Booking two holidays in different years

Memphisfan

I hope someone can advise.
i am about to book two holidays, one in 2026 and one in 2027, both to the US. I want travel insurance before booking and had wanted single trip due to the price. How can I do this to cover from booking when the second trip is not actually until summer 2027 but the booking date will be Jan 2026?
I hope this makes sense!

bagand96

If you want single trip insurance then you will need to buy 2 policies, one to cover the 2026 trip, and a second for the 2027 trip.

jimjames

You can't buy a single trip policy for 2 different trips. You'll need an annual policies to cover the time or 2 separate trip ones

TELLIT01

I've read that some insurers will do single trip cover up to 2 years in advance.  Unfortunately I don't know who so you will need to do some investigation.  Comparison sites probably won't give that option.

littleredhen

but surely if you are doing 2 trips it's not a single trip??

la531983

Surely its just a poorly worded opening post and he means he wants 2 x single trip insurance policies?

Memphisfan

Thanks for the responses so far. Just to clarify I was originally thinking of a single trip policy for 2026 as an annual policy is very expensive at my age. My main problem is the summer 2027 trip which needs to be covered from booking in Jan 2026. An annual policy would expire before the summer of 2027 trip anyway and if I get a new policy when that expires the trip is covered over two different policies which I’ve heard could be problematic if for some reason I needed to cancel 

Ms_Chocaholic

If buying 2x single trip policies, one for each trip, it might be advisable to do both with the same insurer.

Ms_Chocaholic

Memphisfan said:

Thanks for the responses so far. Just to clarify I was originally thinking of a single trip policy for 2026 as an annual policy is very expensive at my age. My main problem is the summer 2027 trip which needs to be covered from booking in Jan 2026. An annual policy would expire before the summer of 2027 trip anyway and if I get a new policy when that expires the trip is covered over two different policies which I’ve heard could be problematic if for some reason I needed to cancel 

Is there any reason at all that you think that you might have to cancel, illness of family member etc etc  If not I should think you'll be okay

MyRealNameToo

Memphisfan said:

Thanks for the responses so far. Just to clarify I was originally thinking of a single trip policy for 2026 as an annual policy is very expensive at my age. My main problem is the summer 2027 trip which needs to be covered from booking in Jan 2026. An annual policy would expire before the summer of 2027 trip anyway and if I get a new policy when that expires the trip is covered over two different policies which I’ve heard could be problematic if for some reason I needed to cancel 

Im afraid the clarification did give much clarification. 

If you are buying a single trip to cover the 2026 why are you talking about annual policies for the 2027 trip? You'd buy a single trip for each. 

Are you fully committed to the 2027 trip or are you only committed to the extent of a deposit for now? There are providers that go more than 12 months out but your options shrink the further out you go and costs therefore often go up with less competition

heatherw_01

Not sure when your summer date is in 2027, but most insurers allow you to book single trip insurance for up to July 2027 right now, not sure when your travel dates are.
Best to keep checking and book it as soon as it goes on sale for your travel months.

Some insurers MAY let you book even further out, but from my checking, most go up to July 2027 right now.

Bit confused about you mentioning annual policies, but think you mean 2 single trip insurance policies as you said annual was too expensive. Apologies if I misunderstood.