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Barrelling through the vibrant streets of Havana in a neon-yellow 1950 Cadillac DeVille, I turn to my guide and gesture around emphatically – at the baroque-style edifices, the meticulously restored homes, and the locals leaning over ornate, second-floor balconies, observing the scene below.
“Your country is so beautiful,” I say, in that oft-used and cliché observation of being a stranger in an attractive foreign land. A strange look crosses her face.
“Yeah, it is. For you,” she replies, smiling. “For us, not so much.”
As we quickly discover, complimenting anything in Cuba can be a complicated affair.
As a Kiwi expat living in Canada, Cuba is frequently touted as a cheap and easy holiday destination. Come winter, sun-deprived Canucks flock to the white-sand beaches of Varadero, staying in government-run resorts on all-inclusive packages.
For the rest of the world, a trip to this Caribbean outpost of communism is decidedly more difficult – thanks to President Donald Trump placing it back on the nation’s State Sponsors of Terrorism list, in one of his last acts in office.
Cuba is also in the grips of one of its worst economic, political and energy crises in a century, prompting a mass exodus from the island.
Last year, the numbers of Cubans seeking entry to the US leapt from 39,000 the year before to more than 224,000 – amounting to 2% of the island’s entire population.
Acute shortages of food and medicine, and power outages are a daily reality. An ill-timed currency reform, which merged Cuba’s two currencies in 2021, pushed inflation to unprecedented levels.
Gone is the optimism that abounded in 2016 – when President Barack Obama re-engaged with the island six decades after the US imposed its crippling trade embargo.
A thriving black market means the phrase “change the money?” will be levelled at you everywhere you go, from savvy, but desperate, locals offering to buy US dollars at rates much higher than the local banks.
But if you’re the sort of traveller looking for a holiday with a side of challenge, this is the time to visit. There are no crowds, few tour buses, and the locals need those tourism dollars now more than ever.
“It’s a mess, it’s a real mess,” Bell, our guide from Old Cars Havana, laments. She initially wanted to be a teacher, but being a tour guide pays more.
Tourism is one of the most lucrative sectors in the country for Cubans, because travellers can pay them directly. State jobs, on the other hand, pay an average of US$25 (NZ$40) per month.
That’s also why owning a classic car can be a financial boon. These are the island’s “trophies,” Bell says, but also a necessity. Due to the trade embargo, importing cars is hugely difficult – and hugely expensive.
Bell shows us a chart on her phone that shows a 2012 Toyota Corolla on sale for US$55,000. When the US cut the country off in 1962, Cuba was left with the cars on the roads at the time (and a fair few Ladas, leftover from the Soviet Union’s role as principal backer) and has had to make do since then.
But, contrary to popular belief, you can’t just hire one of these for the day yourself. Driving classic cars for tourists requires a special licence, Bell explains, which takes two years to obtain. Tourists hire a driver (usually the owner) and the car for about US$130 for a three-hour excursion.
Habana Vieja, the city’s venerated old town and a Unesco World Heritage Site, however, is best explored on foot.
The result of a groundbreaking historical renovation project, along the narrow lanes you’ll find Spanish-built fortresses, towering cathedrals, and vibrant plazas hemmed in by edifices of Cuban Baroque and Art Noveau.
The fresh lick of paint among the buildings here stands in a stark contrast to those in just a few blocks in either direction, where homes are literally crumbling around people. And, unlike those of Dubrovnik or Venice, locals still live here – about 100,000 of them.
Just a few blocks over from tourist-heavy El Floridita (Ernest Hemingway’s bar of choice for a daiquiri) or El Bodeguita del Medio (where he went for a mojito), locals are queueing outside markets for their monthly food rations.
Bell shakes her head again as she walks by a crowded market, explaining that she’s taken to forgo her rations for the month in favour of a day’s work with tourists. It pays more than the rations are worth.
“We love our country, we love our culture, but we hate what the government is doing to it,” she says.
She’s not alone. Almost every local we spoke to in Cuba was forming an escape plan.
“This is a prison,” one taxi driver, who was saving up to move to Barcelona, told us. His wife is a psychologist and earns in a month (US$30) what we’d just paid him for a single journey.
Food shortages mean Cuba is not the destination for gourmet fare. Butter is almost impossible to come by anywhere, there are shortages of milk, and delicacies such as fresh fish are often exported or sold at an extortionate price.
Accommodation, however, is a surprising highlight of Cuba’s underdeveloped tourism industry. Especially if you choose to stay at a casa particular (which literally means ‘private home’), where Cuban families register their homes as privately-owned businesses and rent out rooms to foreigners.
One of the best is Casa 1932, run by the enigmatic Luis Ulacia in the gritty suburb of Centro Habana – home to palatial buildings (renovated and in various states of ruin), celebrated jazz clubs, leafy rooftop bars and much-lauded restaurants.
Ulacia, a former pharmacist, offers two rooms in the home his grandfather built in 1932, and in which his mother, daughter and son-in-law still live. Furnished with his grandfather’s original furniture and much of the original decor, it’s an all-consuming step back in time.
But for Ulacia, it’s about much more than lodging a couple of backpackers. He takes hospitality seriously – taking note of nationalities of incoming guests and tailoring their rooms to their needs. British people get a kettle with tea, for example.
“I love it. This is my life,” the jovial Ulacia says, ferreting around in a cupboard in the breakfast room to put a George Michael record on. He’s also a rare Cuban who doesn’t want to leave the country and refuses to speak about politics.
So, naturally, Ulacia doesn’t admonish the luxury, government-run hotels that dominate central Havana. He thinks tourists should try both ends of the spectrum.
“You should travel and you should see it all, and then you should decide what you like. This is part of Cuba. You can’t hate it, because you would break Cuba.”
And, indeed, staying in one of Havana’s luxury hotels is a world away from the city’s current reality.
Located on the edge of Habana Vieja, the 246-room Gran Hotel Manzana Kempinski is housed in an imposing early 20th century building (once Cuba’s first shopping arcade), and occupies an entire city block.
West-facing balconies overlook Parque Central, a gathering spot for classic car owners in the morning as they polish their paintwork, and the gargantuan white dome of the National Capitol Building – a White House-esque landmark that Habaneros will only too happily tell you is bigger and richer in detail than its doppelgänger in Washington DC. The rooftop bar and pool is well-known by locals and tourists alike as the place to catch a sunset over the city.
Two blocks away, the Kempinski has just opened a sister hotel: Gran Hotel Bristol La Habana. It too has a rooftop pool and terrace, and panoramic views of the city.
The rooms in both are opulent – stocked with five-star amenities, plush beds and attentive staff – but even they can’t escape some of the trappings of modern-day Havana. A faulty iron might still burn a hole in your shirt. Your first menu choice at the restaurant might not be available.
However, the breakfast buffet is where the differences really become clear. There’s a ready supply of milk and a giant bowl of butter. And right now, that’s the true measure of luxury.
New Zealanders travelling to Cuba can fly via the US, Mexico or Canada. However, if you’ve flying via the US, you will need to apply for a Cuban tourist visa, which stipulates that you must spend your money on businesses and accommodations owned by locals.
Travelling to Cuba will also make you ineligible for the ESTA visa waiver programme in the US, meaning you’ll have to apply for a B-2 tourist visa if you’re planning to transit through the US or visit after you’ve been to Cuba.
Carbon footprint: Flying generates carbon emissions. To reduce your impact, consider other ways of travelling, amalgamate your trips, and when you need to fly, consider offsetting emissions.