Just got back (albeit from a resort type holiday).
It's a fascinating place, but expect to feel hounded literally everywhere you go if you look in any way touristy. I don't just mean a few people, I mean, the moment you step out of a vehicle expect to have more than one hat on your head, your shoes being grabbed at, your sunglasses being requested and grabbed at etc.
It's a country filled with educated people who have no means to better their life as they are not allowed to build new buildings, nobody maintains the current buildings as nobody feels it is their responsibility and they can have as much coin in their pocket as you like but they have very little they can actually buy with it!
I never felt unsafe in any of the places I visited (though Havana took a lot of getting used to) and found it was easy to feel like you were being treated like a king for very little money.
Saying that, some places in Havana bordered on extortionate, so you have to be careful. For eating out I think I would prefer to find a good restaurant in someone's house (casa) as this seemed to be the only way to get good authentic Cuban food (rice, stewed black beans and stewed meat).
Make sure to have a daiquiri in the Floridita bar in Havana (sometimes called the Earnest Hemingway bar)
http://en.wikipedia.org/wiki/Floridita, well worth the money to say you've done it, good daiquiri too.
Finally, if cigars are your thing, be careful what you buy, consensus seemed to be that nearly all sold outside of a licensed shop will be fake and contain little if no tobacco.
