What I Actually Buy for Travel Insurance, and Why

I was on a river cruise through the Mekong Delta in Vietnam when the man from the cabin next to ours collapsed at dinner. His name was Frank. He was from Calgary. His wife made a single phone call and within four hours Frank had been airlifted by medical helicopter to a hospital in Ho Chi Minh City with a cardiac care unit equipped to treat what he was having. George and I sat with her in the corridor while she held her phone in both hands and made calls and answered calls, and at some point she said, with a flat clarity that I’ve thought about many times since: “I’m just glad we got the policy.”

The bill for Frank’s evacuation came to a little over $90,000.

George had already read our own policy that morning. He read policies the way he approached any engineering problem: completely, looking for gaps. He did this at the start of every international trip, at breakfast, before anything else. I used to tease him about it. I stopped teasing him that afternoon on the Mekong.

Why the Math Changes After Sixty

The calculation on travel insurance shifts somewhere in your sixties, and not in ways that are obvious from the brochure. Two things happen at roughly the same time: the trips you take tend to involve more money (longer, further, better), and the health complications that could derail those trips become both more likely and more expensive.

Medicare, for almost all practical purposes, doesn’t cover medical care outside the United States. There are narrow exceptions, but they’re narrow. If you land in a hospital in Portugal or Japan or Vietnam, Medicare isn’t writing that check. Most Medicare supplement plans do cover foreign medical emergencies, but typically to a lifetime cap of $50,000, which sounds like a lot until you’re pricing out a medical evacuation from Southeast Asia. Then it sounds like not enough.

The other shift is in how insurers look at your medical history. Every travel insurance policy has what’s called a “look-back period” for pre-existing conditions, typically somewhere between 60 and 180 days depending on the policy. The insurer looks back that many days from your purchase date and asks: did you have any conditions that were treated, diagnosed, or showed symptoms during this window? If yes, and if that condition contributed to a claim, you may not be covered. This is where most disputes happen, and it catches travelers who assume that “pre-existing” means something obvious like a chronic diagnosis. It can also mean a doctor’s appointment two months ago for what turned out to be nothing.

There is a straightforward way around this. Buy your policy within roughly two weeks of making your first trip payment, before the look-back window extends far enough to catch your full history. Most comprehensive policies offer what’s called a pre-existing condition waiver if you buy early and meet their specific window requirements. It’s not automatic. You have to hit the timing. I set a calendar reminder the day I pay any deposit on a trip.

The premium side is worth understanding plainly too. Travel insurance is typically priced at 4% to 10% of your total trip cost, with the range shaped by age, destination, and what you’re covering. The percentage does rise with age. A policy that costs a 45-year-old 5% of trip cost might cost someone in their late sixties closer to 8%. On a $10,000 trip, that’s the difference between $500 and $800. It’s not trivial, but it’s also not the number to optimize around when you’re looking at the right coverage on the other side of it.

What the Policy Actually Covers

Trip cancellation and trip interruption are what most people think of when they think of travel insurance. If you get sick and can’t go, the insurance refunds the non-refundable portions of your trip. If you have to cut a trip short for a covered reason, it covers the costs of getting home and the unused portion of what you paid.

The phrase to pay attention to is “covered reason.” Standard trip cancellation covers sudden illness, a death in the family, jury duty, severe weather at your destination, and a specific list of other circumstances. It doesn’t cover changing your mind, deciding you’d rather stay home, or general worry about travel. If you want the ability to cancel for truly any reason, there’s an upgrade called “Cancel for Any Reason” coverage, which lets you cancel for anything up to 48 hours before departure and recover 50% to 75% of your prepaid costs. It costs more. Whether it’s worth it depends on how uncertain your trips tend to be at the edges.

Baggage coverage is another place where people discover the gap between what they assumed and what the policy says. Most policies cap individual item reimbursement at amounts that won’t cover replacing a camera, a good pair of binoculars, or a laptop. The per-item limits matter more than the total coverage limit. If you travel with equipment you’d actually need to replace, read those per-item numbers before you buy.

Trip Cancellation Versus Medical Evacuation

Here’s the hierarchy as I’ve come to understand it over four decades of international travel: medical evacuation first, trip cancellation second.

Trip cancellation coverage protects money. Medical evacuation coverage protects your life, and more specifically protects you from having the financial decisions about your life made by someone looking at a spreadsheet in a hospital billing office. The cost of a medical evacuation depends enormously on where you are and where you need to go. From Western Europe, it might run $15,000 to $50,000. From Asia, South America, or anywhere without adequate local medical facilities, a medically supervised air transport to the nearest appropriate hospital can easily exceed $100,000. Frank from Calgary was on the lower end of that range.

Travel insurance policies vary widely in their evacuation coverage, and some include it as part of a comprehensive plan while others offer it separately. There are also annual membership programs, not technically insurance, that specialize entirely in medical evacuation and often provide faster, cleaner service than a standard travel policy’s evacuation benefit. I carry one of these in addition to my regular travel insurance, not instead of it. For international travel without a companion, I consider it non-negotiable.

Primary or Secondary: The Distinction That Matters

This is the one that confuses most people, and it has real consequences.

Secondary medical coverage means the travel insurance pays after your primary health insurance has paid its share. This works fine if your primary insurance covers you abroad. Medicare generally doesn’t. If your domestic coverage doesn’t travel with you, then “secondary” travel insurance is, practically speaking, no coverage at all. You’d be paying out of pocket and seeking reimbursement that may or may not arrive in a useful timeframe.

Primary medical coverage means the travel insurance pays first, without requiring coordination with another plan. The bills get handled. You can focus on getting better rather than managing claims across two insurance systems in two languages from a hospital bed.

I carry primary coverage for any international trip. George set this up originally, after reading something about secondary coverage that alarmed him. It’s the choice I’ve maintained.

Annual Plans for Frequent Travelers

If you travel internationally more than three times in a year, an annual multi-trip policy is worth pricing against individual per-trip policies. Annual plans cover unlimited trips during the policy year, each up to a maximum duration per trip, typically 30 or 60 days depending on the plan. The break-even is usually somewhere around three trips, and the administrative simplicity is its own argument: one policy, one renewal, no gap in coverage if you book something last-minute.

Where annual policies sometimes fall short is in trip cancellation and interruption benefits, which may have lower caps than a per-trip policy customized to a large, expensive trip. If you’re booking a three-week river cruise that costs $15,000, a per-trip policy built around that amount may serve you better than the annual policy’s default limits. For a lot of frequent travelers, the answer is a combination: an annual policy for baseline medical, evacuation, and baggage coverage, with a per-trip upgrade when the stakes on a single trip are high.

What I Check Before Buying

Before I commit to any policy, I look at four things.

The first is the pre-existing condition waiver and the purchase window that activates it. Most comprehensive policies require you to buy within 14 to 21 days of your first trip payment. Miss the window and the exclusion applies. Set the reminder.

The second is the medical evacuation limit. I want to see a minimum of $500,000. For trips to remote areas or destinations with limited medical infrastructure, higher is better. This number is in the policy summary but people often skip past it looking at the trip cancellation benefit. Look at the evacuation number first.

The third is whether the medical coverage is primary or secondary, and whether the policy has a direct-pay arrangement with hospitals abroad. Direct pay means the insurer pays the hospital directly rather than requiring you to pay upfront and seek reimbursement later. In a genuine emergency, you won’t want to be producing a credit card at the nurses’ station.

The fourth is 24-hour emergency assistance: not just coverage, but actual live support available around the clock, with multilingual staff and the ability to coordinate care, manage evacuation logistics, and communicate with your family in real time. When Frank’s wife made that phone call on the Mekong, she was talking to someone who had done exactly this before. That’s a large part of what you’re buying.

The Reason to Do All of This

I want to say plainly what travel insurance is actually for. It’s not a hedge against every bad thing. It’s a way of going fully, without the background calculation running about what you’d do if something happened. That calculation is exhausting, and I’ve met people it has stopped from going at all. That’s not what I’m describing.

What I’m describing is: you buy the policy, you set the reminder, you check the evacuation limit, you confirm you have primary coverage. Then you go. You see Japan in November, when the maples are at their peak and the famous gardens are finally quiet enough to hear what they were designed for. You see Lisbon in September, when the tourists have thinned and the morning light does what it does to the tiles in Alfama. You go with the confidence that comes from having handled the practical things, which frees you to notice everything else.

George was the one who taught me that preparation isn’t the opposite of adventure. It’s what makes adventure possible. I still carry his reading glasses in my bag, in the front pocket where he kept them when we traveled. And I still read the policy at breakfast, in whatever café, in whatever country. Then I put it away and go see what the day has.

That’s the system. It works.