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Hard to choose between these two. I like both equally well. Boston is better in some aspects, Quebec City is better in others. Both cities are proud of their history, and have some fantastic sites to visit, both have good places to eat. Quebec tends to have a bit more attitude towards English speakers and Boston doesn't care what your native language is.
I still lean slightly toward Quebec City I think though. I know enough French to get by in stores and restaurants, and the old section of town is very walkable and quite nice really.
I really like Boston and am considering flying into Montreal and going on a roadtrip that would include Quebec City. It looks beautiful; I hope it is as enjoyable as Boston. I could do without the valet in Boston speaking of "pahk mah cah"
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