Questions about Empire Builder trip, etc.

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My husband and I are planning a trip with the Empire Builder in Septembe, Chicago to Seattle. We need to be in Vancouver by 9/24 to board a cruise on 9/25 heading to Hawaii. The train is a bucket list item for us. We mainly have done east coast trips from DC to NYC and a trip from Seattle to Portland after a cruise.

Here are my questions:
1. We want to stop and spend one or two nights in Whitefish (I chose Whitefish because of the checked luggage, and I am an "overpacker" for cruising). He is not a hiker or can't do long walks due to feet issues. Is one overnight in the area enough to see Glacier NP in the fall via car rental and a few other sights I've gleaned from reading the previous posts?

2. What is the best way to book a trip with a stop in the middle like this? Just book two separate trips? We will be getting a sleeper car for both sections of the trip.

3. Seattle to Vancouver, is it better to book that as part of the last segment of the trip or separately?

Thank you in advance for your sage advice!
 
My husband and I are planning a trip with the Empire Builder in Septembe, Chicago to Seattle. We need to be in Vancouver by 9/24 to board a cruise on 9/25 heading to Hawaii. The train is a bucket list item for us. We mainly have done east coast trips from DC to NYC and a trip from Seattle to Portland after a cruise.

Here are my questions:
1. We want to stop and spend one or two nights in Whitefish (I chose Whitefish because of the checked luggage, and I am an "overpacker" for cruising). He is not a hiker or can't do long walks due to feet issues. Is one overnight in the area enough to see Glacier NP in the fall via car rental and a few other sights I've gleaned from reading the previous posts?

2. What is the best way to book a trip with a stop in the middle like this? Just book two separate trips? We will be getting a sleeper car for both sections of the trip.

3. Seattle to Vancouver, is it better to book that as part of the last segment of the trip or separately?

Thank you in advance for your sage advice!
How about, on your return from the cruise, check baggage to CHI keeping the few things needed?
 
My husband and I are planning a trip with the Empire Builder...

1) Whitefish is certainly the easiest place to rent a car. The stations closer to Glacier only make sense if you have a bus/hotel package lined up.

You can drive the Going-to-the-Sun Road and return to Whitefish in one day (assuming the road is open -- last year an early snowstorm closed it for the season the 3rd week of September.) You won't, however, have time to drive up each of the individual side roads that poke into the park from the east and west, or to cross into Canada and see the Waterton Lakes half of the park. (That may or may not matter to you - Going-to-the-Sun is the most impressive drive and the only one that goes all the way through the park, and gives a fair sampling of what the rest of the park looks like.)

2) I don't think it much matters.

3) Connections from the Empire Builder (or the Coast Starlight) to Vancouver are awkward. Seattle-Vancouver train runs early morning and late evening. You'll have a choice of spending almost a full day in downtown Seattle on foot (or downtown Everett on foot); having a few hours layover and taking a bus; or choosing to spend a night in Seattle and take the morning train to Vancouver the next day.

Booking Whitefish-Vancouver on one ticket will create a guaranteed connection, which may matter if you get very unlucky with a late train.
 
One warning: Make sure you book your trip to the correct Vancouver. (My daughter made the mistake of wanting to go from Seattle to Vancouver, B.C. and instead booked to Vancouver, Washington. Fortunately the mistake was discovered a few days before her trip and it got corrected.)
 
1) That depends on how much of GNP you want to see. The more time you dedicate the more you’ll see. Basically, the more time you have the more ability you’ll have to stop and do/see spur of the moment things (wildlife, glacier activity, etc.)

2) Yes, you’ll have to book two separate trips since you’ll have more than 24 hours between legs.

3) You can do either, but booking it as one trip will automatically create a “guaranteed connection”. If you need to book it as two legs (less than 24 hours in Seattle and using $ for one leg and points for the other) then call and ask for the reservations to be “cross referenced”, this will enable a guaranteed connection in case of an extremely late train.
 
One alternate plan for the very Western end of you train trip would be to spend the night in Everett, WA (EVR) instead of Vancouver, BC (VAC). The early morning train (516) is usually only about 15 to 20 minutes late arriving in Vancouver, so your taxi should get you to Canada Place by about 12:30pm and in plenty of time to join the horde of pax for the three cruise ships there that day.

Did the same after getting off the EB in EVR some years ago and it worked out just fine. But maybe were were lucky.
 
If this is a "bucket list" trip and you're staying overnight in Vancouver, I have lots of nice things to say about the Rosedale on Robson Suite Hotel. A bit pricey, but you do get what you pay for. Best to book directly with the hotel; breakfast is extra if you use Expedia or another third-party site.

If you can extend your trip by another two or three nights, I have even more nice things to say about Victoria on nearby Vancouver Island (reached by frequent ferries from the mainland) and especially the Fairholme Manor, an incomparable B&B within walking distance of the park-like grounds of Government House (we saw deer...).
 
To make sure you connect to cruise, stay overnight in Vancouver. I've been on EB several times they were very late and would miss the boat with same day connection. And of course that is a pain. It only takes a derailment or hitting a car to have you miss same day connection.
 
If you are going to Glacier Park and are not going to be doing much hiking, THE BEST way to see the park is to take a Red Bus Tour. The red buses are 60+ years old and super cool. If the day is nice they will fold the top back and you will be able to look up at the sky and the mountains. The drivers are knowledgeable and fun and the people you meet are usually pretty cool too. The views are amazing.
https://www.glaciernationalparklodges.com/red-bus-tours/west-side-tours/
If you get on at Apgar, get there early so you can have breakfast and take photos of the lake in the early morning, just a beautiful vista!

My husband and I are planning a trip with the Empire Builder in Septembe, Chicago to Seattle. We need to be in Vancouver by 9/24 to board a cruise on 9/25 heading to Hawaii. The train is a bucket list item for us. We mainly have done east coast trips from DC to NYC and a trip from Seattle to Portland after a cruise.

Here are my questions:
1. We want to stop and spend one or two nights in Whitefish (I chose Whitefish because of the checked luggage, and I am an "overpacker" for cruising). He is not a hiker or can't do long walks due to feet issues. Is one overnight in the area enough to see Glacier NP in the fall via car rental and a few other sights I've gleaned from reading the previous posts?
 
Another option if you’re in Glacier for just one day is to stay at the Glacier Park Lodge. It’s a classic NPS lodge and their shuttle service will pick up you and all your luggage at the station and take you to the hotel, a short distance away.

I know they offer tours to several areas on the East side of the park (arguably more scenic than the west side). Not sure if they still offer Going to the Sun trip since Xanterra has taken over operation of other hotels in the park but they may have a connecting shuttle.

It would save you the hassle of car rental and make good use of your limited time. Might be worth a call to the hotel to check out your options (which is often more informative than doing it on line). When we were there Avis had a seasonal car rental office in the general store in East Glacier if you prefer that.
 
It’s a classic NPS lodge [...]

I'm not sure what you mean by "classic NPS lodge" but it is not in the park and not operated under a concession contract with the National Park Service, according to the staff. I do not mean to detract from anything else you said; it is a great place to stay.
 
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