Should Frequent Travelers Buy Travel Insurance? Is My Approach Wrong?

OMAAT reader James asked if I’ve ever written about my approach to travel insurance. As he asked, “not sure if you ever buy it sporadically or have an annual policy, but you’ve been to some pretty far flung places, and I’m curious how you protect yourself and your family when you travel.”

Well, I don’t think I’ve ever addressed this in a post before, but I have a confession to make… and I hope to learn something from the comments section of this post!

I don’t typically buy any sort of travel insurance

I don’t think I’ve ever deliberately purchased travel insurance, believe it or not. Maybe I take too much of an “out of sight, out of mind” approach to this. I can’t say I’m familiar with travel insurance policies in great detail, though generally speaking, I tend to think they fall into one of several categories (with a huge amount of variability, of course):

  • There’s the type of travel coverage you may get with credit cards, for things like rental car coverage, lost luggage, delayed flights, emergency evacuation, etc.
  • There’s more health insurance focused coverage, for any sort of illness or hospitalization that may happen abroad
  • There’s travel insurance that covers things like trip cancelation due to illness, or some policies even allow travelers to cancel their trip for any reason, and receive reimbursement

Typically, my approach has been that I try to strategically use credit cards that offer certain types of travel coverage, for rental cars, delayed bags, emergency evacuation, etc. Beyond that, though, I haven’t really purchased coverage. Why?

  • Since I often use airline and hotel points for my travels, that gets complicated in terms of potential reimbursement with these policies, and it also gives me more flexibility, since these kinds of reservations can often be canceled until close to departure
  • While the concept of a “cancel anytime” travel insurance policy sounds great, they’re typically astronomically priced for obvious reasons
  • So my only concern would be for some sort of a health emergency outside the United States, though frankly healthcare is usually so much more reasonably priced abroad, so it’s not something I put much thought into
  • I generally find insurance to be a hassle, given the terms, conditions, restrictions, etc.

I tend to think that insurance policies are important for things you couldn’t reasonably afford to fund or replace, like major damage to a home, treatment for a long term illness, etc. But when it comes to things that could reasonably come up when traveling abroad, I think that I’m lucky enough to have a safety net where it’s not worth spending extra money to be protected in that way.

Similarly, I can understand wanting travel insurance if you’re planning a once in a lifetime trip, or something, but for me, travel is a pretty consistent part of life.

Maybe I just don’t know much about travel insurance?

How do other frequent travelers approach travel coverage?

The above is the approach I take, but that’s not to say that it’s the correct approach. If anything, perhaps my luck with traveling so far has made me not consider this, when it’s something I should put more thought into, especially with an increasing amount of family travel. Perhaps I’m just in the “ignorance is bliss” camp.

So I’d love to learn from others. What approach do you take with travel insurance policies? Is there some sort of annual policy that makes sense, especially for those of us who frequently redeem points, and as a supplement to the coverage we have on many credit cards? Or are there per-trip policies that it makes sense to purchase?

Is there a policy for frequent travelers that makes sense?

Bottom line

I love when I’m asked questions I simply don’t have answers to, because it gives me an opportunity to learn. While travel insurance is a massive industry, it’s one that I’ve not put much thought into. I hope that the limited coverage provided by my credit card will provide some value, but other than that, I’ve never really purchased a policy.

To fellow frequent travelers, where do you stand on the concept of travel insurance? And to those who use it, how do you do the math on it?

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FoulOwl Diamond

Ben, never ever ever do I purchase it…. unless it’s an absolutely huge non refundable booking and none of my credit cards will cover the loss. What I absolutely do pay attention to is the fine print on the various credit card trip cancellation coverages. Here is a good example: I was chartering a boat down in the BVIs and my deposit was significant and non refundable. My major concern was if there was a hurricane that came through and prevented me from taking the trip. When I looked at my AMEX card I realized it would NOT cover a loss due to a named storm, however when I looked at my Chase sapphire reserve card I saw they do cover losses due to named storms, up to $10,000. So I booked the nonrefundable deposit with Chase. Sure enough three months later a hurricane took out most all of the BVIs and the boat I charted… my trip was canceled, and as expected, the charter company would not refund my deposit per their contract force majeure clause. Chase took care of me and paid me back for the full deposit. If none of my credit cards had that coverage, then that is the one time I would probably get travel insurance.

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Ryan Guest

A lot of comments but not a details from folks detailing which providers they use and whether the claim process went smooth or a complete circus. Like Ben, I never purchased medical insurance before. After potentially dodging an appendicitis in the Bahamas by a few days, I looked at it for my first extended Europe trip and must say, not the easiest to find medical only plans let alone repatriation never showed up.

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eliashan Member

Kinda shocked to read this naive approach to international travel. A frequent travel blogger without travel insurance (at least med) is the equivalent of a sex worker not using protection or having themselves checked regularly. Completely reckless. Why risk paying even 10k out of your pocket (I won't even say 100k or 1m that are also quite possible) when you can avoid this for a couple of hundreds bucks a year? That's less than the fees you pay for a one-way award ticket, it's just ridiculous to even debate this.

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Joe Johnson Guest

It really amazes me the difference in ways of thinking between millennials like myself, 44, and these ...elderly folk. so...despite 44, my mother is Portuguese so ive spent summers there since 1, dads side Canadian and im dual citizen so many trips there til adulthood, studied abroad in Italy, MBA in Paris, about 100 trips to europe, Mexico, abroad etc etc etc ....despite my study abroad trip, never bought insurance for travel. ur plan will cover, the country covers, plus CC stuff...its a scam. its socialistic healthcare btw. ur not getting a big bill. what credit score are they hurting btw? it seems boomers, im guessing white boomers, are the main, like so so so many, sources of revenue for these. which is great! I support people propping up economy on dumb ass things while others dont.

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Elteetrav Guest

I join the many others here who say you need to buy a travel policy that covers emergency medical and evacuation costs. I have an annual policy that covers anny number of trips per year for less than $325 (I am 69 years old. Your price would be less.) The only challenge I have had is that the policy only covers trips of up to 70 days each, so I am careful to get myself back home within that time frame. But you take lots of shorter trips, so that would not be a problem for you. I totally agree that buying insurance for cancelations, or lost baggage, or similar expenses that are either covered by credit cards or could be absorbed on your own is not generally necessary. Though people should think carefully about their own health situation and ability to handle unexpected costs. For example, as I get older I do think more about buying coverage that would cover cancellation costs if I had to cancel for health reasons. I haven't bought it yet, but if I book a very expensive trip I would seriously consider it. Thanks for all your excellent posts.

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