Traveling Constantly: Buying Travel Insurance for more than 30 day trips

I thought I’d do a quick post today about travel insurance.

I was informed by some good friends recently that we should really consider purchasing it, because even though we are covered under universal healthcare in Canada, when we leave Canada, it’s a whole other ballgame.

(This is NOT a sponsored post, and this is not me trying to sell anyone anything, it’s me realizing that we need protection if we’re outside of Canada.)

If you travel a lot, you will need to buy travel insurance just in case something happens.

What could happen?

  • You get stuck in a country and suddenly a civil war happens or a natural disaster hits
  • You are across the border shopping and someone runs you over and you need emergency medical assistance that comes out of pocket
  • You are traveling in France and you fall and accidentally break your jaw and need emergency dental care

All of this stuff comes out of pocket if you don’t have travel insurance.

People might see it as a waste of money but it covers you JUST IN CASE something happens and you need immediate assistance without going bankrupt afterwards.

Our traveling background

We’re people who travel constantly for work and for pleasure.

We go all around North America but also overseas for months at a time.

Our trips last anywhere from 10 days (minimum) to 6 months and trying to find travel insurance was a real pain in the butt to cover people like us.

Why it was a hassle for us

Most people take a trip for a week or two, perhaps a month at the max.

Us, we could travel the whole year moving from city to city and not come back to our “home city” except once every 6 months or longer.

Most travel places only offered 10 days, 30 days, or 60 days coverage at the max, but any day after 60 days and you were on your own to pay PER DAY for extra extended insurance.

How much our general online quotes/searching cost

We checked everyone from CAA to Manulife to Mondial Assistance to Blue Cross and their plans are just not suited for super frequent travelers like ourselves.

They quoted us about $100 or less for a general “yearly” plan, with trips that can range up to a MAX of 30 days.

However for extended insurance, like traveling 35 days to Asia, the last 5 days would not be covered under that plan, and we’d have to pay PER DAY past our regular coverage.

We are also planning on traveling for about 6 months for the end of this year, and our final quote was around $900 for me and $1000 for him. So about $1900 in total for 6 months!

Their definition of a “Trip” was also sketchy. If you rented a car, it wasn’t a “Trip” any more for some of these agencies.

Who we finally settled with


We wanted a company that would be big enough to pay out in case we needed it.

We wanted a company that had multiple options.

We didn’t want to pay $1000 each.

We went with their International Coverage because we weren’t going to war torn countries, but if we were, we’d take their Majestic coverage.

For our two trips lasting 36 days and 43 days, it was about $190 for the both of us a the International coverage. Majestic was up there around $225 for the both of us.

For our trip that will be about 6 months, it was $400 for the both of us.

To go from a $1900 quote to a $400 one, is pretty amazing!

So that’s our little adventure with buying travel insurance when we’re traveling constantly for a year and for a long period of time.

What do you do when you travel?

About the Author

I'm a 20-something year old girl who lived out of a single suitcase in 2007, and now I'm living with less, but only with the best. You don't have to get rid of everything to become a minimalist! Minimalism can help simplify and organize your life, career, & physical surroundings. You can read more about me as a minimalist. Or come and visit my other blog Fabulously Broke in the City where I got out of $60,000 of debt in 18 months, earning $65,000 gross/year.