Actually they are all legal, guaranteed connections, even Galesburg, which I verified by trying a OMA-ABQ trip and 6 to 3 at GBB is the routing it came up with. Your selected routes show up as options OLW-GBB and GBB-OLW on the website.I have worked up a schedule as follows: Depart OLY on Starlight to Sacramento; Zephyr to Galesburg; Galesburg to LAX; LAX to OLY. Should be a seamless ride except for the LAX connection to the Starlight.
How does one book these trains so that Amtrak is aware of my connections?
You could just do a simple round trip OLW (not OLY) - GBB, choosing the 11-6 OLW-SAC- GBB outbound routing and the 3-14 GBB-LAX-OLW routing on the return. With that said, I would still use Multi-City for the booking entering 2 segments, OLW-GBB and GBB-OLW rather than the simplified round trip option. The reason is that Multi-City just seems to have fewer weird glitches (like being unable to successfully mix accommodation types) and it also still gives you accommodation charge/rail fare breakdowns. You will generally want to enter the longest segments that will come up with a valid routing that you want.
Either method will give you one reservation number with all connections, which is the important thing when it comes to ensuring that your guaranteed connections are actually guaranteed.
The SAC connection is pretty safe. The GBB one is less so with the recent performance of 6. LAX 3-14 is risky these days. I do not know how Amtrak protects at Galesburg in case of a miss. Likely a hotel and a ticket on the next day's train. However they may not have a direct billing arrangement with hotels at Galesburg as they do at Chicago. You might have to pay for it yourself and send them the bill or they might just hand you enough cash at the ticket counter that they think should cover a hotel and send you on your way.
3-14 is typically protected by putting you on the much faster San Joaquin bus/train connection and catching you up to the Starlight at EMY, MTZ or SAC. Only if the SW Chief is so late that that option won't work will they lay you over for the next day's train.
Bear in mind that if you are laid over due to a missed connection and you are booked in a sleeper, a sleeper accommodation is not guaranteed for the next day's train. If no sleepers are available on your revised itinerary you will be downgraded to coach with your accommodation charge refunded.
Finally, while you are new to this forum, I have to ask how new are you to overnight Amtrak travel. Since you are looking for same day connections I assume you intend one continuous journey. If so, that is one ambitious itinerary, 6 nights and most of 7 days onboard continuously. If you haven't traveled overnight previously, that is one hell of a start. I have traveled extensively on Amtrak and VIA cross country for years and personally I've found 4 nights, 5 days is about my limit for an unbroken journey. Shortly before COVID, I returned from New York on a continuous NYP-CHI-LAX-SEA journey and I didn't enjoy the last leg on the Starlight all that much. I found myself wishing I had laid over in LA. Part of that was probably having to change trains twice. I find I tolerate 4 nights on the Canadian better, probably partly because the beds are better and partly because it is one through trip. But I am always still glad to get to Toronto, even if I am pushing off early the next morning for a long day's ride on the Maple Leaf.
Honestly, if you have not done multiple night Amtrak journeys before, consider building in a layover. I think you'll find you'll enjoy the trip more, as it might start feeling like a grind.
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