I went back from Havana to Europe 3 days ago. For two weeks I've been traveling around the western part of the island - Havana, Vinales , Trinidad , Varadero. I went solo, with only very basic spanish. And I have to tell you that it was great :D.
I was meeting new people every single day, Vinales and Trinidad were full of tourists from Europe, Havana was more difficult but it also had some people to socialize with outside of jineteros.
It was expensive, I was spending on average cuc per day, but I was partying quite a lot, and I lost about 30 - 50cuc on jineteros during the first days in Cuba. The Nate hurricane passed next to Cuba while I was there, so 3 days were really rainy and cloudy, thus I was staying in Havana for about 6 - 7 days.
The food was all right in general. Price differences were huge everywhere - you could take yellow taxis or taxi collectivos. Taxi to the airport was 25 - 30cuc, but taxi collectivo to playa santa maria was 2cuc around the same distance?
I learned a lot of spanish while being there. If you're looking for a casa in Havana, I can recommend you Casa de Mary near malecon m from la rampa marina street. It is 25cuc per night, you can bring cuban girls inside : And they are very nice and helpful. Next casas can be very, very easily arranged in Cuba, by just asking current casa's owners.
