Hi
Well, yes... im from Azores (ut i live in Lisbon)... but i have also some knoledge about Madeira as well...
In Madeira if u are not a beginner, u have the Stª Cruz spot near the airport, or if u like rocks and waves try the North side.
About Porto Santo island, you have nice wind , nice weather (all year) and nice water cº...
the wind is off-shore....
In Azores, there is 9 islands
... but u can find some sand in Faial, S. Miguel, Terceira and Santa Maria... if u are a pro, u can ride in the ocean and maybe find some dolphins... supe nice... believe me
Madeira and Azores are not the best spot for kitesurf beginners, but with some luck... advanced kitesurfers will have great fun... oh!!! and must try S. Jorge waves... (and rocks too.. lol) ...
take care...