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For a larger city, I'd say Boston overall. Honolulu would also rank highly, based largely on the weather and the scenery and some fairly limited tourist areas, such as Waikiki. (Large parts of Honolulu are rather run-down and are not in the least bit appealing.) I'd also rank Denver pretty high on this list. (I know that a lot of people really like Austin, but since I've never been there, I can't comment on that.)
For a smaller city, I'd say Annapolis.
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