My wife and I did this several years back, New York to Chicago to San Francisco, and it really was a wonderful experience. But get a sleeper compartment, don't sit with the cattle. It's worth it, really. And that's even though we spent little time in our compartment almost the whole trip we were up in the observation car watching the American landscape roll by. One highlight of the trip was when storms over Helper, U…
> While waiting, there was a guy with a guitar in the observation car, and we had a nice sing-along. That bit sounds like hell to me but I'm glad you had fun! In the UK we have special carriages where you're not allowed to make a noise so you can avoid that kind of thing.
I personally think a well-executed acoustic guitar singalong can add a lot of real joy to any group experience.
I've played in rock bands since I was 15 (I'm north of 50 now), and I've been on stage in front of a thousand people and I've played to killer mosh pits and all that, but my best memories of all those years were the after-parties where it was just me and my bassist with acoustics and a room full of drunk people singing along to the Eagles or Sublime or maybe even Weezer...
Now, it helps to have a professional level acoustic guitar and, of course, a professional lead singer to hide everyone's mistakes, but it can be a magical, cathartic experience when the room all sings at the top of their lungs...
Great memories.