I have the chance to dedicate one week starting from the 24th of May this year to a kitesurfing vacation and I really need to have as many windy days as possible. The area I can consider is Caribbean/South America. I would really appreciate truly knowledgeable advices.
I would like to assure you that I have researched very carefully the web and the forum before posting this topic. Although there is a "Windy holiday destinations by month" topic, the information inside is limited or only partially correct. For example I asked a kitesurf instructor who has lived in Cabarete for years if the wind is reliable in May. She told me that May is actually not a reliable month for Cabarete and that the chance for wind is 50/50. She said that it's a month of transition and what happens is that some years there is a strong wind and some other years there is no wind AT ALL for 15-20 consecutive days. The great months there are June-July-August.
I would hang myself if I go there and I find 7 out of 7 no windy days or even 3-4 out of 7. So please let me know which are the really wind-reliable locations for the month of May.
Thank you in advance!