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SF because it's so tightly packed and diverse with gorgeous architecture and landmarks in quite a few parts. I think the other part of it is that it can be fairly busy year-round without as much of a lull during the winter months as many of the other cities mentioned. Of course, that fog can come at many times of the year and is chilling, but goshdarn it's pretty.
I am leaning toward San Francisco for number 2. But, I could see a case be made for Chicago. SF just has more of the tight packed density that I like.
Philly and Boston are are also pretty interesting, they just seem a little less developed than SF where you have DT Union Square/Chinatown/Tenderloin, and then North Beach, Haight-Ashbery, Castro, Mission District, Marina District, Union Street, Filmore Street, etc.
Do you mean the narrow streets or the actual population? Chicago northside down the lake is denser than SF population wise...I don't think it has quite the pockets like Chinatown though that are in the 100K range. Chicago doesn't have the ultra narrow streets to the extent of SF has or even Philly, so I could see where that effect could be achieved on the street with more people getting packed through certain arteries.
1. NY
an amazing and unbelievable giant gap
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2. Chicago
3. SF
4. Philly
5. DC
6. Boston
gap
7. Baltimore
8. Seattle
9. New Orleans
10. Can't really think of a 10th city. I only kept it exclusively major.
However, let me give a shoutout to Old Town Alexandria, Virginia. Very impressive on the street.
Gap is a little too big. more like
1. New York city
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2. Chicago.
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Chicago and New York City
