Travel insurance: what to look for and what actually matters

At dinner recently, someone mentioned they were heading to Southeast Asia for a month and had booked everything except travel insurance because “they’ll get around to it”. Six people at the table nodded. I nearly knocked over my wine.

I didn’t say anything super dramatic, but I mentioned that two years ago I had to coordinate getting my mother home from the Caribbean on a medical flight after she became gravely ill. She was hospitalised for two weeks before she was stable enough to be transported. The medical flight home was its own ordeal. And she had the “good travel insurance”, the one that my sister insisted she purchase when booking her trip. The process of using the travel insurance – the calls, the paperwork, the back-and-forth with adjusters while managing a real medical emergency from another country – was something I would not wish on anyone.

The table got quiet. Then someone said, “right, what company do you recommend?”

Which is the wrong first question. But we’ll get there.

Travel insurance is not a product you buy on a whim and forget. It’s a contract, and the terms can vary considerably between plans. The difference between a plan that actually covers you and one that mostly covers you is not always obvious from the summary page. Here’s what you need to look at, and what actually matters when things go wrong.

Trip cancellation coverage

This is the most visible part of any travel insurance policy, and the part most people think about when they imagine needing it.

Trip cancellation typically reimburses your prepaid, non-refundable costs (flights, hotels, tours, cruise deposits) if you have to cancel before you leave. Standard plans only pay out if your cancellation falls within a defined list: unexpected illness or injury, death of a family member, severe weather (think hurricane), jury duty, military deployment, that sort of thing. Changing your mind, found a better deal, relationship break-up? Not covered.

The reason list matters more than most people realize, because plans can differ significantly. Some include job loss. Some include natural disasters at the destination. Some require a doctor’s letter to support a medical cancellation claim. Read that list before you buy.

One practical thing worth doing before you buy anything: run the numbers. Weigh the cost of the insurance against the total non-refundable cost of the trip. If your non-refundable exposure is minimal, a basic plan may be sufficient. If you have $20,000 sunk into flights, hotels, and a cruise deposit, you’re probably going to want something more comprehensive. The insurance should be proportional to what you stand to lose should the unexpected happen.

Pre-existing conditions

If you have a pre-existing medical condition, standard plans will typically exclude any cancellation or medical claim related to that condition, unless you purchase a pre-existing condition waiver. The catch is that waivers come with strict timing requirements. Most require you to purchase the policy within 14 to 21 days of your first trip deposit. Buy it a few weeks later and you lose the waiver. This is one of the most common and costly mistakes travellers make, and it’s almost always avoidable.

To qualify for a waiver, you also need to be medically stable at the time of purchase (no recent changes to medications or treatment) and insure the full non-refundable cost of the trip. It’s all or nothing; you either meet every condition or you don’t have it.

If you’re over 50 and travelling with any ongoing health condition, this is not optional reading. Buy your policy as soon as you make your first booking deposit.

Cancel for Any Reason (CFAR)

Standard cancellation coverage won’t help you if you want to cancel for a reason not on the covered list – general anxiety, a change in circumstances, or simply because you’ve changed your mind. Cancel for Any Reason (CFAR) upgrades exist for exactly that situation. They let you cancel for any reason at all, and get back roughly 75% of your prepaid non-refundable costs. CFAR typically cost at least 50% more than a standard policy and must be purchased close to your initial deposit. It’s not for everyone, but if your trip involves significant non-refundable costs and any uncertainty, it’s worth knowing it exists.

Medical coverage abroad

Most domestic health plans, including provincial coverage in Canada, do not cover you outside the country. Some provide minimal reimbursement for genuine emergencies, but the gap between what they will pay and what a private hospital abroad charges can be enormous. Do not assume your home coverage travels with you. Check specifically, because the answer is almost always “not the way you’d hope.”

For travel medical coverage, $200,000 should be considered a bare minimum. Hospital stays, specialist fees, diagnostic imaging, medications, and emergency procedures, especially in countries without a public health system, add up very quickly. Private hospitals in tourist destinations are not known for modest billing.

Emergency evacuation coverage

This is the line item most people underestimate, and it’s also potentially the most expensive thing that can happen to you abroad.

Medical evacuation covers the cost of transporting you to the nearest adequate medical facility, or if local facilities cannot properly treat you, getting you home. An air ambulance (a specially equipped aircraft with medical staff on board) can cost anywhere from $50,000 to over $250,000, depending on where you are, how far you need to travel, and what type of medical staff is required.

My mother’s situation involved a medical flight home with a nurse and an ER doctor. The transport cost alone was significant. Her policy covered it. But being on the inside of that process made very clear why $50,000 in evacuation coverage is not really coverage; it’s a partial contribution toward a very large bill.

My recommendation? Look for a minimum of $250,000 in medical evacuation coverage. Some solid comprehensive plans offer $500,000 or more. This is not a line item to economiz

e on.

Primary vs. secondary medical coverage

This distinction is buried in most policy summaries. Secondary coverage means the travel insurer pays after your regular health insurance. In practice, you submit your claim to your home insurer first, wait for them to process it (and likely decline most of it, since you’re abroad), collect a formal denial letter, then submit everything to the travel insurer. This takes weeks, possibly months. If you’re recovering from a serious illness or injury, that is not a process you want to be dealing with.

Primary coverage means you go directly to the travel insurer to make a claim. No submitting to your home plan first, no collecting denial letters, no waiting on a third party before your claim will even be looked at.

Here’s what often doesn’t get mentioned: even with primary coverage, filing a travel insurance claim for a serious medical situation is a real undertaking. When my mother was hospitalised, the insurer required itemized invoices for every charge. Private hospitals itemize everything; every syringe used, every medication administered (even if it’s only Tylenol), every procedure performed (even the taking of vitals which happens several times a day), day by day. Getting those documents organized while simultaneously managing a medical emergency from another country is a lot. Primary coverage at least means you’re doing it once, with one company. Secondary means doing some version of it twice.

Pay the extra for primary medical coverage. In most cases, the premium difference is not as large as people expect. The difference in experience, if you ever need to file a claim, is significant.

What your credit card might already cover

Before buying a standalone policy, check what your credit card might provide. Many travel rewards cards include trip cancellation, interruption, and emergency medical coverage as a cardholder benefit. The coverage limits, conditions, and age restrictions vary considerably between cards, so it is worth reading the actual benefits guide, not just the marketing page.

I have a Gold American Express, and it includes solid travel insurance coverage. I’ve been fortunate in never having needed to use it. But as I get older, I intend to re-evaluate, because age is where credit card travel insurance often becomes insufficient without anyone flagging it.

Most Canadian credit cards significantly reduce emergency medical coverage once you turn 65, often dropping from 21-60 days of coverage, down to 3–15 days. If you’re planning a longer trip and assuming your card has you covered, check the age conditions first.

The Canadian cards most consistently cited for strong travel insurance coverage:

The National Bank World Elite Mastercard is widely considered the strongest overall option in Canada. Emergency medical coverage goes up to $5,000,000 CAD, with 60 days of coverage for travellers under 55, and 15 days for those 65 and older. That’s still above average for the category.

The Scotiabank Passport Visa Infinite offers solid comprehensive coverage, no foreign transaction fees, and a delayed baggage benefit of $1,000 if your checked bag is delayed four or more hours.

The Scotiabank Platinum American Express is particularly worth knowing about if you’re in the 70+ years bracket. It’s one of the only Canadian credit cards that offers emergency medical coverage for cardholders aged 75 and older (10 days). That is genuinely rare and worth paying attention to.

That said, credit card coverage is a supplement, not a substitute. Most cards won’t match the evacuation limits, primary medical coverage, or pre-existing condition waivers available through a dedicated travel insurance policy. The card is a useful starting layer. Whether it’s sufficient depends entirely on the trip you’re taking and the coverage you actually need.

If you ever need to make a claim, documentation is everything.

I hope you never experience a medical emergency abroad; it is probably the most stressful thing I have ever endured. However, should you find yourself in a situation, here is my best advice.

Keep every invoice, bill, and receipt, and take pictures of them with your phone. If the hospital or clinic can’t provide one immediately, follow-up in writing and document that you asked. Write down every conversation: the date, the time, who you spoke to, what they said, who else was present, and what the outcome or next steps were. That applies to doctors, hospital administrators, and insurance adjusters/representatives equally. Do the same for every email, and make sure to copy yourself.

Insurance companies process claims based on paperwork. If you can’t prove it happened, or what it cost, the claim becomes a negotiation rather than a straightforward reimbursement, or might be deny all together. The better your records, the less room there is for delays or disputes.

It’s not glamorous advice. But it’s the advice I wish someone had told me before I needed it.

The right first question

The question at that dinner table “what company do you recommend?” is the wrong place to start. The right first question is: what do I actually need?

Work out your total non-refundable trip costs (that’s your cancellation exposure), your destination’s healthcare situation (medical limits), how remote you’ll be (evacuation coverage), your age and any health conditions (pre-existing condition waiver, coverage duration), and what your credit card already provides so you’re not paying twice for the same thing.

Then shop. The cheapest option and the right option are rarely the same thing in travel insurance, and the gap between them tends to reveal itself at the worst possible time.

Buy it early. Read the fine print. And please, do not leave it until the week before you fly.

Do you have a travel insurance provider you love, or a question I didn’t cover? Leave a comment below – I read every one!

Now that the trip is protected, you might as well make sure it runs smoothly too. My post on Smart Travel Tech For A Smoother Take-Off covers the gadgets and tools that actually earn their place in your bag.

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