The Great Insurance Hunt Part II | Practical Plans

In the first part of this story, I quit my job to write and travel full-time. When looking for private insurance, I found that comparing insurance policies was a complex and difficult task. In this post I explain how I narrowed down my options and identified the most important items in a policy, and picked two policies that suited my situation.

I had to choose between two types of insurance: travel insurance and expatriate insurance.

Travel insurance offers limited medical and theft benefits, but is very affordable. Expatriate insurance offers much better benefits, similar to those that people receive from insurance companies in their home countries, but is much more expensive than travel insurance.

It was easy for me to compare travel insurance policies because there are few that are tailored to long-term travelers and cover outdoors adventure activities like surfing and paragliding, and the other things I planned to do. The travel insurance policies that I found cost between $50 and $100 USD per month.

It was very hard, however, to compare expatriate insurance policies. Many companies offer them and the prices, benefits, and exclusions varied greatly. After some searching, I stumbled across, a website that allows you to compare international health insurance policies side-by-side the same way Expedia allows you to compare airline tickets.

After comparing several expatriate insurance plans I realized that they probably weren’t appropriate for my situation. Although the coverage was good, the terms of most were fuzzy with regard to things such as having belongings stolen while traveling. Expatriate insurance plans are mainly designed for expatriates who require quality medical cover while living away from their home country and not for somebody like me who needs additional cover for expensive photography equipment.

So, travel insurance it would be. I first looked at travel insurance from Unfortunately, I found a disclaimer in the policy that drastically reduced my medical benefits if I did not have government health care in my home country, Canada. Since I spend more than six months each year outside of Canada, I’m not eligible for Canadian health care. So, World Nomads was out.

After some searching I came across STA Travel. I spoke to an agent who assured me that my lack of Canadian health insurance would not be a problem and that they would cover me for all of the outdoors sports that I planned to do. It only cost $55 per month so the price was right.

There were two problems though. First, if I was seriously hurt or sick they would pay to bring me back to Canada, but then I would be on my own. So, if I got into serious trouble, I would have to pay my own Canadian medical bills for the first three months I was in the country (after that I would qualify for Canadian health care).

Second, the theft policy would not fully cover my expensive laptop and camera should they be stolen (few travel insurance policies fully cover these items). I asked around on some travel blogging forums to find out how others dealt with these problems. They referred me to a specialized insurance agency that offers special travel insurance for specific items. Through that agency I was able to insure my electronics for about $150 per year.

So, although I was not able to find an ideal insurance solution, I found one that seemed OK. My electronics were insured. I would be taken care of in case of a medical emergency. The only problem is that if something goes terribly wrong, I may end up with three months worth of expensive Canadian hospital bills. But, to be honest, I could not find a better option.

But, since I’m only paying about $70 per month for insurance, I think the risk is manageable.

Header photo: olarte.ollie

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4 thoughts on “The Great Insurance Hunt Part II | Practical Plans”

  1. mmmh – so you are without “proper” health insurance if I understand correctly…

    I have exactly the same sort of issues that I had when looking for insurance for my RTW trip and am more or less in the same situation (except that I have left the UK for less than a year so I am still covered there for now)

    I do not know what to do after the first year though.

    There is a reason why you usually pay a relatively high part of your salary in social contributions in any country (and why you can benefit from social security, health insurance, etc.). If you want to get the same level of protection, I would expect to have to pay quite a lot too – otherwise you are not covered for all the “expensive stuff” hence the travel policies are cheap…

    Let’s say you lose a leg in an adventure in an under-developed country (worst-case scenario – but, heh isn’t it why we take insurances). Local hospital might do a sh**tty job of trying to fix it. You get repatriated home and all the costs pertaining to hospital, operations to fix it, rehab, etc. fall onto you. Not an attractive proposition.

    The main difference between the standard health coverage in a home country and while traveling on a long-term basis seems to be that in the latter case the contributions are “voluntary” making it somehow harder to “swallow” than in the former case where social contributions are automatically deducted from your income.

    Thanks for posting this article anyway – good resource on the link to that broker.


    PS: I am actually going to be in Taiwan next month (and found your site looking for info on kitesurfing) – would you have any recommendations on good spots to learn on the East coast?

    • Hey Jezza,

      I understand your reasoning about health care prices, but I have to disagree with your logic. In Canada full coverage under our Medical Services Plan would cost me $60 CAN per month–slightly more than I now pay for travel insurance.

      It is true that that cost is subsidized by taxes. However, I would have no problem paying Canadian taxes on my income if I were eligible for health care there (I currently have non-resident status and don’t pay taxes, but even if I declared residency and paid taxes I would still not be eligible for health care). I looked into this option while in Canada last summer, and even petitioned to challenge the legislation that prevented me from being covered, but was unsuccessful.

      So, I have definitely considered the full cost of national health care as compared to expatriate insurance and travel insurance. The truth is that expatriate insurance is simply more expensive. This is not surprising. Private insurance is nearly always more expensive that public because the former must operate with a profit margin while the latter is able to break even or even absorb regular losses.

      Brokerfish is very useful, though, if you are looking for good expat health insurance. It was definitely the best resource that I found.

      As for kitesurfing, I’m afraid that I don’t know of any place on the east coast with an English-speaking instructor. I’ve heard that there is a club in Taipei with a lot of members. It’s likely you could find lessons there.

      The teacher mentioned in the article you read now lives in Taichung. I’m not sure if he’s currently teaching, but he’s a very helpful guy. His contact info should still be correct. I would recommend asking him.


  2. Hi Matt,

    Can you give me the name of the theft insurance you ended up going with? I’m having the exact same issue 🙂


  3. Hi Brandy,

    There’s a company called Clements ( from the USA that allows you to insure specific items. You can do it using their expatriate professionals abroad coverage. It’s meant for expats moving abroad, but travellers can also use it. You may have to give them a call to get it worked out.

    I hope this helps!



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