While train travel provides a lot of benefits from my point of view, it carries a unique set of challenges. And they are things that can bite you hard if you don't realize them ahead of time and plan around them.
I've been the one stuck outside the Buffalo, NY train station in the dark of night, 30 degrees with a strong north wind and mist falling. I've been the one who took a bus from Vancouver to Seattle, then had to get to the train station with my luggage through a neighborhood that made me feel uncomfortable.
Challenges specific to this trip
- Early morning departure and arrival in Newton, KS. We're not talking the crack of dawn, either. The eastbound and westbound Southwest Chief trains meet not far east or west of Newton, depending on how late either train is running. Their stops are scheduled in the window between 1:45 and 3:15 a.m.
Can't do anything about that, and since the car is going to stay there in the parking lot while we're gone, I don't consider it a big deal. - Upside-down day in Buffalo. The train from Toronto arrives at 1 p.m. The train to Chicago departs at 12:30 a.m. The Buffalo/De Pew train station is small and inconveniently located. Definitely not walking distance to a restaurant or anything to do.
But guess what? It's reasonably close to the airport. My solution: an airport-area hotel. But wait... There's still transportation to the hotel, and checking in early, and checking out when they're barely finishing check-in for the night.
Research to the rescue, and a phone call. Research: find a hotel with an airport shuttle. Verify the shuttle will go to the train station on demand. The hotel doesn't offer day rates, but they do offer early check-in. The shuttle runs all day and all night. The phone call: it was something I do anyway — for both myself and my travelers. I call to verify the hotel's computer shows the reservation I show in the agency booking system. While I was confirming that, I also discussed the logistics.
How to minimize the wait time for the shuttle? Call the front desk as we arrive at Exchange Place, giving them 20-30 minutes to get the shuttle to swing by De Pew worked into their next airport run. Early check-in? No problem; the room record is noted with the reason, they'll have a room ready by 1:30. Depart at 11 p.m. to be at the train station with time to spare? No problem, but remind them day-of. Easy-peasy.
So really, the only thing not taken care of is a meal while we're there. Can anyone say hotel delivery? - What if the train is late? My hard and fast rule: regardless of whether I'm driving, flying, or taking the train, I always arrive at least one day before departure. That buffer should take care of it. We're scheduled in at 8:45 p.m., check-in time is 11 a.m. So even a significant late arrival only cuts our time in the hotel.
Joys specific to this trip
- Spectacular scenery in parts of the continent I've never seen. The Ohio River Valley east of Cincinnati after sunrise. The New River Gorge in West Virginia, said to be the best scenery along the rail in the entire eastern seaboard. The Shenandoah and Appalachians. The St. Lawrence River Valley. Niagara Falls.
Some of these I've seen from the highway. But driving and getting to ride and thoroughly enjoy the scenery is a totally different experience. - The similar, yet different experiences of sleeping on Superliner vs. Viewliner rolling stock. The train set east of Chicago can't be tall due to the tunnels getting to New York City's Penn Station. So Viewliners aren't much larger than subway cars. While Superliners, used west of Chicago, are closer in size to the car-carrier trailers or maybe 2/3 the height of a double-stack intermodal trailer/shipping box car. I've been on both, multiple times, and they are different experiences. I'm looking forward to sharing them in real time.
- The similar, yet different, experiences of riding Amtrak and ViaRail. I don't know what to expect here, but I imagine procedures will be different, the ride will be different, and ... well, I guess I have to wait and see. ViaRail doesn't run sleeper cars on this service, so we will be in coach seats; that's fine, these are short hops in train time. I think the longest we're on the train is a little over 4 hours.
Oh, yeah ... no airports, no TSA lines, and if we're late, we still get fed.

Closed circuit for those using Uber at some point: schedule it in advance.
We have 4 Uber legs this trip: 30th St Station in Philadelphia to our hotel, hotel to the ship, and back and forth between the Toronto train station and our hotel. All four are already booked, I did that last week. If the train is late, I can reschedule the Uber up to an hour before the original pickup time. And I'll certainly know it well ahead of that, so no worries there.