Personally, I love the area around California. It's hot, but not sticky like Florida as the humidity is nice and low. I grew up in a beach suburb of LA (Manhattan Beach), but left before I was 10 and now can't wait to go back and do some flying!
I've been told that flying in northern cali is pretty amazing too, the bay area being spectacular with mountains, fertile valleys (Napa Valley!) and the deserts of the wild west close by, with some settlements to match
Chris, I don't know much about Westwind, but I do remember from camping out in Arizona when I was a kid that it's a pretty massive wilderness. There's not much except desert (though not as bad as Texas). Not so great for local flying if you like the eye candy while you practice, but still some great oppotunities for cross country.