OK, here's my specifics:
- On US Medicare (No coverage outside the US)
- Have a Blue Cross Medigap plan (they pay everything not covered by Medicare in the US and have coverage in Canada, but only some providers are in their Canadian network, so not sure what would happen if I needed a doctor in a place like Sioux Lookout.
Thus, for the days I'm in the US, I have no problem with medical coverage, but I want to make sure I'm not stuck with a large medical bill while I'm in Canada (a period of about a week.) I'm pretty healthy for my age, but I do have some "pre-existing conditions." actually, I'd be more worried about being hit by a car on the streets of Toronto or Vancouver than getting so sick I can't wait until I return to the US to see a doctor.
-I have a family member who has a medical condition which is pretty stable, but there's always a small chance that I might need to interrupt the trip to deal with a medical emergency.
I made my first reservation (at VIA for the Canadian on April 30. They have a ~C$200 cancellation fee if I cancel before the trip. No refunds after I start the trip. I don't know how VIA handles interrupted trips once you start out.
My Amtrak reservations were made about the same time as the VIA reservations. I figure if I need to cancel on short notice I can either rebook something else down the line or take the 10% penalty and get a refund as an eVoucher, which I will easily use in the coming year. Each leg of the trip (BAL-ALB, ALB-TWO, VAN-SEA, SEA-CHI, and CHI - BAL) is a separate reservation. The only one where a 10% cancellation penalty might really hurt (or at least sting a bit) would be my last leg, the roomette on the Capitol Limited.
My hotels were all booked through the Marriott Bonvoy site and each stay (Albany, Toronto, Vancouver, Seattle, Chicago) is a separate reservation. These can all be cancelled without penalty 2-3 days before arrival. (Marriott seems to be changing from 2 days before arrival to 3 days before arrival penalty-free cancellation.) And I remember when you could cancel without penalty by 6 PM on the day of arrival!) A couple of the nights were booked with "free night" coupons from Bonvoy, which I'm not sure how they handle. So, I would be most concerned about a trip interruption on the Candian on my way to Vancouver or on the Empire Builder on my way to Chicago. For most other trip interruptions, I can cancel the rooms without penalty, barring any family medical emergency.)
For medical coverage I think I'd want something that's secondary coverage after my Blue Cross. For trip interruption, I'm concerned mostly about having to fly home from across the country (or from Canada) on short notice, though I suppose if I have to fly home from Seattle or Chicago, I'd probably be using Southwest Airlines, which tends to have pretty reasonable fares. Also, possible loss of hotel nights (at $200+ per night) and additional hotel costs related to the trip interruption and transfers, etc. could eat up a good bit of money.
For most of the actual travel reservations, I think I can afford to self-insure.
Apparently my Bonvoy credit card (Chase Visa) has some travel insurance, but when I looked it up, it had a lot of exclusions, and I don't think they have any medical coverage. I'm not sure if the Amtrak FNBO car has any similar travel coverage.