Latin-Caribbean Travel

Should you travel to Cuba?

On Havana’s famous seaside promenade, the Malécon.
On Havana’s famous seaside promenade, the Malécon.

Editor’s note: Jane Wooldridge traveled to Cuba recently as a private citizen in compliance with rules published by the U.S. State Department in January.

Frantic, I woke the keeper of our casa particular from his afternoon siesta. I’d left my backpack in a taxi that ferried me minutes before from an artist’s home gallery several miles away back to our Old Havana rooms on the third floor of a private home. The taxi had been summoned by a phone call to the dispatch service, so there was a prayer that we’d be able to track down the driver.

An hour later, my bag was back in my hands.

In Miami, New York or London, the chances of retrieval would have been nil; if the cabbie hadn’t snagged it, the next fare likely would have. But in Cuba, where resources are so much more scarce, my bag arrived promptly with jacket, notebook and guidebook securely inside.

Everything you’ve read and heard about Cuba is true — exponentially. The country is frozen in a time warp where teams of oxen plow the fields, a 1950s Lada counts as a prized luxury and wireless internet access is a fantasy.

But more than the crumbling glory of this Miss Havisham city or the retro thrill of zipping through Havana in a shiny ’50s Fairlane convertible, what seemed most remarkable about our recent visit to Cuba was the constant graciousness of strangers. The friend of a friend who took time off from his post-retirement job to show us around his city. The Coco-cab driver who helped my traveling companion find an out-of-the-way location — and never charged extra. The woman who performed reiki on my knee after I’d tripped on the cobblestones (and wouldn’t take a CUC for her troubles.)

As a first-time visitor, I can’t say whether the warmth was a natural all-for-one sensibility forged by the long struggle of living in a place where a bar of soap costs as much as 10 percent of an official monthly salary, or whether it was part hustle, or whether it came from a sense of anticipation following the recent government rapprochement. “Soon,” so many people said to us. Soon maybe the U.S. embargo would be lifted. Soon maybe there would be more jobs. Soon.

Making it there

With the thaw between the U.S. and Cuba, traveling to the island has become far easier — and legal — for many Americans. Though pure tourism is still prohibited, traveling for cultural, educational and people-to-people purposes is now as simple as booking a flight and filling out a form attesting that your trip qualifies.

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Whether one should go is another subject. For my traveling companions from Oregon, the question had long been only a question of legality. January’s changes in U.S. travel licensing regulations put them squarely in the approved category. To them, the Cuban revolution, the missile crisis, the failed Bay of Pigs invasion are historical relics. But in Miami, the decades often feel like yesterday. The loss of family, friends, businesses, careers, homes is a wound that hasn’t quite healed and for many never can. The question of whether to visit Cuba remains intensely personal, forged by experiences that perhaps no non-Cuban can fully appreciate. Myself included.

Yet even here in Miami, so much has changed. Local performances by Cuban artists once drew passionate protests; today, artists keep studios both here and in Havana. Family members on both sides of the Florida Straits regularly travel back and forth, and even some of Miami’s best-known Cuban-born citizens have returned to visit. As of late May, Cuba is off the U.S.-designated list of terrorist nations.

As a travel writer, for decades I’ve chased the edges of change — China in 1985, Russia during Glasnost, Vietnam as the embargo was lifted there. With history unfolding a mere 45-minute flight away, this spring was the time to go.

Our gang of four had plenty of company. More than 3 million foreign visitors came to Cuba in 2014; another 371,000 came in January 2015 alone. During our March visit, Old Havana’s stone lanes were jammed with Europeans and Canadians wandering through the art galleries and museums, picking the sweet meat of langostinos from their shells. A cruise liner from the French-owned company Club Med sat moored at the pier.

Tourists mobbed the various Hemingway haunts: the rooms in the Ambos Mundos hotel where Papa sometimes lived; the bar at La Bodeguita Del Medio, which claims to have created the mojito; and the Ricky Ricardo-style Floridita, where a bronzed Papa leans forever at the bar, presumably awaiting his beloved grapefruit daiquiri.

Even on a Monday night, snagging a table at the popular paladar, Dona Eutimia, was a matter of luck.

Hotel rooms may be one of Cuba’s scarcest commodities; all are either government-owned or built with foreign minority partners, and the tour we had originally considered joining sold out of rooms. We turned instead to a casa particular booked via an online site at what, in U.S. terms, is a bargain: $30 per night for a clean, simple air-conditioned room with private bath in a third-floor walk-up — a private business allowed as the government coffers have dwindled. Another $5 per person brought us a fresh breakfast of fruits, bread, coffee and eggs cooked to order, served on a breezy terrace overlooking a shamble of clothes-line-draped roofs.

We shared the four-bedroom apartment with our innkeeper’s mother and stepfather; the other two bedrooms go to guests like ourselves. The place looked — and felt — like a beloved abuela’s home, draped with lace doilies and bubbling with family friends, the cook and a housekeeper. Our innkeeper, Cha, graciously let us use his phone (forget using an iPhone in Cuba) and send critical emails on his computer (innkeepers are allowed access), arranged an English-speaking driver to Trinidad, and chased down the taxi with my errant backpack.

The casa was located a bit farther from the center of town than we might have wished, but staying on a street otherwise devoid of tourists offered authentic glimpses of daily life. Students in starched uniforms walking to school. A pair of men pushing a hand cart loaded with strands of onions. Old men lounging on a stoop; a hairdresser fashioning an elaborate coiffure through the open shop door. A horse cart rumbling down the street alongside a 1920s vintage car and a new SUV.

A bicycle taxi waited on nearly every corner, poised for the ongoing game of haggling over the fare. Even in Spanish, giving the name of the destination didn’t always produce the desired results. Not everyone who lives in Havana knows the geography by place name.

The tales of a Paris in the tropics, we discovered, is no myth. The standard hourlong city tour in a classic convertible takes in wide boulevards, domed government halls, rainforest-like parks and a vast marbled cemetery rivaling any in Latin America. Palaces-turned-hotels and colonial plazas are glorious still, often restored thanks to UNESCO efforts. Private mid-century modern homes in artist-centric neighborhoods convey a breezy grace that has largely disappeared from South Florida.

The enormity of what Revolution-era exiles left behind morphed from hologram to reality as we strolled from the government telecommunications store — its door nearly always mobbed by locals waiting to get in — along Calle Obispo past a “pharmacy” whose shelves are lined with old-fashioned ceramic jars and on to the Plaza de Armas, where a troop of musicians and stilt-walkers entertained and traditionally dressed women posed for tips.

Chords from guitars and horns — sometimes with rhythm marked by teeth rattling in a bony horse skull — spilled out of cafes and parks and bars with a fire that had people literally, spontaneously, dancing in the streets. Cubans live in the streets, we were told, and we found it true; nearly every doorway was open and every balcony filled with someone watching the cars, pedi-cabs and horse carts roll by, smiling and waving as we greeted them.

Havana is an art town, and discovering it was part of our mission. A guided walking tour led us through several Old Havana galleries, the 50-year-old Taller Experimental de Grafica cooperative, where master members create the engravings from which they will print; and the Cuban art wing of the national art museum.

More we discovered on our own, stumbling into dens along Calle Empedrado that were as much hangouts as galleries. Many artists keep their gallery hours in their homes, and the end of most days found us chatting about art and life with magic realists, contemporary sculptors and photographers whose emails and phone numbers we had cadged from art-savvy friends before leaving Miami.

Much of the rest of Havana seemed to crumble while we watched. In the central district, rotting facades line main thoroughfares. Industrial complexes on the airport road are gnarled with rust. Even in the corners of the tourist-friendly Old Havana, the garbage bins overflowed for the full week of our visit.

Out of the city

Beyond the capital, the long road to Cuba’s south was lined with loamy fields, some filled with bounty, others left fallow. Cienfuegos was a pastel fantasy, its central plaza guarded by stone lions and rimmed by gracious domes and an opera house. In the souvenir market at the corner, a woman sold us wooden toy cars with help from her niece; the girl was visiting from her family home in the Miami neighborhood of Westchester.

Further down the road, colonial Trinidad shone with touristic prosperity; we were told that the fresh blue house on the corner was for sale for $250,000 — astronomical in a country where private home sales are a recent phenomenon. The town was packed; the owner of our casa explained she was planning to expand to add more rooms for guests.

By day, cowboys, tractors and locals carrying eggs fresh off the finca rolled past shops with handmade sweaters, a massage studio and welcoming restaurants — one with a giant stuffed gator on the steps. At night, the stone streets seemed to vibrate with visitors strolling from their dinners in crystal-laden homes-turned-restaurants through waves of samba and salsa spilling from clubs and plazas; $4 bought a frothy piña colada served in a pineapple from a window along the way.

Even here, the woman who sold us exquisitely hand-tatted tablecloths asked if we had a “gift.” Shampoo, toothpaste and even underwear are in painfully short supply. The shopkeeper to whom we gave our gift package of boxers got teary.

But throughout the country, conditions are better than a few years ago, people told us. Renting out rooms for 25 or 30 CUCs per night creates substantive cash flow in a country where the average monthly salary is the equivalent of 20 to 40 CUCs, with a CUC reckoned around $1. (Well, 87 cents when you take in the government surcharge on changing dollars.) The handmade necklace and ring that felt like a bargain at $15 were a windfall to the woman who had made them.

Our English-speaking driver earned $330 for our overnight trip for four — even after expenses, far more than he once made as a government engineer with several advanced degrees.

Education and health, he pointed out, are two arenas in which Cuba excels. What one can do with that education is still limited. His son, now entering college, might find a better job, he hoped. If relations normalize. Soon.

Throughout the cities we saw, the hammering of renovation rang through the lanes. Shop fronts, homes-turned-restaurants, museums and even private houses are undergoing a collective facelift. In old Havana, the nightly flamenco show at the club La Tableau is just a few steps from a Buena Vista Social Club-style dinner club; in Plaza Vieja, tourists down frothy beer served in five-foot-high towers. Vintage taxis handed down from father to son gleam with polish — though they’re still held together with wire and bubble gum.

Our final evening was a celebration of sorts. Drinks at the historic Hotel Nacional, less shiny than in the decades when mobsters and Hollywood stars filled its bars, but still with the same seductive view across the Malecón and the sea beyond. Dinner at a rooftop paladar, where the ginger fish rivaled what you would find in Miami in both presentation and taste (though at half the price.) Jazz at la Zorra y El Cuervo, where the $20 entry fee included two cocktails more watery than the worst of college days. The audience, mostly foreign, included a South African government official.

Drivers clamored at the club exit; we grabbed the first and headed across the street to his car. The engine burped and gurgled; the floor was pocked with open spots, and we prayed the rusting Lada would survive the two miles back to our rooms. Prosperity hasn’t trickled down quite so far yet.

At the desk of our historic hotel was a message from our friend of a friend. Along with taking time away from his job, he and his wife had escorted us to the San Carlos fort, where an 18th-century cannon-firing is re-enacted each night. With a monthly retirement stipend of $13, taking us out to a dinner was impossible, and we had too little time to come to their home. Instead, as a parting token, he had left us beautiful earrings and carvings, and promises to call us when he comes next to Miami, to visit the son who lives here.

Whether the U.S. embargo will be lifted — and whether it should be — is a matter for others to decide. One way or another, change is coming to Cuba. Soon? It’s already under way.

Follow the travels of Jane Wooldridge at, on Facebook at the Five Stars to Under-the-Stars page, and via Instagram @janewooldridge.

If you go

Who can go: Americans can now visit Cuba for a range of religious, cultural and educational purposes. (Those with family in Cuba or who were born there have been able to visit for some years under separate regulations.) Before your airline booker arranges transport, you will be required to fill out and sign a form verifying the purpose of travel.

Getting there: Currently, all air transport is through charter flights that can be booked through one of Miami’s many local charter companies (we used Airline Brokers) or via

Traveling mindfully: We focused our shopping, lodging and dining on privately owned establishments where money goes directly into the pockets of locals. Private restaurants are called paladars; private lodgings are casas particulares. Where just a few years ago both were informal, homespun affairs, they are rapidly increasing in sophistication — and price. Locals appreciate simple gifts of toothpaste, shampoo, soap and underwear.

Where to stay: Old Havana is the top draw for most tourists, and the most convenient lodgings are in former palaces located in the areas around Plaza Vieja and Plaza de Armas; all can be booked online at, the government site that takes U.S. credit cards. The famed Hotel Nacionel, modeled after The Breakers in Palm Beach, is located on the Malécon in the Vedado area; it too is surrounded by restaurants and tourism facilities. Hotel rooms are in extremely limited supply; we actually built our trip around scoring a few precious nights at the Santa Isabel. Hotel rooms are generally priced $150-$300 per night. We arranged our casa particular through the website and paid on arrival; it cost $30 per night. Since our visit, Airbnb ( has begun operating on the island, and prices have started to rise.

Dining: Paladars generally have more innovative cuisine and more attentive service than government restaurants. One exception is El Templete, behind the Plaza de Armas, where service, presentation and the lobster proved as remarkable as anything in Miami. In Vedado, the rooftop paladar Cafe Laurent surprised with smart cocktails, chic ambiance and an outstanding ginger fish; Atelier, also in Vedado, wins raves for its old-school ambiance and French-inspired dishes. In Old Havana, the snug paladar Doña Eutimia stands out for Cuban standards with a culinary twist, such as lamb ropa vieja. Most meals are priced around $15-$20 per person, plus drinks. Cocktails are a bargain by U.S. standards; only at the priciest tourist traps will you pay more than $4 for a daiquiri or mojito.

Money: American credit and debit cards don’t work. You will need to take cash. The government charges an additional fee for U.S. dollars, which translates into a rate of 87 cents per 1 CUC, the convertible currency used by foreigners. Canadian dollars and Euros trade at a more favorable rate but changing U.S. dollars first to one of those currency can cost as much as simply using U.S. dollars.

Getting around: Auto taxis, bicycle taxis and the bright yellow motorized pods called Coco taxis are plentiful. All rates are negotiable. You’ll get overcharged the first time or two before you figure out the going rate. Don’t fret; it’s only a couple of bucks.

Language: While many people do speak English, many don’t. At least rudimentary Spanish is extremely useful.

Communications: No, your iPhone will not work. Internet cafes don’t exist. Many hotels do offer wireless for a fee, but service can be spotty.

Tours: Some private tours are offered in Cuba; your hotel or casa owner can always make arrangements. If you’re planning to take a private car around the island, a car with driver is highly recommended; be sure the car is in good condition. Various tours can be booked in advance from the U.S. Among the better-priced options are those offered by Authentic Cuba Tours,

Cruises: Several highly regarded small-group cruise companies are offering sailings around the island this winter. Group IST ( will begin sailing its second season of trips. New will be sailings from Vantage Travel (, International Expeditions ( and Zegrahm Expeditions (

Information: Moon Guides and Lonely Planet both publish useful guidebooks that can help smooth the way.

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