How can I get out of a trip by buying travel insurance retroactively?

Looks like you can buy insurance up to the day of the trip. However, your cancellation reason will not be legitimate if you knew about it before getting coverage. Getting what you want would require fraud. I would suggest finding a buyer and taking a moderate loss. It's a shitty situation but you are paying for not buying insurance. The rest of us are feeling your pain and will learn from your mistake.

Even if you buy insurance now from sole 3rd party,  i don't think it will be much help as most of the trip insurances covers only in case of medical urgency only. Your best is chance is to check with your ceedit card company if you paid with credit card.

The insurance companies I am familiar with will issue "Cancel for any reason" policies, but only if you get the insurance X days after booking the trip. (Usually two weeks.) I am not a lawyer, but if you buy insurance now with the intention of trying to collect knowing you are going to cancel the trip feels like fraud to me. "For example, it should cover a health reason for which one can easily get a doctor's letter." This feels fraudy to me. Nonetheless, will the tour company refund you the money based on this? If you paid with a credit card, you may be able to get some amount of your payment back, but usually the terms have a time limit starting from when you made the payment. But it wouldn't hurt to give them a call.

Publicize you have tickets for this trip (to family and friends, on social media, on sites like couchsurfing and other travel sites) ... Sell them for a bit cheaper than what they are being sold for on the tour's website. I am sure you'll find someone that would want them. Though I understand some personal reasons might be too compelling, but as someone who likes to encourage people to travel, I'd say that there will always be reasons not to travel. If at all possible, reconsider, move things around, compromise, but do go on the trip. Since you paid for something 2-3 months in advance, it definitely seems like it is a trip you are looking forward to.

Maybe try selling the trip to somebody else since that will be your best bet. I am sure there are rich brats that will be willing to go on that trip if its worth it since it is so expensive. Your personal reasons might help out in the sale when you discuss it with the buyer, that is if you want to.

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