re: Cities that are surprisingly beautiful

Sausalito's pretty small for a city though. I've driven through hundreds of times and only stopped maybe 5 times? There's not much there unless you like yuppies and over priced restaurants.

For cities over 100k population, I nominate Santa Rosa CA, about an hour north of Sausalito. It's in a valley surrounded by mountains and only 40 minutes from the coast. Vineyards everywhere and still has some pretty historic buildings downtown. The food scene is pretty great too.