Hi vpas, i will comment in general but if you need a specific info about something just ask.
Cuba has lots of winds, normally 10 months out of 12 are really good, from 15 to 24 are the most commons ones, there are exceptions as well. July and August, if you can, avoid them; is beautiful in that time but the winds can be very low for 2 to 3 weeks in a row, unless there is a tropical storm or hurricane getting born near by and that will make the low wind months boost up.
So far from my experience, the best winds and spots are in Varadero, you can find places to ride with all kind of winds directions, from Varadero you can visit Habana if you are looking for a bit more than just kiting, is only 1:45 hours more less, the city of Matanzas at 35 min has amazing landscapes and places to visit. (the downwind is insane in Varadero) 30 km long and more if you keep going to “Boca” (town located 10 km outside)
Varadero has so much things to do that you wont have time for all of it. About hotels, most of them are all inclusive, from 2 stars to 5 plus, it depends on your budget to choose which one is the right one, in all of them you can kite with W, WN, N, NE winds, if you find the E, S or SW (offshore) you simply go to the other side of the peninsula, is not as nice like the beach but it will work. there also a handful of hotels that you can stay and pay with cash, or VISA, from 25 to 55 or 65$ depending on the rooms breakfast include or not etc.
note: NE wind is the dominant ones in Cuba.
I still havent post the map with the spots but I will do it as soon as i have a break , I have missed to tell a bunch more of information, as I say before, let me know what else you need and I will keep posting it.
charley aka charlito