When is the best time to book travel insurance?

When you’re planning a trip, travel insurance is probably somewhere near the bottom of your to-do list, often squeezed in between booking airport parking and remembering to pack a charger. It’s easy to treat it as a tick-box exercise, quickly find the cheapest policy, click buy and move on.

But if something goes wrong, a cancelled flight, lost luggage, a skiing injury, or a medical emergency at sea, then the difference between the right policy and the wrong one suddenly matters a lot more than the price you paid.

Choosing the best travel insurance isn’t about finding the cheapest deal. It’s about finding the cover that actually works for you, your trip, your health, your plans and your risks.

Here’s how to do that properly.

Start with your trip, not the price

Before you even look at policies, take a minute to think about what you actually need to cover.

Think about:

• Where are you going?
• How long are you travelling for?
• What are you planning to do?
• Are you travelling once or multiple times this year?

If you’re heading to Europe for a weekend city break, your needs will look very different from a ski holiday in the Alps or a cruise around the Caribbean.

Winter sports and cruises both come with added risks, and often require extra cover. A standard policy won’t always include them automatically.

If you’re planning on travelling more than once this year, an annual multi-trip policy could work out cheaper, and easier than buying separate cover each time.

Don’t underestimate medical cover

If there’s one part of your policy you shouldn’t cut corners on, it’s your medical cover. This is the part that protects you if you fall ill or get injured abroad and it can quickly become the most expensive part of any claim.

What to look for:

• At least £1–5 million in medical cover (more for destinations like the US)
• Emergency repatriation (getting you back to the UK if needed)
• Cover for treatment on land, on the slopes, or at sea

If you’re skiing or snowboarding, injuries are more common, and mountain rescues can be extremely expensive. Some policies include piste rescue and air ambulance costs, but many don’t unless you add specific winter sports cover.

If you’re going on a cruise, onboard medical facilities are limited. If you need to be transferred to a hospital on land or flown home, then the costs can really start to escalate quickly.

Be honest about your health

This is where a lot of people accidentally invalidate their insurance. If you have any pre-existing medical conditions, even something you consider minor, you need to declare them.

That includes conditions like:

• Asthma
• Diabetes
• Heart conditions
• Mental health conditions
• Ongoing investigations or recent treatments

If you don’t declare something and later need treatment related to it, your insurer could refuse your claim. It might feel frustrating if declaring a condition increases your premium. But not declaring it could cost far more in the long run.

Check what activities, and specialist cover are included

If you’re planning anything beyond lying by a pool, you need to check whether your activities are included.

That could mean:

• Skiing or snowboarding
• Snowmobiling or off-piste skiing
• Scuba diving
• Hiking at altitude
• Water sports
• Adventure activities like zip-lining or quad biking

For winter sports, check specifically for:

• Ski equipment cover (owned or hired)
• Piste closure compensation
• Avalanche delays
• Ski pass cover
• Off-piste rules (often only covered with a guide)

And if you’re going on a cruise, don’t assume a standard policy covers it. You may need cover for:

• Missed port departures
• Cabin confinement due to illness
• Cruise itinerary changes
• Emergency evacuation from the ship

If you assume you’re covered and you’re not, you could end up paying for injuries, disruptions or lost equipment yourself.

Look closely at cancellation cover

Cancellation cover is what protects your money if your trip falls through before you even leave or even during your trip.

This could be due to:

• Illness or injury
• Family emergencies
• Redundancy
• Travel disruption

Make sure your policy covers the full cost of your trip, including all flights, accommodation, excursions, ski passes and cruise packages.

Winter sports holidays and cruises are often expensive upfront, so a low cancellation limit won’t go far if something forces you to cancel.

Also check when your cover starts. Ideally, it should begin as soon as you buy the policy, not just when you travel.

Understand the excess (and the small print)

Every policy has an excess, this is the amount you’ll pay towards a claim. For example, if your excess is £100 and you make a claim for £500, you’ll only receive £400.

A lower premium often comes with a higher excess. That might be fine, but only if you’d actually be able to afford it when the time comes.

Also take a moment to scan the exclusions. This is where insurers list what they won’t cover and it can often be where problems arise.

Common exclusions include:

• Alcohol or drug-related incidents
• Unattended belongings
• Undeclared medical conditions
• Off-piste skiing without proper conditions (like a guide)
• Travel to countries against government advice – check the latest guidance before you travel

It’s not the most exciting reading, but it can save you a lot of frustration later.

Think about your belongings, especially specialist equipment

Baggage cover is useful, but it’s rarely the most important part of your policy, unless you’re travelling with expensive gear.

If you’re going on a ski trip, check whether your policy covers:

• Skis, snowboards, and boots (owned or hired)
• Damage, loss, or theft
• Delays to your equipment

For cruises or longer trips, you might also be carrying more valuables than usual.

Check:

• The total cover limit
• Single item limits (important for phones, laptops, or cameras)
• Whether valuables need to be carried in hand luggage

But remember, replacing equipment is inconvenient. A medical emergency is far more serious, so prioritise your cover accordingly.

Compare policies, not just headline prices

It’s tempting to sort by “lowest price” and click the first option. But that approach can sometimes be misleading.

Instead, compare:

• Cover limits
• What’s included (and what isn’t)
• Excess amounts
• Whether winter sports or cruise cover is included or extra
• Customer reviews and claims reputation

Two policies might look similar on the surface but offer very different levels of protection. The cheapest option is only the better deal if it actually covers what you need.

Buy your policy at the right time

Timing matters more than you might think, it might be tempting to wait until the last minute to buy insurance, but you won’t be covered for cancellation in the meantime.

The best time to buy travel insurance is as soon as you book your trip, especially if you’ve booked a ski holiday or cruise. That way, you’re protected if something forces you to cancel before you travel.

If your flight is delayed, check what you’re owed

Delays are one of the most common travel disruptions, and they’re often where people miss out on money they’re entitled to.

If your flight is delayed, you may be able to claim compensation from the airline depending on the length of the delay and the reason for it. This is separate from travel insurance and can be worth up to hundreds of pounds. Instead of trying to work it out yourself, you can use Resolver’s free flight delay compensation checker to see what you could claim and start the process.

It only takes a few minutes and can save a lot of back-and-forth with the airline.

Know what to do if something goes wrong

Even with the best policy, things don’t always run smoothly, especially when it comes to making a claim.

If something does go wrong:

• Contact your insurer as soon as possible
• Keep receipts and documentation
• Get written confirmation of delays, cancellations, or medical treatment
• Follow the claims process carefully

If your insurer refuses to pay out or you feel you’ve been treated unfairly, you don’t have to accept it. That’s where Resolver can help you raise and manage your complaint.

Choosing travel insurance isn’t about finding a bargain, it’s about protecting yourself properly.

If you’re heading off on a ski trip, taking a cruise, or planning anything beyond a straightforward holiday, a basic policy often won’t be enough.

Take the time to match your cover to your trip, declare your health honestly, and understand exactly what you’re covered for. When something unexpected happens on the slopes, at sea, or anywhere in between, the details of your policy are what determine how well you’re protected.

If you have any thoughts on this topic, or any consumer issues you would like us to cover, feel free to get in touch at support@resolver.co.uk.

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