following day, at Soroa’s orchid gardens, we saw otherworldly trees and flowers - clusters of roses that hung from trees in arrangements that resembled globes, trees anchored into cliffsides with tentacle-like roots. The garden sloped upwards, and on its peak we sipped freshly made fruit juices and listened to live music. Even I, someone who regularly manages to kill even the hardiest of succulents, found our very in-depth lecture about the endless variety of orchids fascinating.
Later, our tour bus rambled on to a waterfall beyond a short, easy hike, where my friend and I paddled around in the cool water among weary backpackers and hikers.
Our next stop was Viñales, a small city further inland. From the Hotel Los Jazmines, perched high above the valley, we surveyed a landscape unlike any I had ever seen, deeply verdant and dominated by mogotes, large, steep-sided hills that seem to appear from nowhere.
In this quiet town, we toured a tobacco farm and ate dinner at an organic farm high above the valley, where a cat threaded its way through our feet. An old man gave us a tour of the garden, showing us his handwritten notes that identified the specimens in Spanish, French and English.
The following day we headed to Havana, a city still gridlocked as President Obama touched down for a historic visit. In one of the narrow, aging buildings in Old Havana - where a shortage of construction supplies means the buildings show their age - my friend and I checked into a rooftop guest house, a sanctuary from the noise and the bustle below. From there, we could see the dense clusters of decaying buildings and the gleaming dome of the Capitol building in the distance.
That night, hours after Obama delivered an address to Cubans, I ordered an ice cream cone.
“American?” the server inquired in English. I nodded.
“Obama, your president,” he said.
“His words,” he said, giving a mock shiver and brushing his forearms, saying with his body language: gave me shivers.
He took the cone back from me and piled on another lump of soft serve.
The next day came a sobering tour of Old Havana, from its colonial roots to its modern turmoil. Our tour guide ended in a square where we gathered around a statue of a naked woman riding atop a chicken, tears running down her face while she holds an enormous fork.
It was an expression of the anguish of what was called the “Special Period,” when the dissolution of the Soviet Union devastated the Cuban economy, leading to widespread food shortages. As our tour guide tells it, women grew so desperate that they turned to prostitution for food.
For the remainder of our unguided trip, we strolled the Malecón - the seawall that separates the city from the crashing waves - and wandered the narrow, charming streets of Old Havana. In the mornings, we took long breakfasts with a former nurse who now served as house help and gave us a crash course on the state of Cuban politics.
We, in turn, quenched her curiosity about the United States, a place she knew mostly through movies and state television, where one channel seemed to play U.S. crime dramas exclusively. She asked us if all Texans carried guns on their belts, wore hats and talked strangely.
Cubans, she said, are ambivalent about the warming relations with the United States. A former hospital worker, she had seen the effects the embargo had on drug shortages. But she feared what more capitalism - and more tourists - would mean for the island.
On her recommendation, we took a group taxi to the beach town Guanabo, waiting in a line near the Capitol to ride with a group of young men in an old car. We dipped our toes in the powder-white sand and waded in the warm, Caribbean water before hitching a ride back.
On my final night, I tried out some establishments that seemed to represent where Old Havana is headed. The restaurant 304 O’Reilly served up small plates and Spanish-style tapas. Across the street, at El Del Frente, the walls were washed white with hip stencils of bicycles and its rooftop bar was strung with lights.
Blended cocktails were served in tall glasses with accoutrements meticulously arranged with tweezers. They seemed more fit for an art show than for consumption.
The bartender told me that model Naomi Campbell has dined there. On my first of two visits, a German television crew was filming some sort of fashion reality show. I scrimped to ensure I had enough for a nice meal on the final night - though this meant forgoing a taxi from a guest house more than a mile from Old Havana and taking a group taxi on the way home.
The bartender boasted that the tunes piped in through the speakers - unusual for Old Havana, where establishments more often have live music - was from a radio station in America. I told him the spot felt a little like South Beach, very “guay,” I said, employing the Castillian word for “cool.”
As the sun set over Old Havana, I watched a couple dance in the fading light, shimmying and swaying not to Cuban salsa music but to the strains of Justin Bieber, transmitted through the warm air all the way from New York City.
If you go
Where to stay
Guest houses, known as casa particulares, can now be booked through Airbnb on many parts of the island. The website casaparticular.com also has guest house listings with email addresses and phone numbers.
Where to eat
304 O’Reilly, Havana
Inventive small plates and Spanish-style tapas. Cocktails range from around $2 to $12 and small plates run from $2 to $14.
El Del Frente
303 O’Reilly, Havana
Beautiful cocktails and a gorgeous rooftop. Cocktails cost about $4.50.
Finca Agroecologica El Paraiso
Carretera Al Cementerio KM 1 1/2, Vinales
Tour the garden of this organic farm and eat a fantastic multi-course meal with a valley view.
What to do
Viñales bus tour
The main part of town is ringed with attractions: caves and underwater river tours, ancient art, vista points. The hop-on, hop-off bus tour allows you to see several in one day. Purchase the $5.50 ticket at a ticket office on Salvador Cisneros across the street from Viñales Plaza.
Hotel Nacional de Cuba
Calle Obispo Esquina A S/N, La Habana 10100
Perched atop a hill near the Malecón, this hotel has fantastic ocean views from its garden. It has played host to all kinds of dignitaries, including President Obama. Winston Churchill, Nat King Cole and Ernest Hemingway have also been guests. Wander the lobby, enjoy a drink on the back patio or take a guided tour.
Soroa Orchid Botanical Garden
At the end of a guided tour, you’ll be an expert on orchids. Atop the garden, enjoy fresh-squeezed juices and live music.
This sea wall runs nearly five miles and is great for an exhilarating ocean-side walk and people-watching. Start at Castillo de San Salvador de la Punta, at the intersection of Paseo de Martí and the Malecón.