When to buy travel insurance (and when it’s too late)

You should consider buying travel insurance as soon as you book your trip to ensure you’re covered for cancellations well in advance. Delaying your purchase means you usually won’t be protected for any issues that arise before the policy starts. 

• Best time: the same day (or same week) as you book your trip 

• The latest you can leave it: just before your departure (but earlier is always better) 

• Too late: after you’ve left the UK 

When is the best time to buy travel insurance? 

You should consider buying travel insurance as soon as you book your trip.

Why should I buy travel insurance early? 

You won’t be covered for events that happen before your policy starts, and you’ll miss out on cancellation protection. 

Why is buying late risky? 

You could lose money already spent on flights, hotels, or tours if something goes wrong before your trip. 

Should I buy travel insurance before booking? 

If you’re buying single trip travel insurance it’s best to buy after booking so your policy matches your trip details.

What’s the risk of buying late with a medical condition? 

You won’t have cancellation cover, so if you need to cancel due to illness, you may not be covered. 

Lots of customers delay buying their travel insurance. In fact, over half of Staysure customers buy a policy close to departure, with 54% buying travel insurance in the final 30 days before their trip, and 16% in the final 0-3 days*.  

But if you’ve already spent thousands on flights, accommodation, or tours, not having insurance is a huge gamble. Buying your policy late means you miss out on the following things: 

• Pre‑trip protection and cancellation cover. About a third (33%) of Staysure claims are for cancellation or cutting short a trip. The highest cancellation claim paid in Oct 2024-2025 was £50,412**!  

• Your money is at risk as soon as you book: flights, accommodation, excursions, deposits. 

• Medical conditions: declare any pre-existing medical conditions at purchase so you’re fully covered. But remember, if your health changes later you may need to update your policy details. 

• Less last‑minute stress. 

^{*Staysure sales data, July 2025-January 2026} 

^{**Staysure claims data October 2024 – 2025} 

Travel insurance can cover the cost of a cancelled trip if something unexpected stops you from travelling – as long as the reason is included in your policy and the cover was bought before the event happened.  

Typical reasons you may be able to claim include:  

• You, your travelling companion or a close relative becomes seriously ill or injured  

• You’re made redundant and can no longer afford to travel  

• A bereavement means you need to stay at home  

• You’re called for an emergency work duty  

Single trip cancellation cover starts as soon as you buy your policy while annual multi-trip cancellation cover begins from the day you choose your policy to start.  Travel coverage starts when your trip begins. So, if you’re wondering what your start date should be, you should aim to give yourself maximum coverage before your holiday begins – usually by buying travel insurance the same day that you book your trip. 

For single trip insurance policies your travel insurance ends when you return home (or if you cancel the trip before departure). If you choose an annual multi-trip policy, then it will be valid for 12 months from the start date of your policy. 

Usually the answer is no. Travel insurance prices and coverage are typically based on your confirmed trip details, such as: 

• Travel dates 

• Destination(s) 

• Total trip cost (flights, hotels, tours) 

If you buy it before booking, you may not know those details yet, which can make the policy inaccurate or incomplete. 

The only exception is if you’re planning several trips in a year and you buy an annual multi-trip policy. Otherwise, you should consider getting travel insurance as soon as your bookings are confirmed. 

There are times when you might want to have travel insurance organised before you book your trip, or at least have a quote so you can budget properly. 

• If you already have an annual multi-trip policy, your travel insurance will be arranged before you book your trip. 

• If you’d like to confirm a medical declaration or check your eligibility before spending a lot of money on flights. 

Yes, you can buy travel insurance after booking your flight. You’re only covered for events that happen after the policy becomes active, so consider starting the policy immediately rather than delay the start date.

You can buy travel insurance up to your departure date, but buying last minute means you won’t be covered for anything that’s happened before your policy, and you’ll have missed out on cancellation cover.  

Once you’ve departed the country, it’s usually too late to buy cover with the exception of a few specialist insurers, but you’ll pay a premium and have restricted benefits. 

There’s still time to buy your travel insurance, as long as it’s in place before you leave the country. A last-minute purchase isn’t ideal because if something’s already gone wrong, buying now won’t cover past events.  

 
However, it’s always better to have travel insurance, than not have it at all. So if you’ve just forgotten to arrange cover, then you should still buy it even if it’s the same day that you’re travelling.

Most UK travel insurers won’t allow you to buy a policy after you’ve left the country. This is because once you’ve departed, the risk is “active” – meaning there’s a possibility that you might be buying cover because something has already gone wrong. Because insurers can’t be sure if this is the case, they won’t be able to provide you with a policy. 

You may find that a few specialist insurers offer post-departure travel insurance, but it’s usually: 

• More expensive 

• It has restricted benefits 

• Excludes anything that happened before you bought it 

• It often has a waiting period, meaning your policy won’t begin for 24-48 hours 

• It’s “future-risk cover” and won’t cover medical problems that have already begun, baggage that’s already lost or delays that have already occurred 

There are several scenarios that mean you might need to extend your trip, perhaps because you’re having a great time and want to stay a while longer, or maybe because there are issues with flights and you can’t get home as planned. We look at how these situations can affect your travel insurance below.

If you’d like to extend your holiday and keep the adventures going, the first thing you should do is check your travel insurance to see what the maximum trip duration is. 

If you need longer cover than the policy allows, you’ll need to ensure the extension is arranged before your trip starts.   

If you know you’d like some flexibility around return dates when you’re buying your cover, there’s an optional 100-day extension available on some annual multi-trip policies. 

• A 100-day extension is available on our Comprehensive and Signature policies 

• This optional add-on extends the standard 50-day trip duration to 100 days for one trip 

• It’s only available aged 70 or under 

• You must choose the extension before the start of the trip 

If you’d like to extend your trip, it’s best to get in touch with the Customer Service team as soon as possible (before your departure). 

Each customer’s situation will be unique, so make sure you check your policy details are suitable for your trip before you travel. But generally, as long as you have suitable travel insurance, if your trip is extended due to circumstances outside your control, there’ll be an automatic continuation of cover. This is usually triggered by: 

• Flight delay or cancellation 

• Adverse weather disrupting travel 

• Mechanical issues with transport 

• Strike or industrial action 

• Medical emergencies preventing travel 

All of our Single Trip travel insurance and Annual Multi-trip policies cover you for situations like missed connections or delayed public transport.  

However, our Travel Disruption Extension will give you enhanced coverage. You can add it to our Comprehensive and Signature policies so that unforeseen events, such as cancellations caused by government travel advisories are covered. You can also be covered for additional accommodation and repatriation costs if needed. 

If you have a pre-existing medical condition you’ll likely need to declare it when you purchase your policy (as soon as you’ve booked your trip). But remember to let us know if your health changes before you travel. 

When you declare a pre-existing medical condition, we’ll ask you to complete a medical screening which involves some simple questions relating to the condition(s) that you’re declaring. We’ll then use this information to make sure you have the right cover in place. 

Many of our last-minute buyers still have medical conditions to declare. In fact, 41% of Staysure customers who bought their travel insurance in the final 0-3 days before departure declared a pre-existing medical condition**.  

But, when you leave it to the last few days before departure, you’ll miss out on cancellation cover, so if you have to cancel your trip because you or the person you’re travelling with is unwell, then you won’t be covered. 

^{**Staysure claims data Oct 2024 – 2025.}  

So, now you know the advantages of buying travel insurance as soon as you book your trip (ASAB). Buying it straight away gives you cancellation cover so you’re protected in the weeks or months before you travel.  

But, if you still haven’t got your travel insurance, make sure you buy it before your departure, because most UK travel insurers won’t allow you to buy a policy after you’ve left the country. 

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