Travel Insurance: A Worthwhile Gamble?

Offering a pen to sign a contract to someone who is pensative with closed hands.

Insurance is a gamble. By definition. Literally.

The Deceptive Unknown

As a responsible adult, it’s your responsibility to objectively evaluate whether the gamble of insurance is worth it for you.

When you first start out traveling, I advise you accept your limited ability to do this objectively. This isn’t a comment on how smart you are or anything like that, but simply that you don’t know what the lifestyle will entail – and what you will choose to make of it – if you haven’t lived it before.

No matter how much you’ve researched it, or watched videos/followed instagrammers, you won’t fully understand the lifestyle until you’ve lived it.

Content created by instagrammers or influencers can be its own problem because a lot of people have a vested interest in misrepresenting the highlight reel as the entire show, especially on social media.

As such, you would be gambling in a game you have no idea about, and the objectively responsible thing to do there is protect yourself.

The Initial Adjustment Period & Unavoidable Learning Curve

Almost all of the accidents and major issues I’ve had in my travels happened in the first 3 years, and almost all of those happened in the first year.

I really wish I had paid for insurance at that point, as I not only had to pay out of pocket for what happened – and there was a lot – but sometimes, I had to settle for less than what future-me would have accepted in terms of treatment, because I just could not cover the out-of-pocket expenses for the things that were not absolute necessities.

This is especially compounded if you’re starting in your early 20’s (like I did), when you are still under the illusions of invincibility and your infinite wisdom, before life has slapped you upside the head a few (dozen? at least) times.

Like What You See?

We send exclusive tips & resources, daily, by email, for free, on how to create the freedom to travel full-time, and optimize the quality of your travels.

What happens after that initial period is that you get into your groove of traveling: you discover the kind of lifestyle you live, the elements and risk factors that play a part, including the parts that are indiscriminate of (but of course, can be affected by) lifestyle, i.e. you, your age, health, etc. – the “traditional” factors that would go into this consideration without adding travel to the mix.

Getting a Handle on Your Unique Lifestyle Variables

After that initial 3+ year period where you are figuring out how you like to stand, walk, run and fly around in this big wide world – when you start to notice patterns, while still giving it enough time to be able to get your balance – you then re-evaluate whether the lifestyle you gravitate to presents significant enough risk to necessitate the cost.

Could You Cover It? Would You Want to?

There are factors in this beyond the external lifestyle, meaning for example, without insurance, could you really cover something major that would happen, out of pocket?

This can be a difficult question (well – answer) to come to terms with if you’re not making good money, as the monthly premium seems like a lot, and you can be tempted to risk it – that is where the evaluation of how you live your life day to day comes into play. The reality is that you may be put into a situation like the Tiger King where you “will never financially recover from this”; and remember, that’s not just about you, but the people around you, including the ones who may be affected by such an accident, if it’s found to be your fault.

On the other side of the coin, even if you could cover it – a situation where you do have more than enough to pay whatever monthly premium – would you want to?

Medical Tourism as a “Kind-of” Option

Another consideration is the reality of medical tourism: there are lots of places you can fly in, get exceptional quality healthcare in the moment with cash, and pay far, far less than you’d even fathom, without having local health coverage.

This is a potentially massive rabbit hole that depends largely on what you want done, and probably isn’t applicable in the case of many emergencies – which is in large part one of the primary domains of risk you have to evaluate with insurance.

Insurance Providers Denying Claims

Even if you have travel insurance, having it serve its actual, core, purpose, is not guaranteed.

Part of the risk or gamble of getting insurance is that the insurance provider won’t pay the claim. There are plenty of horror stories across the public internet, private facebook groups, and individual travelers you meet – which specify companies by name, including, for sure, the one(s) you’re considering.

So even if you have it, be prepared to fight for your reimbursement, and make sure you are very clear on the limitations and processes of your policy, both in terms of what you’re covered for, and how – like if you need to go to affiliated hospitals only, if you are covered if you pay the costs upfront (or have to wait for them to approve it, which can be a really stupid proposition/process in case of emergency), and keep copious amounts of paperwork (and be prepared to travel with those documents) including your patient history at your hospital.

After You’re Acclimated

3 years is still not that much to have traveled – as weird as that sounds, though of course that depends upon the person.

I notice that 3 years happens to be a common marker of time when the novelty of travel has given way to a more integrated and realistic view of travel – not entirely “given way”, but at that point, novelty is no longer so much the sole/primary motivator or area of focus – and when people start to evaluate more clearly how they plan travel to fit into their lives going forward.

Some call it quits, others keep it going – and not necessarily in the same way – but I have encountered many people who introduce some kind of change at that point, first in the way they see travel, then pretty soon after, they way they fit it into their lives.

That sort of inflection point, although it’s not the same for everyone, often brings along certain things with it, the specifics of which also vary from person to person – though this subject is way beyond, yet related in part, to what we’re talking about here.

Thinking about insurance, and referencing the “integrated and realistic view of travel” one gets around that inflection point, whenever it is, you get the idea of what you want travel to be for you, and where you want it to fit in your life, with an understanding of how it can actually be done (by virtue of having done it).

These are decisions we each have to come to terms with for ourselves.

Even when you make that decision for yourself, I advise at that point to still give it a year (of having insurance) to evaluate the reality.

Taking Travel (Insurance) Into Your Own Hands

If you find that the kind of ongoing travel you can predict you’ll be having – and predict is the operative word here, since we’re talking about gambling – is one where the odds will be in your favor (again concerning your own personal factors that play into the equation), you may choose to opt to bet on the option of medical tourism (which of course you can still do while having insurance) and a low-risk lifestyle.

On the other hand, the type of travel you may want to have more consistently dangerous circumstances – looking from an objective view, and, importantly, absolutely not taking the “well I am good at X and therefore probably/mostly invincible” stance – and you may use that as sufficient risk to warrant covering yourself from all sides possible.

One part of this, for example – this point in time – is that a lot of people have sewn their wild oats and calmed down a bit (plus matured both through the natural process of time and the accelerated process of travel), and also are looking for a way to pace themselves with the perhaps new realization “in their bones” that they really can do this forever if they want, and so tend to chill out a bit.

When Especially to Not Rule Out Insurance

How risky your lifestyle is is far from the only factor (again, personal history, age, all that – plus just random chance and you being risk-averse and flush with cash – to name but a few), but it is a good initial threshold test, especially in the negative.

If you are doing dangerous stuff, or if you are uncertain of what you will be doing, (and in the beginning it’s usually both), get insured, is my strong, strong advice.

Future you will be thankful, and hopefully, if you’re lucky, for nothing else than the peace of mind.

Beyond that, you make your decision, but be objective.

And, I’d advise you to err on the side of caution.

Get Quick Answers to Top Long-Term Travel Questions!

Inside this frequently-updated report, you'll find the direct, to-the-point answers to the most commonly asked questions about long-term & full-time traveling.

Enter your name & email to get your free copy - and learn how you can get your own top questions answered (for free!) as well.

Get Quick Answers to Top Long-Term Travel Questions!

Inside this frequently-updated report, you'll find the direct, to-the-point answers to the most commonly asked questions about long-term & full-time traveling.

Enter your name & email to get your free copy - and learn how you can get your own top questions answered (for free!) as well.