The easy answer would be “always.”

That’s because trip cancellation is designed to be there for when you least expect to use it. Here is what we mean: any time you purchase travel insurance for a trip you don’t expect to really happen, by the very nature of travel insurance — and any insurance product, for that matter — your policy isn’t likely to meet a covered reason for trip cancellation. (And if it did, the insurance industry would likely go belly up before you knew it.)

Here is an example: You book a weekend getaway at an island retreat smack dab in the middle of a named hurricane’s path, and you purchase a travel insurance policy with a trip cancellation benefit. With those facts alone, your cancellation was already expected or reasonably foreseeable. And you won’t be covered for trip cancellation protection.

You also need to make an honest effort to make the trip happen and not simply let it pass you by. Let’s pretend that instead of a hurricane, your trip just faces some nasty weather. And instead of packing up, you pack it in, staying home and assuming you’ll be covered for trip cancellation. Once again, you’d be wrong.

So if you already know a trip likely won’t happen, or you’re not going to try to make it happen, trip cancellation protection is likely a non-starter.¹

That said, there are many times when seeking out a policy with trip cancellation protection makes a ton of sense.

Let’s take a closer look at a few…

When You Have Pre-Paid, Non-Refundable Expenses

Have you made pre-paid, nonrefundable purchases, ranging from hotel stays to airfare and concert tickets, for your trip? If so, trip cancellation can provide you reimbursement, depending on the specifics of your policy and provider. That’s really the benefit behind trip cancellation protection, providing you a means of protecting this investment. The peace of mind helps, too. The more you spend on these pre-paid, non-refundable expenses, the more you might consider getting a policy with trip cancellation protection just so you don’t stay awake imagining scenarios in which your trip is cancelled, from your basement flooding to surprise emergency back surgery. Just know that plans have limits, so check your policy carefully, and you’ll want to keep all the documentation associated with these purchases to make a claim.

Also, know that you’ll need to meet a covered reason for trip cancellation protection. We’ve already dropped the term “covered reason” a few times in this article. These are situations, circumstances, and events that may provide you eligibility to make a claim, and can range from losing your employment to getting called for jury duty and specific medical conditions that may arise. In fact, there can be dozens of covered reasons for trip cancellation, depending on your plan and provider, so you’ll want to become familiar with them.

When You’re Travelling at the Last Minute

For one simple reason: the closer you are to your trip date, the more likely the window for cancelling or changing that hotel or rental car reservations has passed. And you remember what trip cancellation protection helps with, right? If you said prepaid, nonrefundable purchases, you get a prize!

When It’s Flu Season

If you’re healthy when you book your trip and purchase a travel insurance plan, then it’s perfectly reasonable to think you’ll be healthy when it comes time to travel. That’s true even during Flu season, which takes place around October through May of each year.

But life happens. And so does the Flu, even if you’ve taken preventive measures. Depending on your travel insurance plan and provider, you may be eligible for trip cancellation if you (or one of your travel companions) contract the Flu and your doctor advises you against traveling. Just be sure to get a note. We’ve actually written an entire article about traveling with the Flu (or not traveling), and we encourage you to check it out.²

Note that while certain medical conditions and emergencies may be grounds for trip cancellation, you’ll want to take a close look at your letter of confirmation to see what can be covered and what cannot, especially if you have a pre-existing condition. In that case, you’ll need to be medically cleared to travel on the day you purchase your travel insurance policy and meet some other conditions laid out here. 

When You’re Flying

Road trips, by their very nature, often come with more flexibility than flying. Sure, you may have to battle bumper-to-bumper traffic. But you don’t need to arrive at your car four hours early, stand at a TSA checkpoint, and be subject to delays, cancellations and other unexpected inconveniences that are often outside your control. These are all reasons why you should consider a travel insurance plan with trip cancellation protection if you’re flying — especially if it’s a pre-paid, nonrefundable ticket. Actually, even if you’re flying for free or on the cheap thanks to loyalty points, there may be fee for shuffling those back to your account if a flight is cancelled. Don’t worry, there is a travel insurance benefit for that, too, the Frequent Traveler Reward Program.

The Final Word on Trip Cancellation

Maybe you're heading on a two-week African safari. Or you're swooping into Seattle for a big business meeting and taking the red-eye back to the East Coast. In either case, trip cancellation protection can come up big when it comes to safeguarding your investment and providing you peace of mind. And while we work to make the process for filing a trip cancellation clam simple, do know that there are a few steps to walk through (You can find them in this checklist.) But before you get there, you’ll need to make every possible effort to reach your destination. In fact, to qualify for cancellation protection, you’ll have needed to miss more than 50 percent of your scheduled trip due to a covered reason. Even if the odds seem stacked against your trip, don’t give up!³

This is the same way we started out this article. So maybe it’s also the best answer for that question about when to purchase travel insurance with a trip cancellation benefit: for any trip you actually plan on taking.

Related Articles

• 5 Reasons Your Trip Cancellation Insurance Won't Cover You
• Trip Cancellation Insurance: Covered Reasons Explained
• Trip Cancellation During Cold and Flu Season