Older travellers with medical conditions are forming smarter financial habits by booking travel insurance early, but millions are still gambling with more than £1,400 by leaving cover until the last minute.
New data from Staysure reveals a stark generational divide in how and when holidaymakers buy protection. While over-50s, particularly those with pre-existing medical conditions (PEMCs), tend to secure cover months in advance, younger travellers are disproportionately waiting until just days before departure and 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% still do.
That means a significant minority of travellers with health conditions are leaving themselves financially exposed right up until take-off. Meanwhile, 18–29-year-olds dominate last-minute purchases, often buying cover as an afterthought rather than at the point of booking.
The result is a growing gap between those who treat insurance as a core part of trip planning and those who treat it as a tick-box task.
Why booking early really matters
Travel insurance does not just cover emergencies overseas. It protects the money spent from the moment a trip is booked. If a holiday is secured in February but insurance is not purchased until the week of an August departure, there is no cancellation protection in the interim. Illness, family emergencies, redundancy or other unexpected events during those months could mean losing the full cost of the trip.
Last year alone, Staysure paid out on 32,063 cancellation claims, totalling more than £45 million. The average claim came to £1,422. At the same time, disruption across UK airports remains significant. According to AirHelp, between January and August 2025 alone more than 22 million passengers experienced disruption, with 3.4 million potentially owed up to £520 in compensation.
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 early insurance becomes critical.
Medical risk and real-world claims
Simon McCulloch, travel insurance expert at Staysure, says there is a clear reason many travellers with medical conditions secure cover well in advance. “Travellers with medical conditions often book earlier because they understand the risks. They know conditions can flare up unexpectedly and that finding the right specialist cover can take time,” he explains. “What many people do not realise is that insurance is not just about what happens abroad. It is about protecting the money you have already spent. If you delay buying cover, you are leaving that investment exposed.”
He also warns that rushing into a last-minute policy without properly declaring medical conditions can invalidate claims altogether, leaving travellers doubly vulnerable.
The financial habit divide
Hannah Mayfield, a money expert working with PayingTooMuch, says the data suggests that older holidaymakers are increasingly approaching insurance as a financial planning decision rather than an afterthought.
“They are booking insurance as soon as they secure their trip, comparing policies carefully and making sure medical conditions are declared from the outset,” she says. “That gives them time to assess value properly rather than panic-buying days before departure and also gives peace of mind that they are covered in case anything happens between booking the trip and actually taking it. ”
By contrast, younger travellers are far more likely to leave it until the last minute. “It can feel like something to deal with later, but that approach carries a financial risk. With data showing the average cancellation claim reaching £1,422, it’s worth asking whether you’re prepared to cover that cost yourself if something goes wrong.”
“So, buying cover as soon as you book your trip gives you the opportunity to check the policy details carefully. It gives you time to shop around and compare travel insurance which can help you find a policy that suits your circumstances and offers comprehensive protection. This also means you’re more likely to secure the right level of cover at the best possible price,” she adds.
The ASAB rule
Experts are urging consumers to follow 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.
With average cancellation claims exceeding £1,400, tens of millions of passengers facing disruption, and a sizeable minority of medically vulnerable travellers 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, the risk sits squarely with you.
