ZDG- I've been following this thread with much interest. I too have been california dreaming for sometime now, but my circumstances are different. I live in Mclean, Va and my kids are in a fantastic school district, so I don't want to make any move until they are in college. That time will come in 4 short years when my youngest will head off to college. I am FI already but continue to keep my dental practice running because I love what I do. I am a conservative christian but not sure if that would make much of a difference in where I choose to live. My biggest obstacle to moving west will be leaving my aging parents behind here in the DC area- that might trump everything.
So what was it about Santa Rosa that made it the "place"?
Well, it's funny you should ask. I wouldn't tell anyone that I think Santa Rosa is really the "perfect place" or anything, as we sort of circled in to it.
I really wanted to move to Sonoma itself (the city, not just the county). We spent what was supposed to be 4 days, which turned into 8 days, which turned into 11 days in the Wine Country. Here's how our thought process worked:
When we first arrived, we got a hotel in Petaluma, mostly out of financial reasons (we had a free room at the Sheraton there) and the fact that all the towns/cities of the Wine Country are a short drive away. Petaluma seemed cool enough, but isn't really what most people are thinking when they think Wine Country visually. The first thing we became aware of instantly was the weather. It was absolutely gorgeous, with the exception of the constant wind right on the marina in Petaluma (which turned out to be a localized problem; thankfully). It was cool and humid enough in the mornings and absolutely perfect in the afternoons, with highs in the mid 80s but no humidity whatsoever so that if you were in the shade, the constant cool breeze keeps it perfectly pleasant from about 10am until 6pm.
The second town we checked out was Santa Rosa, which is the largest "city" in Sonoma County. It definitely had the most city feel of all the towns, but don't let that fool you. There's only about 170,000 people there and it definitely feels like a very, very small city; but in a good way. The terrain is completely different than the rest of the towns we visited in that there are pine/fir trees and it feels more like a mountain resort town than the hills upon hills of vines you were expecting to see. Not that there aren't a ton of vineyard lined hills, but in the middle of the city, you won't see them.
Then we checked out Napa (city). While downtown Napa seems very cool, it wasn't at all what we were expecting. There's a lot more in terms of high-end food, but also an obscene amount of tourists. Not that we weren't expecting that part of it, I just didn't quite expect it to basically be Wine Disneyland. Napa really wasn't for us, but I can see why it is for a lot of people.
Finally, we went to Sonoma (city). I loved it. We walked the Plaza multiple times, ate at a number of the restaurants right around there, and spent a lot of time just relaxing with some wine. It was just fantastic. Every afternoon we spent in Sonoma, I felt like I could spend the rest of my life there. We looked at houses within walking distance from the Plaza and found the bang-for-buck to be a little underwhelming. We found some nice houses, sure, but in about the same price range as what we'd see in Manhattan. Ultimately, we realized the school situation in Sonoma was going to keep us from moving there (there's no progressive high school of any kind in Sonoma).
So, after all that, we ended up choosing Santa Rosa because we found a stunning house on the side of a hill with a view of what looks like Italy and that has fantastic schools. I definitely preferred the lifestyle in Sonoma and probably would have liked the scenery of Healdsburg (which we spent no appreciable time in) more, but Santa Rosa had the best mix of what we wanted and is of course within driving range of all those other places for weekend jaunts.
