I have had a similar situation. My friend was going to travel with me (I paid for the trip) but then a medical condition caused her to have to cancel. I decided to continue solo. Very glad I got travel insurance (through USAA).
Windstar required me to pay for the single supplement to continue on the sail solo, and they credited the 65% reimbursable portion of her fare towards the extra cost for my new solo fare. Travel insurance has reimbursed my friend's flight expense, but I'm still waiting to see if they reimburse me for the 35% cancellation penalty that I still have to pay and the single supplement extra cost. My most recent communication with the insurance company seemed promising. Fingers crossed. We had pages of documentation from my friend's surgeon justifying the cancellation. I hope insurance doesn't take the position of, "well, you got the advantage of cabin to yourself so we won't reimburse the single supplement" even though it was technically an "unanticipated" expense caused by friend's cancellation. I was paying for the whole trip either way, though, so I can live with whatever they decide.
On the upside, I just got my travel docs from Windstar today and it appears they upgraded me to a balcony cabin (I had booked an ocean view) that is midship (previously booked cabin was pretty far toward the front). So hey, that's a nice surprise! I think this might be because my original ocean view cabin might be easier to re-sell than the balcony cabin (which has a queen bed that cannot be converted to twins).
I have had a similar situation. My friend was going to travel with me (I paid for the trip) but then a medical condition caused her to have to cancel. I decided to continue solo. Very glad I got travel insurance (through USAA). Windstar required me to pay for the single supplement to continue on the sail solo, and they credited the 65% reimbursable portion of her fare towards the extra cost for my new solo fare. Travel insurance has reimbursed my friend's flight expense, but I'm still waiting to see if they reimburse me for the 35% cancellation penalty that I still have to pay and the single supplement extra cost. My most recent communication with the insurance company seemed promising. Fingers crossed. We had pages of documentation from my friend's surgeon justifying the cancellation. I hope insurance doesn't take the position of, "well, you got the advantage of cabin to yourself so we won't reimburse the single supplement" even though it was technically an "unanticipated" expense caused by friend's cancellation. I was paying for the whole trip either way, though, so I can live with whatever they decide. On the upside, I just got my travel docs from Windstar today and it appears they upgraded me to a balcony cabin (I had booked an ocean view) that is midship (previously booked cabin was pretty far toward the front). So hey, that's a nice surprise! I think this might be because my original ocean view cabin might be easier to re-sell than the balcony cabin (which has a queen bed that cannot be converted to twins).
