I love Amtrak! I wish more people would take it so it gets more funds for improvement and expanded train frequencies/locations. I regularly take the Hiawatha from Chicago to Milwaukee. That’s a short commuter train (1.15 hours) and is fantastic. It runs every couple couples and is almost always on time and has WiFi. Even the car centric in-laws have started to take it to visit us instead of driving down, because they realized how much more relaxing it is and that it’s a wash with tolls+fuel+parking. I’ve taken the Boston to NYC commuter train (slow one not Acela) a few times and I enjoyed that one too.
I also frequently take the long distance empire builder but only from Chicago to LaCrosse WI (about 5 hours when on time). That train is always late. It’s usually on time leaving Chicago, but a couple hours late coming back from the west coast because it’s more effected by weather and freight traffic. Sometimes it’s very, very late like 5+ hours. Last trip had a major snowstorm and I was 16 hours late, supposed to arrive 5pm and got in at 9:15 am. There was a train derailment + two 20+ car pile ups on the interstate that prevented to freight train crew from pulling the derailed train off the track. To be fair both the interstate and highway was closed, so it’s not like a car could have got me to Chicago any faster and definitely not any safer. Plus side when it’s that late you get free food and can call Amtrack to have them refund your entire trip (not just that leg). I still take and recommend the train to LaCrosse over driving because it’s cheaper (than renting a car, paying tolls and fuel), I hate driving, and it’s much more relaxing way to travel. But lesson is never do long distance Amtrack when you’re in a time crunch or need to be somewhere at specific times. Give yourself an extra day, where you don’t plan on anything the day after you arrive, so your not stressed about missed reservations.
The empire builder has a great observatory car that I love, snack counter, and dining car. Snack food is typical concession stand type food and fine, dining car food with overpriced mediocre food. Pro-tip you can bring your own food and beverages (including adult) and eat/drink them in observatory car. For long distance, I’ve tried the sleeper car once when it was randomly cheaper than seats. It was a roomette and tiny. I think the beds would be nice for overnights. I’ve slept over night in coach twice, which is rough but doable. The coach seats are roomy and recline a lot with footrests, plus plenty of space between seats. But you can’t lay flat so it’s still uncomfortable to sleep. If you do a roomette pack your carry ons (one each) light and in squishable backpacks or duffle bags, because they go under your seats and not a ton of room. There’s more room for baggage in coach oddly enough. I’ve never checked bags so can’t speak to that process. No WiFi on long distance trains. And yeah very wierd hours for stops at certain places and only one train a day, so you better not miss it!
I wouldn’t do the packages though personally, because I like to do my own thing and it’s usually cheaper to books things independently. Just buy the train tickets through Amtrak online then look for hotels separately. Note that long distance trains the prices go up the closer to departure date. You can book almost a year in advance and the earlier you book long distance the cheaper it will be (sometimes $200+ different for my 5 hour train ride). For our Milwaukee-chicago commuter Amtrak train, the prices are always the same (or differ by literally $2) no matter when you book, 1 year or 1 hour in advance.
In short, if you have time to take the train it’s great and eco-friendly, so do it! If you don’t have much time, it’ll stress you out (unless you’re taking the short commuter trains that have good on-time rates). I plan on doing the long distance trains to travel to the national parks someday when I have more vacation time.
