Originally Posted by
yyj9
Sure, if you insure the whole trip. They have sunwing insurance on that part, but I actualy don't know how to insure a trip like this. Pretty sure cc doesn't cover the AE flight (for my son anyway) as I only paid for the surcharges with my cc., and it's not an AE cc. And I think benefits only extend to the card holder and spouse, so he wouldn't be covered anyway.
They spent the weekend in TO on the outbound so I wasn't worried about a misconnect in that direction. And worse case looks like a $90 change fee, or 12,500 miles + taxes plus hotel to get him home, so not really a big deal financially, just a pain logistically which having insurance doesn't really help with.
Is it actually possible to ensure a trip like this that uses miles for part and a charter vacation for another?
Travel insurance generally only works for round-trip flights if I understand it correctly, though presumably if you can speak to an underwriter you can get something more custom-made. Yes, there exists travel insurance for larger trips.
I'm embarking on a trip next month that involves two revenue tix, then an award tix, then a train, then three revenue tix (or 2 rev + 1 award in the case of my traveling partner), and I can get a single-trip plan from Amex that covers that ($90 for my travel partner and me for 6 days though, so it's not all that cheap). It won't cover any loss of points, but it will cover me if, say, I need a hotel for a night due to WX, or if I get delayed/miss a flight on separate tickets provided I've been scheduled to arrive at the airport/my next connection at least 2 hours in advance.