The largest island in the Caribbean and an independent country – and a pretty unique one: ruled by one of the longest-standing communist regimes in the world, originally under Fidel Castro, from the revolution in 1958/59 to 2008, when power was handed over to his brother (and Fidel passed away in November 2016).
The country has been an arch-enemy of the USA all through those decades, and in 1963, the Cuba crisis, when the US blockaded the shipment of Soviet nuclear missiles to be deployed in Cuba, brought the world closer to World War Three than ever before (or since).
After the collapse of the USSR (always Cuba's most important ally) and the end of the Cold War, Castro had to look for new allies, but continued his rule unabated. Today, alliances lie rather closer to home, e.g. with nearby Venezuela, though China also continues to be important.
The role of a defiant state insisting on being a thorn in the side of the USA, so close to the latter's territory, has always made Cuba rather special and earned it sympathies from other less US-friendly sides all over the world. And it also makes for a certain quirky, if not outright dark attraction to foreign tourists. I've lost count of how often I've heard people say they want to go and see Cuba before it changes its character, which everyone presumes it will in the post-Castro years to come.
To get a feel for it, however, one must stay away from those tourist "ghettos" that have sprung up on the coast. They also don't give much back to the country – they're basically beach resorts and as such offer nothing to the dark tourist.
The poverty in the country is pretty bad and visible, though, due to the economic hardships brought with the system.
However, if you, as a dark tourist, expect any signs of eccentric cult-of-personality about Castro, you may be disappointed. He may have been feared for his whims and endless speeches, but he never actually engaged in much Kim-Il-Sung- or Ceausescu-like cult-of-personality extravagances. Nor will you be able to see anything of the concretely darker sides of the oppressive system (apart from the absence of a free press).
Another Cuba-associated type of cult of personality, albeit largely posthumously, revolves around the legendary revolutionist Che Guevara. He was murdered ("executed") in 1967 in his native Bolivia by CIA-led "special forces", but in 1997/1998 his rediscovered, exhumed body was transferred to Cuba  for re-burial in a grand mausoleum in Santa Clara. So that may also be a destination for Che-inclined dark tourists.
Another particularly dark site on Cuba is not actually Cuba's either but even belongs to the USA: Guantanamo. The US have maintained a Navy base here since 1902 and have held on to it to the present day. The name has assumed particular notoriety since 9/11, namely as a special extra-territorial prison camp which the US set up here and to which they deported numerous terror suspects captured in Afghanistan and elsewhere. The legal framework of all this is more than dubious. In addition, it is widely suspected that interrogation methods at Guantanamo constitute torture. All this has brought the US government under George W. Bush harsh and widespread criticism. His successor Barack Obama pledged to close down Guantanamo years ago, but the fulfilment of that pledge never materialized ... So the camp still remains in use today.
For the dark tourist, the Guantanamo site can obviously not be visited in any case – and whether that may ever change when it's closed down is also questionable. As the naval base will most likely remain a restricted military area with no access for civilians. For the time being the only option is to look down on Guantanamo from a hill on the Cuban side of the "border" … (see, the relevant section in Tony Wheeler's "Bad Lands")    
Apart from the above and various other sites related to Castro and the revolution (e.g. the Moncana barracks in Santiago, Morro-Cabaña in Havana, or the Tren Blindado in Santa Clara) there's also a unique cluster of large circular prison buildings called Presidio Modelo (model prison) dating from the time of the pre-revolution Batista dictatorship. Both Fidel Castro and his brother were once imprisoned here. The complex was closed in 19667 and subsequently turned into a memorial. This outstanding relic is located not on the 'mainland' island but on Isla de la Juventud, south of the north-western tip of Cuba, requiring a domestic flight or ferry crossing to get there. 

©, Peter Hohenhaus 2010-2019

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