Hi. I do not think that 1000 USD is enough. You might be able to use only 1000USD, but it will be a tight budget. There will not be much space for anything extra. It also depends a lot on what kind of a spender you are. If you are very frugal, then it will be ok. But if you like to drink and have fun, you will need more money. It also depends on how many friends you are going with and how much money they bring. If you are going with 2 or 3 other friends and you will be sharing the cost of taxis and rooms with them, then it will be ok. But if you will be taking a taxi by yourself and renting a private apartment, then your money will go very fast.
The usual recommendation for money is to bring about $100USD per day.
Also, there is still the 10% penalty on USD exchange. So your 1000USD will only be worth 900$ USD once you get to Cuba. The penalty is supposed to be removed soon, but as far as I know, it is still in place.
As for places to visit. I would say Habana, Varadero and Giron are good places. Also, you might like to visit Trinidad, which is about 2 hours east of Giron. It is a very popular place with nice architecture and nature. Also, near Trinidad is the Topes de Collantes natural park which is very beautiful.
I hope this helps.
Mario
