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For Boston:
Kenmore Square has a lot of clubs/bars in the area. Boston College, Boston University and Northeastern University are in that area as well as Fenway Park.
The parks downtown (Boston Common and Public Gardens) I never found to be terribly interesting but are nice to walk through that time of year.
The typical touristy things are the Freedom Trail (walking tour) Fanuil Hall/Quincy Market (outdoor mall) and the Duck Tours (land/water tour).
There is a new contemporary art museum on the waterfront, not far from the aquarium.
Most of the neighborhoods have been gentrified but the North End is still mostly Italian, South Boston is mostly Irish, and Back Bay/Beacon Hill is money. There is a small Chinatown area as well. Parts of Roxbury and Mattapan are the seedier areas.
Harvard Square, across the river in Cambridge, can be an interesting place to walk around and people watch.
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