My first post, and it is a bad review...
We just got back from a train trip to Disney. NY to Kissimmee. My Mom and Dad went with us, and Dad doesn't fly, so we decided to take the train. The first part of the ride was lovely, scenic upstate NY. Train was a bit on the older side, but not bad at all. Then the switch over in NYC.
I may have had two bad trains, but we will never go that route again. The bathrooms became extremely dirty as the trip progressed. We had three people get taken off the train on the way down, and two taken off on the way back home, in handcuffs no less. There is alcohol served on the train, and those taken off had been drinking a lot. Which come to think of it, is probably why the bathrooms get so messy. The dining car meal for a family of five with tip was $75. And the food was neither plentiful, or good.
Best advice. Sit in the middle of the car, if you can. It gets very cold by the adjoining doors between two cars if you are going down during the winter months. Bring a light sheet to cover up with. They provide a small travel size pillow, you may want to pick up a couple of small pillows though, as the seats aren't always very comfy. Bring lots of snacks, and water, and try to avoid the snack and dining cars. Water is $2 a bottle, sodas $1.75, candy bars and chips around $2 a piece. The layover in NYC is probably the best place to get something to eat. Don't count on getting in the lounge car if the train is full, and if you do, be prepared for the drinkers, they usually congregate there.
ETA: Handheld games are great. And I don't mean gameboys, though they are good. We brought Yahtzee, Poker, Hangman. It gave everyone something they could do in their seats. Also, a portable dvd player. There are outlets in most of the seats, so you can plug in, and watch a movie. Our train down was stricter about noise than the train back, so head phones are a good idea.
There were a few highlights. You can see quite a bit when you go through DC. The view of Washington Memorial at night is wonderful. On the trip down to the city you can see Westpoint Academy. If the other option is driving, I would still go for the train. It is quicker, and you don't need to stop everytime someone needs to use the bathroom. And, most rest stops bathrooms aren't very clean, so the trains messy bathrooms aren't a deterent there.
We are flying next time, and anyone who wants to go that doesn't fly, can get there however they want.