worked in Boracay for one season at Ocean Republic.
The best time for wind is late October up to late February/March. Fantastic place to spend christmass and new year. The place delivers insane partying (don't get too confused with the lady boys though, or you may have a serious hungover the day after, lol (but this is one place where you can end the night not remembering your name and no one will care!)), great wind through december and january, has loads of non-windy days options (from snorkelling, to mean frisbee games, dragon boat, diving, horse riding, cycling! (try to keep "getting drunk" for the evening tho or you won't keep up!)), offers the best lifestyle ever (Lobster every day), has some of the most gorgeous sunsets I've ever seen (sipping a pina colada after a kiting day: sweet as!), has a fantastic happy-laid back local crew, is dirt cheap, basically... it's as close as it gets from heaven on earth!
I truly recommmend the trip to anyone truly after a getaway, offering kiting with benefits!!!!
Do give it a shot, and do contact Glen at Ocean Republic on my behalf: he's one in a million sort of guy, he will look after all your bookings and even rent out equipment if you can't be bothered carrying yours, and you'll enjoy your stay with him all the way!

I live in Cebu in the Philippines for 6 months a year, go up to Boracay a few times for a week or so, great place to kite, great place to party, and yes see or get in contact with glen he is the man, will do you good deals on new kites too, is the agent for naish, north, Best and slingshot in the philippines.
Top end of Cebu around Santa Fe is also really good for kites, best in december to March but we have been getting some good wind the last few weeks from time to time.
If you want waves, try Siagao Island, or calicoan off Samar, have not kited there yet but go there surfing.
happy adventures!