I did SF to NY back in my 20s after working at summer camp. Not in one go, but over about four weeks with stops in Last Vegas, San Diego, New Orleans and Miami.

I did SF to NY back in my 20s after working at summer camp. Not in one go, but over about four weeks with stops in Last Vegas, San Diego, New Orleans and Miami. It was a great experience and I met some great people. Never had a sleeper, and that just made it easier to mingle with my fellow travellers. I remember playing hours of chess with some old dude in the smoking carriage, and the shitty cans of margaritas at happy hour served from the train bar. Unlike jumping on the plane, the train journeys were an integral part of the travelling experience, rather than just a method of getting from one city to another.