I Skipped Travel Insurance for Years. Then Tokyo Happened.

I bought travel insurance for exactly one trip before I turned thirty, and only because my mother insisted. The policy cost forty-two dollars for two weeks in Japan. On day four, in Tokyo, I woke up with a fever that wouldn't quit, spent an hour in a clinic in Shinjuku, and walked out with a diagnosis of walking pneumonia and a bill for about three hundred dollars. The clinic was excellent. The bill would have hurt. Instead, I emailed the insurer a scan of the receipt and the doctor's note, and the money landed in my account eleven days later. No phone calls, no waiting on hold — a scanned receipt and a short form. My mother has never let me forget it.

What the money actually buys

Insurance doesn't prevent anything, which is why it's so easy to skip. It covers the moment when something goes wrong and the cost is bigger than you can absorb. The three big ones are medical treatment abroad, where a night in a foreign hospital can run into five figures; trip cancellation, which matters when you've paid for flights and hotels months ahead; and lost or delayed baggage, the least dramatic but by far the most common. A decent policy for a two-week trip to Europe or Asia runs about five to seven percent of the trip's cost. Mine was forty-two dollars on a trip that cost roughly a thousand.

When you can probably skip it

Honest answer: short domestic trips, where your own health insurance likely covers you and the flights were cheap enough to eat. If you're driving three hours to visit family and the worst case is a rebooked flight, a policy is often wasted money. But the calculus changes fast with international travel, non-refundable bookings, or anything adventurous. Policies quietly exclude a lot of things, and those exclusions are where people get burned.

Five things worth checking before you buy:

• Does it cover your activities? Hiking a volcano or scuba diving often needs a rider.
• How they define pre-existing conditions — the definitions vary a lot.
• The deductible, and whether the coverage is per trip or for the whole year.
• How you claim — app, email, or a phone number that actually gets answered.
• What counts as a covered reason for cancellation. Cold feet and hangovers don't.

The verdict

Here's my rule now: anything international, I buy it. Anything with climbing, diving, or rented scooters, I buy it. A weekend trip to another state to see my brother — I don't, because I can absorb the worst case. Forty-two dollars bought me a story about my mother being right and a medical bill that didn't ruin a month. And I read the exclusions now, which is the part most people skip. That's a good trade by any measure.