I am looking into a trip from the East Coast to California, and my first destination in the state would be to visit my friend nearby Los Angeles.
I am planning to travel from Los Angeles via Seattle in one direction, taking the Empire builder and probably breaking some time in Seattle, so my first question is which direction should I do it in? I know this has been asked enough times to solve the economic crisis if we got a dollar each time, but it would be nice for you to clarify the consensus for me.
Which direction your loop should go depends in large part on which trains you want to take and in smaller part on what time of year you'll be taking them. Summer means longer daylight hours and thus more of any given route's scenery will be visible, so as a general rule summer is better
Though traveling through snowfall is pretty cool! Then again, I traveled through a blizzard on the Empire Builder in June this year, so this all follows the general rule that "on Amtrak, nothing is predictable!" :lol:
On the Coast Starlight, northbound the best coastal stretches will be in daylight while southbound it's less of a guarantee. On the Empire Builder, eastbound Glacier National Park will be in daylight while westbound it's less of a guarantee (but in late spring and summer, it's reasonably likely; this train has good timekeeping as a general rule, and even in late April it was daylight throughout the park).
If you take the California Zephyr, westbound the Rockies will be in daylight while eastbound it's less of a guarantee. I'm not sure of the best direction for the Southwest Chief or Sunset Limited, but I will say that I think of these three trains, the Sunset Limited has the least exciting scenery. (Ask me again in a month; I'm thinking of taking it in November!) The Rockies are magnificent.
My second regards the other directions. Leaving from Washington Union Station, I'm given, as I'm sure you all will already have worked out, four options taking varying lengths of time; taking the Crescent and the Sunset Limited with a night in New Orleans; or traveling via Chicago either on the Cardinal or the Capitol Limited (although I would then have to go via Chicago both ways!) and taking the Texas Eagle, the Southwest Chief, or, with a longer journey, the California Zephyr via Northern California.
The Crescent is dear to my heart, being my "hometown train" (growing up in central Virginia), and I enjoyed riding to New Orleans and back. But it's a much longer route to the west coast, especially with a required one (or two) night layover in New Orleans. On the other hand, New Orleans is a marvelous city and well worth the visit if you can afford it. But you have to consider that. And then, of course, you're committed to the Sunset Limited, which may not be the best scenery between the Midwest and the West.
Also, while New Orleans is fantastic, you have to factor in the additional cost of a hotel for a night (or two). I say "or two" because as you've probably noticed, the Sunset Limited only runs three days a week instead of daily, so if you arrive in New Orleans on the Crescent on certain days, the Sunset Limited will depart the next day, while on other days, you'll have to wait an extra day. Obviously, you can adjust your dates to make this work with whichever layover you choose.
In Chicago going westbound (and eastbound), you won't have any problems with a same-day connection because the California Zephyr, Southwest Chief, and Empire Builder all run daily. The three or four hour layover in Chicago is nice, since it's right around lunchtime and there are lots of places you can walk to from Chicago Union Station. It's only two blocks from the heart of Chicago ("the Loop"). Deep dish pizza from Giordano's is a favorite of many people on this forum
You should also ride the El (you can purchase a day pass in Chicago Union Station, in the luggage locker room--and you can rent a luggage locker for your carry-on bags for a few dollars, too)--it's sort of a cross between "public transit" and "roller coaster", and it's a real Chicago experience.
The Cardinal has the great scenery of the Appalachians and the New River Gorge, which are most likely to be in daylight going westbound. The Capitol Limited has a shorter window of marvelous scenery in Virginia and West Virginia. The other difference between these three eastern trains is that the Capitol Limited uses Superliner (double-decker) cars--which all of the western trains use--while the Cardinal and Crescent use Amfleet (single-level) cars. And a third difference is that the Capitol Limited and Crescent both offer a much higher quality of food as compared to the Cardinal, and of those two, the Crescent has more seating in the dining car (so it's less likely you'll be told you can't get a dinner reservation). All of these trains also carry a "cafe car" in addition, which are all basically the same (where you can get microwaved burgers and hot dogs but not actual sit-down restaurant meals).
Note that like the Sunset Limited, the Cardinal also only runs three days a week. So again, if you're taking it, you should plan accordingly if you don't want to spend a night in Chicago. The Capitol Limited and Lake Shore Limited are daily, so a same-day connection is not a problem.
And your other option for a return from Chicago to the East Coast is the Lake Shore Limited (to New York), followed by a Regional south from New York. This is actually a fantastic option, as the Hudson River Valley is spectacular, and it will be in daylight splendor going eastbound from Chicago (well, once the train is going "due south" from Albany instead of "east", of course!). Here again, you'll be on single-level cars and have the least desirable sort of dining car, but the scenery is worth it in my opinion.
And in the case of routes which the Amtrak website would not immediately come up with on an end-to-end journey search, e.g. Los Angeles - Seattle - Chicago - New York, are there any particular tips or tricks on how to force Amtrak's website to give you the schedule that you want, for example splitting your booking into two parts at on obscure intermediate station? Or, indeed, would such bookings be easier for a representative on the phone to make with your instructions, rather than doing it yourself on the internet?
You don't have to book your entire trip as a single booking. You could try to (as it sounds like you did) use the "multi-city" option to do this, but there's no advantage over booking each leg of your trip separately--there's no price savings by combining legs. So you should book "east coast to west coast" as a single booking (e.g., WAS to LAX), "west coast" (e.g., LAX to SEA), and "west coast to east coast" (e.g., SEA to WAS) separately. That eliminates the problem you were having.
But it
is advisable to book "east coast to west coast" as a single reservation and "west coast to east coast" likeise (each of which will be two trains) together--that way (and only that way) you'll have a "guaranteed connection", which means that if your first train is late, it is Amtrak's responsibility to get you to your final destination. If that requires booking you on a different train, that's no additional cost to you; if that requires you to spend a night in Chicago, that's no additional cost to you.
Fourthly, on the Empire builder and whatever other route you recommend, what would be the best side of the train to travel on to enjoy the scenery the most?
Generally speaking, for
most trains both sides have good views about the same amount of the time--though on the Coast Starlight obviously only the western side has the Pacific Ocean, which makes a
huge difference between the two sides
For the Empire Builder, California Zephyr, Coast Starlight, etc, there is a lounge car open to all with enormous windows on both sides which wrap up to the ceiling. You're free to move from your coach (or roomette) seat into the lounge at any time for the best views (though for the Rockies, Glacier National Park, etc, it can get pretty full). As far as which side of the car your coach seat or roomette is on, you won't have a choice most of the time, though for some stretches the train may be empty enough that you can dash over to the other side of the coach car for a look if you spot something interesting over there. The river is on the left side (going west) on the California Zephyr while I think there were more mountains on the right side (again, going west); but really, both sides were grand, and if you're in the lounge you can see both sides. I think the best New River Gorge scenery is on the right (going east) on the Cardinal, and the Hudson River is on the right (going east/south) on the Lake Shore Limited. Being single-level trains, neither have the observation-lounge car (though you can always go to the cafe car and sit anywhere).
And lastly, if I was rationing my roomette use to just one leg out of the two or three for the sake of saving money, what would be the best way to go about it to minimise suffering while keeping costs reasonable?
Perhaps the biggest factor here, since cost is an issue, is "which segment can you get the cheapest roomette". Roomette costs can vary tremendously, even over equivalent distances, because they're priced on a bucket system where the cost is inversely proportional to the number of remaining available roomettes. That is, when they're almost all sold out, they're really expensive ($400+/night), but if there are a lot of them available, they can be really cheap ($150+/night). Those are really rough numbers, but just to give you an idea.
As a general rule, a roomette will leave you well-rested upon arrival, so another consideration is "do you really need to be well-rested when you arrive home and can immediately go to sleep in your own bed" as opposed to "would you rather be well-rested when you arrive somewhere you're visiting for a limited amount of time". That is, you might prefer the roomette prior to visiting Los Angeles or Seattle. On the other hand, if you have to go to work the morning after you get home, you might want the roomette prior to that, especially since you'll be well-rested right before you start the entire vacation and you'll have "general travel weariness" by the return....
Remember also that your dining car meals are free for the time you have a roomette. So, for instance, you might value a roomette less on the Cardinal or Lake Shore Limited, where the dining car is inferior (and the menu for the "free meal" will consist of things like pasta or a chicken sandwich or the equivalent, as opposed to a menu offering steak or fish filet or several other excellent choices on all the other trains you're considering).
Oh, and one final perk from having a roomette is that if you arrive in or depart from (doesn't have to be both) Chicago in a roomette on a given day, you are permitted to use the "Metropolitan Lounge" for that day. It's a more relaxing place than the main waiting room, but perhaps more importantly for you, you can leave your carry-on bags there for free (they'll be watched) instead of paying for a luggage locker at the station. Of course, your laptop will be more secure in the locker than in the lounge (where it's watched but not actually locked up). Still, it's a nice perk.
If you are checking any baggage from Washington (or New York) to Los Angeles or Seattle to Washington (or New York), you don't have to handle it in Chicago (or New Orleans) when you change trains. It will be checked through, regardless of whether you have a roomette at any point. It's just carry-on bags that you'll have to consider a locker (or the lounge) for.
There are really no "bad options" here--these are all wonderful trains. But there are certainly differences (as you know), and certain routes might be much more appealing to you than others. Hopefully this helps you decide! Others will chime in I'm sure, and everyone here is happy to answer your questions and offer (perhaps too much!) advice