Thx to Titix for providing his opinion:
Let me sum up what I said: 3 criteria for me; wind conditions for kitesurfing,space,price once you are there included transportation,cultural aspects.
In SEPT/OCT/NOV/ Marguerita In the Caribbean,
Corsica (where I am from originally, the best of all!)Sardegna and Tarifa in Europe,
Jan, Feb,March,April consider Barbados, Roques, Porto rico, Cuba (eventhough you may depend on transportation)