I have just got back from Cuba. It is a real trip. I have been there 3 times and I consider this island as one of the windiest place in the Caribbean. The only problem is transportation and to be at the right place at the right time.In the winter as a cold front is coming the wind tends to start blowing from the south and in that case you should head to the central south coast something between playa larga and trinidad or to Varadero to the very end of the peninsula, then it turns northwest to northeast and at that point it can be quite strong and rough the right spots could be anywhere on the north coast between playas del Este, 20 miles from Havana to the cayos. The whole weather pattern may last a week until a new cold front comes. If you can't move around then consider staying in Varadero there are cheaper private places at the beginning of the peninsula, ask around. If you want to travel around, which seems to be the more interesting option, you'd better speak good Spanish and be ready for the unexpected. Last but not least you will probably the only kiter , don't worry finding a girl to help you raise your "thing" shouldn't be too difficult....
Titix, I just returned from a week in Cuba too: 4 days of good wind (15 to 20 knots). Stayed at resort in Cayo Guillermo: beautiful water, white sand beach & great conditions for kiting - there are large areas where the water is anything from a few inches to a metre deep.
Not sure, but it seemed to me the wind was probably frontal rather than the trades. As far as Cuba being really windy, I think you would need a lot more experience to properly judge that. The keys around Cayo Coco are certainly very beautiful & with your own transportation there would be hundreds of square kilometres of emerald green, shallow water to explore for kiting.
Sorry,as far as experience is concerned I lived in the Caribbean for many years. I have been almost everywhere and lived in many different areas.I was one of the first to windsurf in Marguerita (1986) before it became very popular, I started one the first schools in Cabarete(1988)and lived in Porto rico, Guadeloupe..... Southern Caribbean (Marguerita, Aruba,Curacao.. seem to be the windiest along with Cuba though conditions are quite different, drier subject to steady trade winds . Trade winds doesn't really blow in northern Cuba (temperature can sometimes drop to 15 degrees in winter because of its exposition to cold fronts). Southern Cuba (guardalavaca, banes) are more exposed to trade winds and its climate is more tropical much more like the north coast of the Dominican Republic.
Cayo coco and cayo Guillermo are very nice spots but you don't learn anything about Cuba since as most Cayos in Cuba it is very expensive and few Cubans are allowed to enter
it is only made for tourists. This year I went to Cayo Santa Maria, same story.
I try to be as precise and honest as possible because we read so many bullshit commercial-oriented articles. I believe it is the goal of such a forum to encourage this attitude. I am rather interested in surfing backpacking trips. Cancun, and even Hawaii is no surprise for me, nothing there in the people, in the culture will really teach you something you don't know. Cuba, for its history its rather peculiar, unamericanized type of society, its people,the friendliest in the region, its culture, is a disconcerting, confusing "trip".
About Cuba I have been there 4 times always in winter each time between 2 and 4 weeks but I have friends in Playa del este near Havana who have been giving me infos. I don't have experience of the summer there eventhough I heard of thermal northeast wind in Playa del este and Varadero and Guardalavaca near Holguin in those months and supposedly some southeast wind on the Caribbean coast around Cienfuegos, Playa Larga and Trinidad.