Make sure you try currywurst in Germany. It's basically a hot dog with tomato sauce (ketchup) and curry powder. Tastes brilliant and only costs 1 or 2 Euro.
The trolley tour of Boston, offered as an optional, is the best way to see the entire city. Take it at your own pace, but I would suggest stopping off at the USS Constitution and Fenway.
For ladies I would definitely recommend finding some slightly nicer than normal black flats... I bought some in Prague for super cheap and still wear them all the time!