At the risk of coming off as crass and vulgar, Cuba is a shithole.
The food's terrible, smog in Havana is the worst I've seen anywhere (most cars don't have mufflers and are poorly tuned), the locals try to screw you over any chance they get (Beijing Tea Room type scams are commonplace, especially in bars - just don't talk to anyone who acts friendly and tries to bring you into a shop, and NEVER EVER accept local currency or any gifts), and the whole place is so dilapidated (except for the small touristy section of town) that it's amazing the buildings are still standing (most balconies in concrete buildings have long since collapsed). I watched in Trinidad as local workers dug up part of a cobblestone road, then filled it back with plain dirt. Most of the roads people have worked on are completely washed away from the rain (the ones they haven't touched are still fine).
You can have good food and a pleasant stay if you go to a resort, but then what's the point? You could be at any resort in the world and have the same cookie-cutter experience.
Oh, and if you do go, bring a currency OTHER than USD because the Cuban government controls all currency conversion, and trades USD at a severe disadvantage compared to other currencies.
The food's terrible, smog in Havana is the worst I've seen anywhere (most cars don't have mufflers and are poorly tuned), the locals try to screw you over any chance they get (Beijing Tea Room type scams are commonplace, especially in bars - just don't talk to anyone who acts friendly and tries to bring you into a shop, and NEVER EVER accept local currency or any gifts), and the whole place is so dilapidated (except for the small touristy section of town) that it's amazing the buildings are still standing (most balconies in concrete buildings have long since collapsed). I watched in Trinidad as local workers dug up part of a cobblestone road, then filled it back with plain dirt. Most of the roads people have worked on are completely washed away from the rain (the ones they haven't touched are still fine).
You can have good food and a pleasant stay if you go to a resort, but then what's the point? You could be at any resort in the world and have the same cookie-cutter experience.
Oh, and if you do go, bring a currency OTHER than USD because the Cuban government controls all currency conversion, and trades USD at a severe disadvantage compared to other currencies.