Tommy Lloyd
Author: Tommy Lloyd, Managing Director

Tommy has over 15 years experience within the insurance industry, and his primary focus is helping travellers find the right cover for their medical conditions.

8 min read

There is a wonderful feeling of satisfaction that comes with booking a holiday well in advance. Whether you have secured that specific cabin on a cruise for next summer or found the perfect villa for a family reunion, getting it "in the diary" provides a real boost. It gives you something to look forward to during the greyer months and allows plenty of time to research day trips and restaurants.

However, in the excitement of securing the dates, there is one crucial element that many organised travellers leave on their "to-do later" list: travel insurance.

It is a common thought process. You might think, "I’m not going away for six months, so I don’t need cover yet." But leaving your travel insurance until the week before you travel can be a risky strategy, particularly if you are booking a significant trip far in advance. Here is why getting your cover sorted at the same time as your holiday is one of the smartest travel moves you can make.

Why we love to book early

In recent years, we have seen a definite shift towards booking holidays further in advance. For many of us, especially those enjoying retirement or semi-retirement, the benefits are obvious.

1. The pick of the bunch

If you are planning a cruise, you know that the best cabins - those with the best views or easiest access to the lifts - often sell out a year or more in advance. By booking early, you don't have to compromise on comfort. The same applies to hotels with ground-floor access or specific room configurations that suit your needs.

2. Spreading the cost

Holidays are an investment. Booking early often allows you to secure a trip with a deposit, giving you months to save up the remaining balance. It makes budgeting much easier and can make that dream trip feel more manageable.

3. The joy of anticipation

Planning is half the fun. Having a trip on the horizon gives you months of anticipation. You can take your time reading guidebooks, learning a few phrases of the local language, or simply daydreaming about the sunshine.

What can change between booking and travelling?

While booking six to twelve months in advance has its perks, it also creates a large window of time where life can happen. A lot can change in half a year.

We aren't trying to be pessimistic; we just know that life is rarely predictable. Here are a few things that often crop up for our customers between the day they book and the day they travel:

Scenic View Of Lama Monachile Cala Porto Beach In Polignano A Mare, Italy
  • Changes in health: You might feel fit as a fiddle when you pay your deposit in January. But by July, you could be waiting for a routine operation, or perhaps a niggling back pain has turned into something that requires treatment.
  • Family circumstances: Sometimes, it’s not your health that stops you from travelling, but the health of someone close to you. If a close relative falls seriously ill and you need to stay home to care for them, or if you have a bereavement in the family, you may need to cancel your plans.
  • Provider changes: Occasionally, airlines change their schedules, or accommodation providers face issues that mean they can no longer host you. While package holidays offer some protection here, independent travellers can find themselves in a tricky spot if elements of their trip are cancelled or moved.

If you have to cancel your trip because of these unforeseen life events, you need to know you aren't going to be left out of pocket. 

The financial reality of cancelling

One of the biggest misconceptions we hear is, "I've only paid a £100 deposit, so that's all I'd lose if I cancel."

Unfortunately, that isn't always the case. Most travel contracts have a sliding scale for cancellation fees. As your departure date gets closer, the amount you are liable for increases. Even if you haven't paid the full balance yet, you might still be contractually obliged to pay a percentage of the holiday cost if you cancel.

If you decide to "sort the insurance later," you are effectively self-insuring your deposit and potential cancellation fees for all those months leading up to the trip.

READ MORE: Guide to Cancellation Cover

The View Of The Bay Of Angels In France

Why timing is everything with insurance

This is the most important thing to remember: cancellation cover begins the moment you purchase your policy (or from the policy start date if an annual policy), not the moment you travel.

When you buy travel insurance, you are buying two main types of protection:

  1. Medical and emergency cover for when you are actually on your holiday.
  2. Cancellation cover for the period of time before you go.

If you book a holiday in January for a trip in September, but you don't buy insurance until August, you have missed out on eight months of protection. If you had fallen ill in April and had to cancel, you would have been uninsured, even though you intended to buy a policy later.

By arranging your cover as soon as you book your trip, you lock in that safety net immediately.

A note on annual multi-trip policies

If you are a frequent traveller, you might already have an Annual Multi-Trip policy. This is fantastic, but do check that it is still valid and that it covers the cost of your new booking. If your new holiday is particularly expensive (like a once-in-a-lifetime cruise), you need to make sure your cancellation limit on the policy is high enough to cover the cost of the trip.

READ MORE: Travel Insurance Policy Types

Peace of mind

There is a practical benefit to sorting your insurance early, but there is also an emotional one.

Holidays are about relaxation. They are about taking a break from the admin and stress of daily life. There is a great sense of relief in knowing that the "big stuff" is sorted. You have booked the flights, you have the room you wanted, and you have the policy number saved in your emails.

You can then spend those intervening months doing the fun stuff - shopping for swimwear, planning your reading list, and looking forward to your well-deserved break - safe in the knowledge that if life throws a curveball, you have a safety net in place.

How to get the right cover for your trip

We know that travel insurance can feel like just another piece of "admin" to sort out. But it really is the safety net that allows you to look forward to your holiday with complete peace of mind.

Here is a quick checklist for when you book your next getaway:

  1. Book your holiday: Secure your dates and pay your deposit.
  2. Get a quote immediately: Visit Medical Travel Compared to search for policies.
  3. Be honest about your health: Tell us about any pre-existing conditions so we can find you the right specialist cover.
  4. Check the cancellation limits: Make sure the policy covers the full cost of your holiday (e.g., if your trip costs £3,000pp, don’t buy a policy that only covers cancellation up to £1,000).

Whether you have just clicked "confirm" on a holiday for next year, or you booked a few weeks ago and haven't got around to the insurance yet, it is never too early to get a quote.

We specialise in helping travellers with pre-existing medical conditions finding cover that is right for them. We know that forms can be tiresome, so we have made our online comparison tool as quick and easy as possible. You tell us where you are going and a bit about your health, and we compare prices from over 30 specialist providers to give you a range of options.

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