When I was a junior in high school, two of my best friends and I went to NYC for spring break. We did musical theater together, and 2/3 of us hadn't seen a Broadway show, which was a sin. We spent four days doing/seeing/eating everything we could, and I've been itching to go back ever since.
Alas, my dad's old roommate lives just north of New York City -- and his sweet family invited us to stay with them! The Brocketts roadtripped up the East Coast, stopping in Charleston and Washington D.C. without managing to slit each other's throats. Just arriving in NYC was a success in our book.