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There are many things that make Cuba unique, or at least pretty different. Here’s a few to start with.
1. Unlike most of the Caribbean, where the population is ethnically, well, Afro-Caribbean, Cuba much more of a melting pot, due to the many centuries of Spanish influence. Thus the population divides into white, black and everything in between (often referred to, and not disparagingly, as mulatto). For good or ill, many of the staff in the top hotels will be white, especially reception staff.
2. Cuba is, as everyone knows, one of the last bastions of Communism. Its near-neighbour, the USA isn’t too keen on this and they’ve not been friends since Castro came to power in 1959. So instead of ads for Pepsi, Coke and Macdonalds plastered everywhere, what you get instead is Communist propaganda, pictures of Che Guevara, and slogans about the Revolution. There is evidence of the ’Russian’ period everywhere (when the USSR was pouring in aid), especially in the trucks you see everywhere. There are more subtle influences too.
3. The government does not, by and large, allow its citizens to travel. This makes them fairly curious about the ’West’ and you get the sense that they are hungry for information, many of them tuning (illegally) into TV beamed from Florida.
4. Cubans have a love hate relationship with their governance. In some ways they see it as intrusive and creating many rules (some that do not even really exist). On the other hand they see it as comforting in that it provides safety. An example was a security guard when in a conversation, could not understand why the Canadian Government would not force Wendy's Restaurant to hire security or provide security for the late night closing staff. This simple example explains a deep issue, in that Cubans have come to expect the government to deal with many things, and further than the separation of the state and business is very vague in Cuba. They see many television shows and commercials about Western culture, (Americanized) and desire things like the Nike Logo caps, but do not understand that a simple hat that should cost pennies, with the addition of that logo is worth many many dollars. It is an almost naive response to what they see but cannot quite understand.