The train trip I took with my family in high school. We went to Houston, Texas from the CA Bay Area and, well, maybe it didn't take 2 weeks to get there, but it felt like it. The sleeper 'rooms' were like coffins. In the evenings they would play movies in one of the more open cars and it was so crowded you could barely see the screen (but it was okay because they just played Armageddon over and over). During the trip there was a train accident in Chicago so they were being uber careful i.e. slow as hell.
When we got to Houston, well, we were there to visit my great-grandmother, so use your imagination. Old-person smelling house. The highlight of the experience was fixing her washing machine. Nearby lived the stereotypical crazy great aunt with 2 dozen cats (my brother got ringworm). Excessive boredom. Oh, and it was humid. The only 'thing' we did was going to the space center, which was okay.
Then we had to get back home. The train was so slow that we missed our connection and had to take a bus to catch up. We were on there for hours and they wouldn't stop so we could get food. When we finally caught up with our train there was some problem with restocking and all they could give us was a cup of juice for the rest of the trip. And people wonder why Amtrak has been getting bailouts from the government for years.