When I read stories like this I just have to laugh, as they're so different from my own experience.
I left for West Point in the days of regulated airline fares; if I recall correctly, it cost more to fly from Sacramento to New York back then than it does today! Anyway, there was never any thought about any of my family going with me--no, a handful of family members took me to the airport, we said good-bye at the gate (anyone could go to the gate in those days), and off I went. On my own. With one suitcase. And that was that.
I got to New York and stayed in a hotel near Central Park. That hotel had a package deal for incoming cadets, and I was roomed with a classmate from the US Virgin Islands. We took a bus tour of NYC (I only remember St. Patrick's Cathedral and Wall Street), and later than night my roomie and I went out for a "final" dinner and dessert. There was a huge tub in the bathroom, and I took a long, hot soak before going to bed.
The hotel filled a couple of buses with incoming cadets the next morning, and maybe 90 minutes later we arrived at the West Point football stadium--where I was surprised to see others with their parents. Honestly, it had never even occurred to me to have family accompany me there.