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Canadian company. I was wondering the legal aspects of working online in a different country. Assuming you have manager approval, timezone differences accounted for, stable internet connection, etc.. Is there anything to look out for regarding the laws in Canada and in an European country.

I know for extended stays there are tax implications and visa requirements (30 or 90 day) but what about short term stays in multiple countries?

Example. Working in England for 3 weeks then going to Sweden for 3, belgium, etc.. Is there a max time I can be out of country?

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    With your manager's (written) approval you can even devote your whole days to eating and burping and get paid for it.
    – BigMadAndy
    May 7, 2020 at 21:44
  • max time before what? Before they take away your citizenship?
    – Kilisi
    May 7, 2020 at 22:02
  • @Kilisi Being out of country and in other(s) May 7, 2020 at 22:03
  • what do you worry about? Immigration, career, taxes? it is unclear what are you trying to achieve or prevent May 7, 2020 at 22:38
  • visa's are going to be more of an issue than your comment implies you think that they are. You can't legally work on a tourist visa; and most developed countries are picky enough about who they let have work visas that just hopping from hotel/etc every few weeks isn't going to work. May 7, 2020 at 23:16

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Is there a max time I can be out of country?

Health coverage is based on physical residency

If you are out of your province for too many months, you can lose your health insurance. You generally (this differs by province) need to be physically present at least 183 days of the year. There can also be reporting requirements for being outside the province for times under that.

Also, many Canadian travel insurance policies are based on your provincial coverage picking up some of the tab. If you lose your provincial coverage, that medical policy can also become invalid.

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On Travel Stack Exchange we have several questions about working from others countries, as digital nomad or just a holiday maker who has to work a few days. And more are on Expatriates Stack Exchange.

Your home country mostly does not mind, as long as you keep paying your tax, but have to check whether you need to pay, out of your pocket, things which would normally come from your wage payments, like retirement funds and future social security payments. And of course, whether you will still be in a national or state organized health insurance.

In general, most countries do not yet have the rules adjusted to the modern 'can work from everywhere' situation.
As far as I understand most countries do not allow work without having a work visa. The UK is certainly on that list.

Of course, most people who move around and never stay in a country longer than a few weeks will not found out, but if you are found out you will run into trouble.

At this time, I would not advice you to travel and 'work from home' wherever you happen to be, as the laws are not (yet) adjusted to it. And besides, you will not be able to see much from the countries as you will need to be working pretty much full time.

That is not taking Covid 19 in account, for this summer traveling around is going to be restricted and it is unsure how it is going to progress.

Privately organized healthcare insurance has been available for a long time and it is unlikely to be discontinued in the future, but you may have to jump through a few hoops to get it sorted.
Most countries expect you, as Canadian, to have good links to your country and do grand you tourist leave to enter, mostly 3 months or even 6 months at a time. But be aware of the restrictions. For most of Europe you will get entry into the Schengen area, and that is for a 90 days in any 180 days period. That means that you can not stay in the area for more than 90 days in one go, but you can go out and back in, as long as you do not get over that 90 days limit.
But the more often you move around, the more likely some border official will want to check out details and if found working illegally (even for a company back home) according to their laws, your trip will be over and you may face a tax bill for the time you have been in the country before.

If you are serious about your travel plans, best check it out online, or come to either Travel Stack Exchange or Expatriates Stack Exchange, where the concentrate on longer stays and are more familiar with work visa.

As there are differences between countries, best think up a list of countries you would consider traveling to.

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