Travel Insurance Explained

Everything I Wish I Knew Before That Trip to Thailand

Let me tell you about the time I broke my ankle in Chiang Mai. Long story short: I did not have travel insurance. The hospital bill was… let us just say my wife still brings it up whenever I suggest skipping coverage to save a few bucks.

So yeah, I am a travel insurance convert now. And I have done way too much research on this topic, which means you do not have to. Here is what actually matters.

The Main Types of Coverage (And Which Ones You Actually Need)

Trip Cancellation Insurance

This one is pretty straightforward. If you can not go on your trip for a covered reason, you get your money back. Covered reasons usually include getting sick, family emergencies, jury duty (had a friend deal with that one), or natural disasters hitting your destination.

My opinion? Only worth it if your trip costs a lot AND is non-refundable. That $200 flight to Vegas with flexible tickets? Probably skip it. That $8,000 guided tour of Patagonia? Yeah, insure that.

Medical Insurance for Travel

This is the one that would have saved me after the Thailand incident. Kidding – I did not have it then, remember? But I ALWAYS get it now.

Here is what most people do not realize: your regular health insurance might not work abroad. I have talked to so many people who assumed their Blue Cross or whatever would cover them internationally. Sometimes yes, often no. And even when it does, the coverage might be garbage.

Travel medical insurance covers hospital stays, doctor visits, and sometimes medical evacuations. Speaking of which…

Medical Evacuation Coverage

This is the one that sounds dramatic until you need it. If you get seriously hurt somewhere remote, someone needs to get you to a real hospital. Helicopters, medical flights, whatever it takes. This stuff costs a fortune – we are talking $50,000+ for some evacuations.

I personally always include this if I am going anywhere with questionable healthcare infrastructure. Not because I am planning to get hurt, but because you never plan to get hurt.

Baggage Coverage

Airlines lose bags. It happens. This coverage gives you money to buy essentials if your stuff disappears or shows up three days late. Usually also covers theft or damage.

Honestly? I rarely worry about this one. Credit cards often include some baggage protection, and airlines are required to compensate you for lost luggage anyway. But if you are traveling with expensive gear – camera equipment, sports stuff, whatever – it might be worth adding.

Trip Interruption Insurance

Different from cancellation. This kicks in if you are already on your trip and have to cut it short. Maybe there is a death in the family, maybe you get super sick. It covers the unused portion of your trip plus getting you home.

How to Actually Pick a Policy

Here is my completely biased process:

First, figure out what you are worried about. Beach vacation in Mexico? I am mostly thinking about medical stuff. Adventure trip with lots of activities? Medical plus maybe some coverage for the activities themselves. Expensive multi-leg international trip? Probably want cancellation coverage too.

Then, check what you already have. Your credit card might include some travel protections. Your health insurance might work internationally. Some homeowner policies cover theft of belongings. Do not pay twice for the same thing.

Read the exclusions. I know, nobody wants to read the fine print. But this is where they tell you all the ways they will not pay you. Pre-existing conditions, dangerous activities (sometimes they define this differently than you would expect), and specific scenarios that are not covered. You need to know this stuff.

Compare at least three options. Prices and coverage vary wildly. I usually check sites like Squaremouth or InsureMyTrip where you can compare policies side by side. Saves a lot of time.

The Mistakes I Have Made (Learn From Them)

Waiting too long to buy. Some benefits – especially the cancel for any reason upgrades – only work if you buy within a certain window of booking your trip. Usually 14-21 days. Miss that window and you are out of luck.

Not disclosing health stuff. Look, I get it, nobody wants to admit they have health issues. But if you do not disclose pre-existing conditions and then need to claim something related to them? Denied. Be honest on the application.

Assuming adventure activities are covered. I went white water rafting on a trip once, assuming my travel insurance had my back. Turns out it specifically excluded whitewater activities above Class II rapids. We did Class IV. Would have been a problem if anything happened.

Not keeping documentation. If something goes wrong, you need proof. Receipts, police reports for theft, medical records, photos of damaged items. Keep everything. I now take photos of all my packed items before I leave – sounds paranoid, but try proving what was in your lost bag otherwise.

Is It Actually Worth the Money?

Okay, real talk. Most trips, nothing goes wrong. You pay for insurance you do not use. That is literally how insurance works. You are paying for peace of mind and protection against the unlikely.

But when things do go wrong? They can go REALLY wrong, really expensively. That ankle I broke in Thailand? Without insurance, I was looking at about $4,500 in medical bills. Could have been worse – that was just a fracture. Imagine if I had needed surgery or an ICU stay.

My personal rule: If the trip costs less than $1,000 total and I am going somewhere with accessible, affordable healthcare? I might skip it. If the trip is expensive, remote, involves adventurous activities, or I am going somewhere with expensive medical care? I always get coverage.

Your risk tolerance might be different, and that is fine. Just make the decision intentionally, not just by forgetting to think about it.

One Last Thing

Buy it as soon as you book your trip. Not the week before you leave. Not at the airport. As soon as you book. That gives you maximum protection for the maximum amount of time, and it makes you eligible for all those time-sensitive benefits.

Alright, that is my travel insurance brain dump. Hopefully you never need to use yours, but if you do, you will be glad you have it. Trust me on that one.

Richard Hayes

Richard Hayes

Author & Expert

Richard Hayes is a Certified Financial Planner (CFP) with over 20 years of experience in wealth management and retirement planning. He previously worked as a financial advisor at major institutions before becoming an independent consultant specializing in retirement strategies and investment education.

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