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When somebody mentions Cuba, there are several associations that people usually think of, things like Cuban cigars, rum, their well known rhythms or revolution and Che Guevara; communism. There is absolutely nothing wrong with connecting all that to the idea of Cuba, but the truth is that Cuba offers much much more. Probably combination of it all, but either way more than good for anyone traveling to Cuba.
The thing that any future Cuban explorer should have are basics in Spanish, if not then good Spanish dictionary is a part of compulsory baggage, their English is really not good. Since most of the time tourists book rooms in one of the numerous Casas Prticulares , which are rooms with bathrooms in their family houses with breakfast or other meals as well, the ability of at least understanding Spanish is really useful.
Prices: 20 to 30 dollars per room per night. All Casas Particulares around Cuba have the same sign light blue reminding of anchor and prices are also almost the same no matter where you go, but the quality can vary a lot. The owners of the houses know each other all around the Cuba, sometimes leaving you with the feeling they are some kind of secret organization.
When it comes to Cuba there is also one really specific thing about staying there, popular couchsurfing is forbidden. One of their laws simply forbids Cubans to have foreigners spending night at their houses, unless they have a room registered as a part of Casas Particulares system, since in this way country gets its commission and can easily control everything.
Unfortunately that kind of image is far from truth. The truth is that almost every restaurant, coffee place or a bar has some Cuban musicians playing every night, you can also find them on many squares, but as you could have already realized, these are all places where tourists go.