Travel Insurance

2026-09-06

When I was younger and without kids I traveled a lot and always thought that travel insurance was kind of a scam. It is like most insurance: car, life, health, etc. use it or lose it. I mostly thing insurance is a scam, insurance companies are incentivized to not pay out so you really got to be careful.

But for some things I really appreciate insurance, like health insurance is a good example. If I or my family get sick I want to go to the hospital and not think too much about costs. I value health a lot and so to me the value of health insurance is high, even if I pay a higher premium than average. And on the other end of the spectrum for me is car insurance, I don’t really need my cars (especially my older crappier ones) with bumper to bumper coverage. I try to see my cars are replaceable, fungible goods. Also I am a cautious driver (mostly) and if I total my car I would rather buy a new one vs pay a high deductible each month. Also dealing with insurance companies is just a pain in the butt, one I am not good at, so I default towards less insurance.

And so back onto the topic of travel insurance, when I was younger (twenties) I never used it and so it seemed like a waste. Every trip I went on I followed through on and there wasn’t a lot of uncertainty in my life. Both hotels and airbnbs offered insurance that I never used, even flights offered it as well but I was never delayed and my plans rarely changed. Perhaps part of this is that I love solo travel or travel with my lovely wife Sneha but not traveling in big groups. I can see how in big groups the schedules become more uncertain and perhaps you have to change plans more frequently.

But I am now in a different phase of life, a different season. I have two young children who get sick or have things pop up, where I will need to delay or cancel travel plans somewhat often. It has been a startling realization but I have done a 180 and almost always book the travel insurance now. Just recently, very sadly, our youngest got sick with a double ear infection and we canceled our trip to Korea, I was looking forward to the trip but was also anxious about the long flight, when we got the diagnosis I thought the best thing to do was cancel. And we were able to get back all of our money relatively easily, there were one or two places where we could not, I think mainly train tickets, but everything else was fully refundable. This was really helpful to us and we were able to conserve money.

So it costs us more upfront to travel now a day, about 5 to 10% more, but so far all of the travel insurance has been worth it. If we cancel one out of ten trips, which is wild to write on the screen but feels true, it will have been worth it. Use it or lose it, and we are in the use it mode for travel insurance.

-Gary