My initial thought is that it will take 3-4 days to see Boston stuff and 3 days to see NYC stuff. We can arrange it in any order you want, but I think it might be best to do two days in Boston (Sunday and Monday), three days in NYC (Tuesday-Thursday), and then another two days in Boston (Friday and Saturday). I am planning on taking those days off, and Claire will have some days off of school, but probably not all days.
The two activities I have heard are:
In our experience, you can only do one big activity per day in NYC, and a play and the Statue of Liberty both count as big activities. My recommendation is that we travel to NYC on a morning via the New Haven train line and travel back to Fitchburg on an afternoon. This gives us time to fit in two big activities.
We should have a food plan so we aren’t stuck trying to decide what to do on a crowded street corner in NYC. My preference is to hit the various ethnic foods in NYC. There is:
Renting a house may be the best lodging option - Jeri found a range from $300-600 per night for a house that sleeps 10 or more people. Hotels will cost more for 10 people (very small rooms means 4 to a room at the maximum, so we would need to rent 4 hotel rooms. The best price I have ever seen for a decent (not bed bugs, etc.) hotel in NYC recently is $150 per room per night, so a house might make more sense.