That external travel insurance STILL won't cover gift cards. Read the fine print. Travel insurance for a cancellation usually asks for "proof of payment" and gift cards are generally not accepted. (They want to see a credit card statement, showing WHO paid how much.).
This came up in April, so I want to repeat it for anyone reading this thread:
https://www.disboards.com/threads/trip-insurance-when-paying-with-gift-cards.3943993/#post-65447556
I reached out to the insurance company I used for our covid-cancelled trip to South Africa in 2020, because I was planning to use them for Europe next year. The response I received said, "As long as you can document your purchase of those gift cards through your bank/credit card statements, you would be reimbursed."
So I would just say, check with your insurance provider.
I did get reimbursed for a cancelled cruise. On the Disney giftcard website you can track activity on the giftcards including payment to DCL. My insurance company (Nationwide) accepted it.
It’s all about risk tolerance. I purchased travel insurance for our first couple of cruises but haven’t for the last five. I understand that I may be out the cost of the cruise if I have to cancel after the PIF date, but think I’ll come out ahead in the long run by saving the premiums of the insurance and 10% discounts on fares, excursions, and any extras on board.
I might feel differently once I’m out of pocket one of these days, but I’ve made a conscious decision to take the risk.
I also don’t buy insurance on electronics, concert tickets, or blackjack. Just think you can go insurance poor and companies are making a killing off it. Do have health, auto, home; and life insurance….not that crazy. And my iPhone….too easy to drop that sucker and be out $1000.
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