Just got back from Cuba - we did a little over 2 weeks there, travelled on our own. This was the
general itinerary:
1/ Havana (2 days) - more than enough it you ask me, there's not that much to see
2/ Island of Youth (4 days) - this was quite tricky trip - i'll post detailed info on this one.
3/ Havana -> Santiago de Cuba (1 day) - on the bus (Viazul, 14 hrs, ~52 CUC), then rent a car
4/ Santiago De Cuba (1 day) - even worse than Havana, 1 day max
5/ Cayo Coco (2 days) - western-standard hotel resorts, not very cuban :)
6/ Trinidad (1 day) - nicest city in Cuba imho, 1 day is enough tho (it's very little)
7/ Varadero (2 days) - hotels & resorts...
8/ Playa Larga (2 days) - excellent for scuba diving, lots of moskitos!
9/ Havana (1 day) - flying out
Money - as foreigner, you have to use CUC (~1.1 USD, closer to EURo now tho) which you can change in banks (or if you get lucky and spot ATM). The prices are quite high, at least for foreigners - locals get things much cheaper.
Hotels / Casas Particular (CP) - we combined both, never had problem finding CP - usually ppl approach you on the street (especially when you get off the bus) and try to hook you up. They can be a bit annoying, but not too bad. All the CPs we used were very nice and clean, separate bathrooms, etc... Definitely worth the 15~25 CUC you spend. They like to offer food (b,l,d) - couple of times we tried it and it was always very good as well. Hotels were ok - Cayo Coco & Varadero were very nice (~100 CUC tho), Playa Larga was a bit run down (~60 CUC) with a lot of insect sharing our room :)