Annual multi-trip cover not covering trips spanning two ‘annual’ periods

simonelkington

Hi all. 

I’ve just had a conversation with my travel insurer (StaySure) and am totally baffled by their response to my question that I feel I need your thoughts on this - surely the insurance industry doesn’t all operate like this??

I have a currently Annual Multi-Trip policy with StaySure that expires at the end of November 2025.

I have just booked a holiday for January 2026.

Following Martin Lewis’ advice with regards ensuring you have travel insurance from the time of booking, I just called StaySure to create a new policy starting the day after my current policy ends (i.e. end of November 2025 to end of November 2026) thinking that would have me covered for the January 2026 trip.

However, after 30 mins on the phone, I was told the following…

Regarding my current policy ending in November 2025, if I were to have to cancel my January 2026 trip tomorrow I wouldn’t be covered. I get this - that makes total sense as the policy ends before the trip is due to take place.

However, they also told me that if I bought a new annual multi-trip policy today starting from the day after the current one expires (end of Nov 2025), I also wouldn’t be covered for the January 2026 holiday if I had to cancel it tomorrow (because the policy doesn’t become live until the start date).

I also can’t have multiple, overlapping policies! So from what they’ve told me, there’s no way to ensure my January 2026 holiday is covered from today, without just having a single trip policy for it - surely that can’t be right…..?

For context, my partner has pre-existing health conditions so we don’t have the privilege of shopping around much with other companies.

Thanks all for your help!!!

mebu60

Was an option discussed to take out a new annual policy from now and cancel the existing one with a pro-rata refund credited to you? Or cancel the existing one with no refund if that's what the Ts&Cs say and take out a new annual policy from today? 

simonelkington

mebu60 said:

Was an option discussed to take out a new annual policy from now and cancel the existing one with a pro-rata refund credited to you? Or cancel the existing one with no refund if that's what the Ts&Cs say and take out a new annual policy from today? 

Thanks for the response - they said I wouldn’t get a refund on the existing one as it’s after the 14 day cooling off period. At the moment, it looks like that’s the only option - to cancel the existing, not get a refund and then re-book, but it seems ridiculous this is the only way to do it.

simonelkington

Update: I’ve now spoken with someone else at StaySure who has told me that I would be covered for the January 2026 trip under my current policy if I were to (for example) get a serious illness before the end of the current policy - even though the trip itself is not in the time period of the existing policy. If there are any insurance gurus out there who could confirm that, I would be very grateful!!!

Brie

take out a single trip policy?

MyRealNameToo

simonelkington said:

Update: I’ve now spoken with someone else at StaySure who has told me that I would be covered for the January 2026 trip under my current policy if I were to (for example) get a serious illness before the end of the current policy - even though the trip itself is not in the time period of the existing policy. If there are any insurance gurus out there who could confirm that, I would be very grateful!!!

It varies by insurer, many operate on a continuous cover basis so will cover and others dont. You can see an example in a declined FOS complaint https://www.financial-ombudsman.org.uk/decision/DRN-5199115.pdf

The policy book clearly stated that it only covered trips that started and ended within the period of the insurance and they failed to declare the medical condition on renewal. 

TELLIT01

simonelkington said:

Update: I’ve now spoken with someone else at StaySure who has told me that I would be covered for the January 2026 trip under my current policy if I were to (for example) get a serious illness before the end of the current policy - even though the trip itself is not in the time period of the existing policy. 

That is certainly how any annual insurance policy I've ever taken out works.  Anything which happens during the life of the current policy which causes a holiday to be cancelled, even if the holiday is after the policy expires, is covered.

That said, I only used StaySure once due to the small print, which I admit I hadn't read until I saw a complaint about their claim handling.  Thankfully I wasn't affected by the issue raised, but it did make me compare policies thereafter.

simonelkington

Thanks everyone. I’ll go through the small print with a fine tooth comb to double check!!

MyRealNameToo

simonelkington said:

Thanks everyone. I’ll go through the small print with a fine tooth comb to double check!!

Many forms of consumer insurance is actually a fairly complex product so the fact that so many people buy on price alone, often encouraged by the likes of this site and more so by its parent company (money supermarket). It's no surprise how many posts we get of people complaining that their claim has been declined but when you spend 2 minutes reading the policy book it's clearly excluded. 

lisyloo

simonelkington said:

Update: I’ve now spoken with someone else at StaySure who has told me that I would be covered for the January 2026 trip under my current policy if I were to (for example) get a serious illness before the end of the current policy - even though the trip itself is not in the time period of the existing policy. If there are any insurance gurus out there who could confirm that, I would be very grateful!!!

I normally keep a couple of that e.g. if it’s in chat I get a transcript and take screenshots on my phone.
if it’s verbal then ask for it to be confirmed in email.