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Cuba – Expat Heaven Or Hell?

The death of Fidel Castro sent political shockwaves through the Americas as the the figurehead of Cuba’s revolution slipped into the history books. The socialist state he fought to found has already changed much in recent years, with the country’s Marxist philosophy softening. The death of the revolution’s leader is just one further step toward the opening up of this secretive island state.Castro’s troops may have marched to power in Havana without any American objections, but when the Cuban leader announced his Marxist policies, the United States reacted quickly.

The White House slapped a trade embargo on the Island, preventing American businesses from dealing with Cuba. Although the tiny island posed little military threat, a communist nation just 90 miles from the Eastern Seaboard was a serious political embarrassment for the superpower.

The US rigidly enforced sanctions against Cuba and pressured other nations into severing ties, leaving Castro’s revolution with the Soviet Union as its sole trading partner. Even this stalwart supporter abandoned Cuba when turmoil hit Moscow in the early 90s.

As the Cuban economy reeled and the currency hit rock bottom Castro announced the beginning of ‘the special time’, a period of food rationing and austerity that saw barren supermarket shelves and decaying infrastructure.

Cuba, Castro and his revolution survived these troubled times and rebuilt the island state into a fully functioning, if quirky, economy. The island functions on two currencies, all beef is owned by the state and government agents can force drivers to pick up hitchhikers. The Cuban government still controls all media and evidence of communist policies are everywhere.

Even with red stars adorning Havana’s government buildings, Washington has noted changes in society. The average Cuban can now own a house and a car, enjoy access to the internet and change Cuban Pesos for American Dollars – freedoms denied until recently.

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Cubans still remember the time before Castro’s revolution, when Cuba had high infant mortality rates, low life expectancy and the worst literacy rate in Latin America. Islanders now enjoy some of the world’s best healthcare for free, free education at all levels and a life expectancy on par with the USA itself. As much as they appreciate what the Revolution has done for them, Cubans are also hungry for economic progress.

As the revolution’s hard line softens, the people are seizing opportunity with both hands, setting up businesses and making money. The United States responded to this in 2015 by historically softening the trade embargo to allow travel to the island and businesses to trade with Cuba individuals and businesses.

Cuba, once home to the king of hell-raising expats Ernest Hemingway, is rapidly becoming a choice destination for those looking to grab a slice of Caribbean sunshine as well as those hoping to strike it rich as the economy blossoms.

What opportunities does Cuba offer? Is this island paradise really ready to welcome an influx of foreign residents? Are you ready for life in a Marxist state? Could Cuba be the next hot ticket for expats? We’ve taken a look at what every potential expat needs to know before moving to Cuba.

Watch the weather

While the world is focused on Cuba’s economic forecast, it’s important to remember that the island is frequently hammered by hurricanes and tropical storms.

Whilst the island paradise may be the perfect place to sip on a Daiquiri for much of the year, there are months when the palm trees bend over backwards and rain floods the streets.

With its rickety infrastructure, Cuba is still struggling to repair damage caused by Hurricane Sandy in 2012. Anyone looking to set up home or start a new business in Cuba should be aware that they may find themselves dealing with power cuts, flooding and landslides during storm season.

On America’s doorstep

It’s still to early to predict a return of Cuba’s heyday of casinos and nightclubs. From the 1920s to the revolution, flights shuttled wealthy Americans to the island to enjoy weekends of hedonistic hell raising.

Should these short flights be reinstated, it would be easy and affordable for Americans to pop over to Cuba for short breaks, or vice versa.

With the lower cost of living and possible tax breaks for Cuban-based businesses, it’s plausible that business may boom in Havana. Close to America but firmly part of the Latin world, businesses in Cuba could find themselves enjoying similar advantages to those in Puerto Rico or the Cayman Islands.

It seems like a big step to go from Castro’s Communist community to a capitalist Cuba funnelling international cash around the world, but it is not impossible in the medium term.


Cuba has had a lot of bad press over the years for the rigidity of its laws and the lengthy sentences that can be handed down for seemingly mundane offences.

Just talking about breaking a law could earn Cubans a six-month prison term, whilst owning pornography can also land you in trouble. Make sure you understand Cuba’s unique laws and the items that may be confiscated from you on arrival. Bags are routinely searched on arrival without their owners present, travellers have reported arriving at their hotel to find that GPS devices, medication and sex toys have all been removed from their luggage without explanation.

That said, Cuba has an incredibly low crime rate and residents are unlikely to be victims of any crime. Of course, tourist wallets are a tempting target for opportunistic pickpockets and the naïve may find themselves victims of the odd con-artist.

The most common form of crime an expat is likely to encounter is low level corruption, where a small gratuity may be expected to speed along official paperwork.

The influx of tourists

Cuba has thus far done a good job of protecting its cultural heritage whilst making what money it can from tourism.

The centre of Havana will be filled with sunburnt tourists paying for rides in rusting American classic cars, whilst the Varadero peninsula is festooned with sun loungers and beach towels. Bayamo is a must-go destination for art lovers whilst Cienfuegos calls music lovers to its bars and clubs. These destinations are readily connected by a line of air-conditioned coaches and state-owned hotels.

Cuba has prevented the local population from giving up their day jobs to chase the tourist dollar, preventing towns from losing the character that first attracted visitors. But as the island opens its doors wider, it seems likely that outside investment will start buying up bars, hotels and shops, employing locals to wait on the tourists.

The novelty value of Cuba as a new destination is likely to drive a big uplift in visitor numbers, but if the island goes all in on this economic strategy, it may be left with a dud hand when the tourists switch to another destination.

There are concerns amongst Cubans that an influx of foreign cash would not be fairly distributed amongst the population, creating a poverty gap that hasn’t existed on the island for over half a century.

Free Healthcare

Cuba’s healthcare system is one of the best in the world, offering innovative treatments to all for free. When world leaders in Latin America get ill, they head to Havana for treatment.

In fact, the Island has long had a thriving business for health tourism, with patients travelling from around the world for procedures as diverse as gender reassignment, organ transplants and cancer treatment.

Of course, there’s always a catch in Cuba; expats used to having a say in their treatment may be surprised by Cuba’s ‘take it or leave it’ approach to care. The doctor knows best and if you don’t like his diagnosis you can go without treatment.

For most expats this shouldn’t be too much of a problem, as a short flight to Florida can get you to a US doctor quickly and give access to a range of treatments that can be tailored to your needs. Just be prepared for to pay the full rate of fees or a premium rate of health insurance if this is your plan.

Cuban Schools

The state school system is widely respected across Latin America. In 1959, under dictator Batista, the literacy rate of Cubans was as low as 60%. The education system at that point was underdeveloped and has suffered as a result of ‘brain drain’ as educated Cubans left the island rather than teaching the next generation.

Once Castro’s bearded revolutionaries reached the capital, they immediately set about a programme of reforms to improve the lives of the average working Cuban. Chief among these schemes was an initiative that raised the literacy rate of all Cubans to over 96% in just two years.

Even after decades of strife and economic hardship, the powers that be still place education as a flagship of the revolution, keeping literacy at a reported 99.7%, a figure which beats both the US and UK.

The government promises free education all levels, from kindergarten to post-graduate. With so many doors open to bright young Cubans, it’s hardly surprising that they reach high levels of achievement, but thus far they have lacked chances to take these skills overseas.

Cuba can proudly boast the most doctors per 100,000 people, with 591 physicians qualified in the populous. The trouble is that there are more doctors than there are healthcare jobs, meaning many highly qualified professionals hang up their white coats in favour of driving a cab.

Expats with kids need to be aware that although the curriculum is taught in tired, crumbling buildings, schools in Cuba achieve high scores and produce ambitious young academics. Sadly, the school system has also been accused of producing brainwashed fervent socialists thanks to the politicised and highly nationalistic content of many lessons.

The option for expat kids to study in international schools is limited in Cuba. There are only two alternatives to the state school system: the International School of Havana and École Française de La Havana. Both are in the Capital.

The future is uncertain

The lowering of the embargo and the opening of doors to international trade can only be good news for Cuba’s economy. But this doesn’t set every Cuban at ease.

The older generations can still remember the time before Castro, when 60 infants of all 1,000 live births would die and life expectancy was below 60 years. Healthcare was expensive and non-existent in rural areas.

The younger generation takes the improvements brought by the revolution for granted, where only five babies in every thousand die and Cubans can expect to live into their 80s. Instead the young look to the consumerist culture and hunger after designer labels and luxury cars.

A struggle for Cuba’s soul is likely to ensue, where the government and people struggle to adjust their society to the sudden influx of outside influences. As new money rushes into Cuba, how much of it will go into private pockets and how much of it will go into government coffers?

Big corporations hungrily eye Cuba as an untapped market, where potential customers wait to hungrily snap up the kind of goods they have been unable to buy for decades. But with an average wage of only USD$20 a month, can the population really afford to splash the cash on toys and trinkets?

As of 2012, 10% of Cubans were self-employed, opening the island up to a world of entrepreneurial possibilities. Cars, homes, workshops and market stalls have all provided a basis for future of small businesses on the island. But will an influx of outside investment spur this fiscal revolution on or quash creativity before it starts?

Without Fidel Castro, the father of modern Cuba, as a steady hand on the tiller the tides of change could carry Cuba into a stormy future. Any expat heading to Cuba should be aware that the next few years will be sink or swim for the island nation.

Article by Andy Scofield, Expat Focus International Features Writer

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