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First time trip to NYC

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My 14 year old wants to take a trip to NYC this summer. He and I will be driving in from the south part of the US. I'm planning on staying 4-5 days this coming June. Since I'm at the very beginning of my planning, I am open to any and all advice. I have so many questions!! (Should I drive into NYC? Should we stay downtown? Must-see things besides the obvious? Suggested itineraries? Should we stay outside of town where I can park my car and take the train into town?) Thanks for helping!

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