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

Suzycoll

simonelkington said:

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!!!

Frankly this seems ridiculous 

So, in essence then you can't book a holiday past the expiry date of your policy?

Is it possible to make the policy a 'rolling' one so it will automatically renew by charging your credit/debit card? 

sheramber

Suzycoll said:

simonelkington said:

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!!!

Frankly this seems ridiculous 

So, in essence then you can't book a holiday past the expiry date of your policy?

Is it possible to make the policy a 'rolling' one so it will automatically renew by charging your credit/debit card? 

Policies can be different from one insurer to the next.
 You need to read the policy document carefully to know what the cover is.
 If in doubt phone the insurer and ask and get for confirmation in writing. 

MyRealNameToo

Suzycoll said:

simonelkington said:

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!!!

Frankly this seems ridiculous 

So, in essence then you can't book a holiday past the expiry date of your policy?

Is it possible to make the policy a 'rolling' one so it will automatically renew by charging your credit/debit card? 

You can, you just won't be insured for it under the annual policy. 

Rolling in travel insurance normally means for the likes of insurance packaged with a bank account which has no start or end date. An annual policy normally offers continuous cover if you renew and you can set policy to auto-renew but the bottom of the barrel providers that dont cover holidays that end beyond the end of this years policy that wouldnt make any difference. 

There is presumably a use case for it, the person who normally doesnt travel but for one year only is taking several trips. For them it would be appropriate and may be cheaper. For others who regularly travel it's not appropriate. Travel insurance is almost exclusively sold on a non-advised basis so its up to you to determine which is the right policy for your needs not the seller (in fact it would be a regulatory breach if they were to advise you if they are only licensed for non-advised sales).