Good question but tricksy one. You can have a look at several articles in http://www.iksurfmag.com
" onclick="window.open(this.href);return false; (or other online mags) that they have done about travelling & kite surfing on different back issues. They do not go too much in detail but you can get the general idea of a spot. Or you can check the past wind records in previous years of different spots in websites like http://www.windguru.com
" onclick="window.open(this.href);return false;. Then consult with a travel agent or even look online because some (but not many) resorts are not open all year round.
And after you have done all that as an extra precaution you could just book last minute so that you can check the forecast for the week that you will be goind. (It would be really bad luck to go to some nice and warm tropical place and then it's windy but raining 4 out of 7 days)
In any case, have fun and let us know how it was when you come back!!!