Any way to protect against losing money?

[hungrycrocodile]

I'm looking to take an expensive trip with my eldest dc towards the end of the holidays (city break with show, trains, accommodation). All in all it's going to be about £500 which is a lot but it's something we want to do and we haven't had a holiday this year.

However (and I know this probably sounds daft) I am paranoid about something going wrong or us not being able to go and losing all that money. I have a toddler with a health issue and we have had to cancel so many plans this year due to her being unwell. We've also all had a lot of illness ourselves. I can pay a little extra for cancellation on the hotel room but I don't think the train tickets or show tickets would be refundable if we had to cancel. It's putting me off booking but I can't leave it much longer or the tickets will go. Is there any way round this?

Travel insurance.

When you buy the tickets there's usually an insurance option. Check it carefully to make sure your worries will be covered. And check the refund policy generally, if the show is popular then the venue often can resell.

Insurance

Remarkably simple innit.

Also buy it on your credit card, you get better protections if the supplier of the services cancels.

Would travel insurance cover show tickets?

Travel insurance typically excludes a claim for a pre-existing condition of a relative.
You can usually buy cover on ticket booking sites but may have same exclusions.
you can buy refundable or movable train tickets but they are not the cheapest.

Possibly , or there may be a resale option to mitigate loss.

Travel insurance typically excludes a claim for a pre-existing condition of a relative.

This^
To get insurance cover you will have to declare all illnesses (usually in last 2 years) anyone taking the trip or a close relative who's illness could affect the trip. Don't just go and buy a bog-standard policy as it won't pay out if you have to cancel due to pre-existing medical conditions.

No need to sneer. If it’s a UK trip of less than 2 nights it may be difficult to get insurance as not classed as a holiday. And/or the required excess may make it unreasonably expensive. Not so simple then.