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Museums, pre-1800's architecture, quaint eateries, and a walking city

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If this describes a trip you have taken, please tell me about it.
I am looking for an idea of where to go for about one week. Oh, another requirement, this place needs to have summer time temperatures that don't often exceed the upper 70's (F) with low humidity.
I like to eat outside where one can "people watch". If this place has easy access to trains which would permit a round trip one or two day trip to mountains with scenery, that would enhance my stay.
Budget is moderate. I live in the United States.

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