Travel insurance is the policy everyone thinks about at the airport and nobody thinks about at the kitchen table, which is exactly backwards. The mistakes below are the ones I see most often, and every one of them is cheaper to fix before departure than after a claim.
Mistake 1: Assuming OHIP has you covered
Ontario's health plan pays only a very small fraction of out-of-province medical costs, and outside Canada that fraction is tiny compared to actual bills. A single emergency room visit in the United States can run into the tens of thousands of dollars. Travel medical insurance exists precisely because OHIP was never designed to follow you abroad.
Mistake 2: Trusting credit card coverage without reading it
Many premium credit cards include some travel coverage, which is genuinely useful, but it comes with limits: caps on trip length, maximum benefit amounts, and restrictions on who is covered. A card that covers 15-day trips does nothing for your three-week vacation. Read the certificate of insurance, not the marketing brochure.
Mistake 3: Ignoring pre-existing condition clauses
Most travel medical policies require pre-existing conditions to be stable for a set period before departure. "Stable" has a specific definition in the policy wording, usually involving no new symptoms, treatments or medication changes. If your situation changed recently, disclose it and get confirmation in writing that you are covered.
Mistake 4: Buying too late
The best time to buy travel insurance is soon after you book the trip. Trip cancellation and interruption benefits are designed to protect the money you have already committed, and some coverages only apply if you buy within a window after your initial booking. Waiting until the week before departure can leave money on the table.
Mistake 5: Skipping the exclusions
Adventure activities, alcohol-related incidents, and travel against government advisories are common exclusions. If your trip involves scuba diving, backcountry skiing or a motorcycle rental, check whether your policy covers it or whether you need an adventure sports rider. Finding out at claim time is the worst possible moment.
Mistake 6: One policy for everyone without checking the details
Family policies are convenient, but the travellers inside them are not identical. Seniors often face different pricing and medical questions, and children may have different limits. Make sure each traveller's needs are actually addressed rather than assuming the family label covers everything equally.
What to do if you need care abroad
If a medical emergency happens on your trip, call your travel insurer's emergency assistance line as soon as you reasonably can; the number is on your policy documents and often available around the clock. They can direct you to appropriate facilities, coordinate with the hospital, and in serious cases arrange medical evacuation. Keep every receipt and medical report. Travellers who call early almost always have smoother claims than those who wait until they are home to mention a hospital stay.
A note for snowbirds
If you spend months in the US each winter, standard single-trip policies usually will not stretch far enough. Snowbirds generally need dedicated long-stay medical coverage, and the medical questionnaire matters more with age. Start that conversation well before departure season, not in December.
Travelling with medications
If you take prescription medication, pack more than you need in your carry-on, never in checked luggage, and bring a copy of your prescriptions. Some countries restrict certain drugs, so check before you fly. If your medication is expensive or hard to replace, confirm with your travel insurer how emergency prescription replacement is handled. Running out of a critical medication abroad is a preventable crisis.
Before you book, then before you board
- Buy early, ideally soon after booking, to maximize cancellation protection.
- Read the credit card certificate if you are relying on it: trip length caps and benefit limits matter.
- Disclose medical changes and confirm stability requirements in writing.
- Check exclusions for activities, alcohol and travel advisories.
- Never count on OHIP outside Ontario. It was not built for that job.
A good trip is one you remember for the right reasons. Ten minutes with the policy wording before you leave is the cheapest travel companion you will ever have, and it is the difference between a story and a crisis.