Our visit to Santana Row was well timed - between two patches of rainy weather. The day was glorious. If you get there early enough in the day (before 11 am) there are few people around to bother you, and there are plenty of benches and outdoor cafe seating where you can sit and unobtrusively draw your surroundings.
Santana Row is an upscale shopping area with lots of designer stores. Despite what people say about Santana Row being fake and snobbish, I actually like it. It's an attractive, elegant area to walk around and you can actually walk from shop to shop in the sunny outdoors. It has some unusual shops too, one of my favorites is MaiDo, a Japanese stationery store. Sadly parking has become an issue there, most lots seem to be for valet parking only now, so get there early.
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