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San Francisco. At the core of the urban areas (downtown and neighborhoods immediately adjacent), I don't think you can really tell which is bigger just by look or feel. Both are very dense and compact (not to mention, picturesque).
However, outside of the urban core, the San Francisco Bay Area remains more "urban" for a longer ways than Boston. I think geography plays a big role. The San Francisco Peninsula is surrounded by water on all three sides, and has a pretty large mountain range forming a "spine" on it. Even the East Bay and North Bay only have relatively small slivers of land that are suitable for building between the mountains and the water. This forces development (even suburban development) to be much denser in nature.
On the other hand Boston sort of dissolves into a lower density sprawl outside of the core. Unlike San Francisco/the Bay Area where growth is restricted by mountains and water, Boston suburbs can spread outward almost uninhibited to the North, West, and South of the urban core.
I think the cores of each principal city (Boston and San Francisco) are similar in their "urbanity." However, I think the exterior portions of San Francisco and its suburbs are far more urban than metro Boston.
How did SF win? That's stupid. Have any Californians actually BEEN OUT to Boston?
Yes I have.
Whats more stupid is the fact that you admit to never being west of Chicago but act as if you know the answer. Just because you're not well traveled doesn't mean we all are.
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