The crunchy areas tend to be more urban. Port Washington is a lovely little place, but it's a little far from Milwaukee proper (for me anyway!) and I couldn't tell you how crunchy it is, my uneducated guess is not very.
Bayview certainly has a big crunch factor and is family friendly. If it wasn't for DH/my job further west, we'd probably live there, although we really like where we live too, which is Wauwatosa. I wouldn't call it a hotbed of crunchy, per se, but it has a fairly diverse population, especially on the eastern half and has lots to do. It has a more suburban feel to it but still has the perks of being urban as well. Shorewood would be another similar suburb. However, if you're not going to use the public school system, I'm not sure I'd justify the higher taxes, you know? I've heard great things about Tamarack Waldorf, which is on the East side. There's also a Waldorf school out in the western suburbs, as you probably know, Prairie Hill. The county surrounding it is very, very conservative and traditional. You would probably have to look a bit harder for nearby like-minded people. They certainly exist, just not in the numbers you'd see closer in to Milwaukee. My friend (who is also here on Mothering, maybe she'll chime in) lives in Brown Deer - very affordable and more suburban in style. I wouldn't call it crunchy, but it's not far away to areas that are.
I'll watch this thread. I don't know if any of that helped, but if you have any more questions, feel free! I'm sure others will chime in too, there's quite a few of us Milwaukeeans here. :)