For Spots look on www.splocs.com
In think Aruba would be your best bet for wind!
But I would decide spontaneously and look at forecasts then book a flight.
Also check Cartagena, Colombia, since it might have good winds and it a beautiful city, you lady would like it. Direct flights from Miami available.
I'm considering visiting Colombia in July, is that good time for wind around Cartagena ?
how safe is it to travel in rental car to kite beaches
In wouldn't worry about safety. I never did, always felt safe.
July is not good for wind in Cartagena. You have to go all the way east to the Cabo for wind.
But July is great for winds in San Andres Island!
Most beautiful spot I have seen so far...great flat water!
Belongs to Colombia bits sits 800km off the coast to the North from Colombia.
Direct flights from Canada, Bogota, Cartagena.
for more info and pictures!