collaborative post | Older travellers with medical conditions are forming smarter financial habits by buying their travel insurance early, but millions of Brits are still gambling with more than £1,400* by leaving cover until the last minute.
New data* from travel insurance provider Staysure reveals a stark generational divide in how and when holidaymakers buy their protection. While over-50s, particularly those with pre-existing medical conditions (PEMCs), tend to secure their cover months in advance, younger travellers are disproportionately waiting until just days before departure – that delay could prove costly.
A clear split in behaviour
Among travellers purchasing insurance 89 days or more before departure, 72% have pre-existing medical conditions, and over-50s account for 92% of those early bookings. By contrast, of those buying cover just 0-3 days before travelling, 59% have no medical conditions, but 41% of them do.
That means a sizeable number of travellers aged over 50 with health conditions are leaving themselves financially exposed without cancellation cover right up until their departure day. Meanwhile, 18–29-year-olds dominate last-minute purchases, often buying their cover as an afterthought rather than at the point of booking their holiday denying them enough time to research the cover they need.
The result is a growing gap between those who treat travel insurance as a core part of trip planning and those who leave it last minute without truly understanding its value and the benefits of having cancellation cover in place.
Medical risk and real-world claims
Dr Asimah Hanif, a registered NHS GP working with Staysure, says travellers with pre-existing medical conditions often approach travel insurance earlier because their health needs require more careful planning.
“People living with medical conditions are usually more aware that cancellation cover is a core part of travel insurance protection as unexpected health changes can happen without warning,” she explains. “That’s why many choose to arrange their travel insurance well in advance, making sure their condition is properly declared and that the policy covers their specific medical needs should they need to cancel or require treatment abroad.”
“From a medical perspective, even conditions that are stable day-to-day can sometimes flare up or require unexpected treatment potentially disrupting holiday plans before departure or while abroad particularly when dealing with different climates, or changes to routine,” she adds.
“However, she says a surprising number of travellers still delay arranging cover until the last minute. But leaving it too late can mean rushing through medical screening questions or not fully understanding what your policy does and doesn’t cover.”
“Buying appropriate medical travel insurance as soon as you book your holiday gives you time to go through the medical declaration process carefully and make sure your condition is accurately recorded,” she adds. “That way you know you’re properly protected if something changes with your health before you travel forcing you to cancel or if you need medical treatment while you’re away.”
The ASAB rule
Travel insurance is not only there to cover medical emergencies overseas. It also provides important financial protection for the cost of your holiday and experts are continuing to urge travellers to follow the one simple principle: ASAB (As Soon as Booked).
The rule applies to everyone, not just those with medical conditions. From the moment a holiday deposit is paid, money is at risk if you don’t have the appropriate insurance.
For example, if you book an August holiday in February but delay buying travel insurance, you risk losing the money spent on the holiday as you don’t have cancellation protection in place during those months. If something unexpected happens such as illness, injury, a family emergency, redundancy, or another event outside your control and you’re unable to go on the holiday you could lose the full cost of your trip.
This could also be the case if you’ve only paid a deposit as you may still legally be required to pay the remaining balance, even if you can’t travel.
In 2025, Staysure customers alone made 32,063 claims* for the unexpected cancellation of their holidays which accounted for almost 42% of claims – a sum totalling more than £45 million. The average cancellation claim came to £1,422 per person. With so many people heading abroad this year, it could mean millions are left out of pocket if they are forced to cancel without cover.
Furthermore, between January and August 2025, more than 22 million passengers flying from UK airports experienced disruption, with more than 1.1 million potentially eligible for compensation, according to AirHelp.
While airline compensation may cover certain delays or cancellations, it does not automatically reimburse prepaid hotels, excursions or other non-refundable elements if the wider trip collapses. That broader financial protection is where travel insurance becomes critical under the cancellation benefit.
A true divide in buying behaviour
From a consumer habit perspective, experts say the issue isn’t only about when travellers buy insurance, it’s about how they research it.
Many holidaymakers still treat travel insurance as a box-ticking exercise, often buying the cheapest policy or leaving the decision until the final days before departure. According to comparison specialists, that lack of preparation can result in travellers missing important policy details or selecting cover that doesn’t match their holiday plans.
Hannah Mayfield, a money expert working with PayingTooMuch, says that researching and comparing policies aligned to the ASAB rule is just as important as purchasing early.
“A lot of people assume all travel insurance policies are essentially the same, but the reality is that their benefits and level of cover can vary significantly between policies and providers. For example, consider how much you’ve spent on your holiday and look for cancellation cover that will cover that cost.
Buying your insurance early means you have enough time to research those who provide cover for medical conditions and compare policy benefits properly to suit your needs. This includes cancellation and baggage limits, cover for medical emergencies, excesses, and any trip-specific cover you might need such as activities, winter sports, cruise or other add-ons.
When you leave it until the last minute, it can be tempting to rush the decision or default to the cheapest option, which isn’t always the best. Budget policies may come with higher excesses or limited cover, so it’s essential to ensure that the policy you choose offers the right level of protection.
Treating travel insurance as part of your core holiday planning, rather than an afterthought, helps ensure you compare policies that genuinely fit your trip and your needs protecting you from the moment you buy.”
With unexpected cancellations potentially costing travellers thousands of pounds and many still buying cover at the eleventh hour, the financial exposure is real.
The message from industry and money experts is consistent: once the trip is booked, the clock starts ticking and if insurance is not in place, you risk losing that money.
*Staysure sales data looking at a six-month period from 15th August 2025 to 15th January 2026
*Staysure internal claims data (TiCorp, January 2026). Based on 32,063 cancellation claims paid in 2025, totalling £45,618,127.70. Average claim value £1,422.77.