Cuba

Is great!
First of all, Cubans are unbelievable friendly people. It is somewhat sad that this should be the biggest culture shock when visiting a country, but it was. I realized how absurd it was, when I spoke to several other 'western' tourists who realized they had to get used to people trying to be genuinely friendly to them.
For some reason we seem to expect that when strangers are being friendly, they are trying to get money from you or are trying to distract you so that their partners can rob you.
Off-course there where a lot of people trying to make some money in Cuba as well, but it was in a decent way.
For example: we were checking out an old building in Havana. A couple stopped to tell us about the history of the building and why it was in such a bad state now. After the explanation they asked us to buy some milk for their baby. They wouldn't accept any money, they really wanted us to come to the shop and buy them milk. Sure, this is also a form of hassling (especially with the prices of baby milk nowadays, but it's the most sympathetic form of hassling I personally ever experienced.

Now if anybody feels the need to inform me that Cubans are known to mix crystal meth with baby milk for consumption, please do so I can restore my pessimistic world view.