You've booked the flights, paid the deposit, and now the checkout page asks: add travel insurance? Before you click yes, it's worth knowing the downsides that rarely make it into the sales pitch.
The most obvious one: you might never use it. If your trip goes smoothly, the money you spent is gone. And costs aren't trivial - comprehensive policies can run up to 10% of your prepaid, nonrefundable trip expenses. According to Squaremouth figures, the average policy cost $314 in 2026, roughly $21 per day over a 15-day trip. Overseas visitors to the US face particularly steep premiums because of American medical costs.
Timing matters too. If you want perks like pre-existing condition waivers or cancel-for-any-reason coverage, most insurers require you to buy within 10 to 21 days of your first trip payment. Buy late and you lose the option to claim for anything that happened before your policy started - so a storm or emergency that hits before you've signed up won't be reimbursed. Even then, hurricanes that were already named before you bought your policy are typically excluded.
Coverage gaps catch plenty of people out. Many policies exclude pre-existing medical conditions unless you qualify for a waiver, and adventure activities like bungee jumping or backcountry skiing are often left out entirely, meaning you'd need a separate, activity-specific policy. Recent treatment or a change in medication can also complicate things, so it's worth checking the fine print rather than assuming.
Filing a claim is its own hurdle. A 2023 Business Insider survey found only about half of respondents who had filed a claim were satisfied with the outcome. Claims involve paperwork, receipts and documentation, and exclusions can quietly sink a claim even for events beyond your control. If you do buy, keep your policy documents with you, save every receipt, and photograph valuables before packing them.
Finally, you may already be covered without realising it. Homeowners or renters insurance often protects belongings taken on the road - a stolen camera in a hotel room could be claimable at home. Health and auto policies sometimes extend abroad, and credit cards, airlines and booking platforms frequently bundle trip protection as a perk. Reviewing what you already have could save you buying a duplicate policy.
None of this means travel insurance is a bad idea. For expensive, nonrefundable trips, cruises, or travel during hurricane season, it can genuinely earn its keep. The lesson is simply to treat it like any other purchase: check what's already covered elsewhere, read the exclusions, buy early if you want the full range of benefits, and don't pay twice for protection you don't need.
