Remote work has opened a whole new world - literally - for many Canadians who love to travel but have a limited number of vacation days. The practice even has its own name now, dubbed the “workcation,” where an employee packs up their laptop and travels outside their immediate region or country while still clocking in eight hours per day at their job.

While getting your work done from a beach or a café in Europe might sound appealing, it’s emerging as a potentially contentious subject between bosses and employees in the era of remote work.

“There isn't anything specifically that employment legislation speaks to with respect to remote work frankly, or your right to work remotely. So we're really walking into new territory here when it comes to the right to remote work and where remote workers can do their work,” said Sunira Chaudhri, founder of employment law firm Workly Law, in a phone interview.

While some Canadians took advantage of full-time remote work and worked from anywhere early in the pandemic, she said now that offices are starting to reopen, employers might be stricter about where staff can work.

“I think what we're going to see now though, especially for employees that are in some way client-facing, in some way team-facing … I think we're going to see a lot of restrictions around where you can complete your work, especially if you are hybrid or remote working,” Chaudhri said.

A December survey, referenced by the Canadian Press, from vacation booking company Kayak found one-fifth of working Canadians and 38 per cent of young workers planned on taking a workcation this year. The survey polled 1,000 Canadians.

Chaudhri said “employers have close to absolute discretion where you do your work,” while acknowledging that employees were able to work remotely at the height of the pandemic due to “exceptional circumstances.”

For those employees who are now essentially prohibited from working from anywhere, there’s likely little they can do from a legal standpoint to fight company policies.

“I believe the courts don't like to really wade into the waters of dictating how a business should run itself. So if you as an employer, you as a business, dictate that it's a reasonable business decision that you need your staff in office, or on premises, or on site, I think your employees are going to be hard pressed to prove to a judge that's simply not the case,” she said.


Chaudhri said employers could also make an argument for needing staff in the office because of the intangible elements of an employee’s presence.

“It could be meeting a client for lunch, it could be mentoring a new employee, it could be onboarding — a lot of these lighter touch components that might not seem integral to your role, but you kind of did as part and parcel of your role pre-pandemic,” she said.

“Now we're sort of looking at those elements of our roles under a microscope and seeing what really is necessary.”

For those who are able to work abroad, time zones could present challenges – which is what Christine Simone, co-founder of U.S.-based health-care services startup Caribou, found. The fully-remote company has a small number of employees in the U.S., four employees in Canada and contractors in South America, Africa and Europe.

As a co-founder, she has set a workplace policy that allows team members to work from anywhere, so long as the work is completed and they’re able to join on-camera meetings when necessary.

“We’ve told employees that they can either take vacation when they want to go travel, or if they can ensure that they have the ability to work the same amount of hours — it doesn't necessarily need to be the same hours of the day — but the same amount of hours to get the same amount of work done and have good Wifi and be able to join team calls and do on-video, then they're able to do that from anywhere so long as they're keeping their tax situation in mind,” she said by phone.

While Simone is based in Miami, she chose to work remotely from Rome and Mexico for a combined eight months.

She said she found communicating and coordinating with clients in Pacific and Eastern time zones challenging and she sometimes worked late into the night while in Europe to be available for North American clients.

However, there were aspects of being in a different time zone that were beneficial, like the ability to work through the morning in Italy and not be interrupted by meetings and client calls since it was nighttime in the Western world.

“I was able to have that kind of workcation, or remote work from a different country, and experience different cultures and different environments. And that was really amazing,” Simone said.

She quickly figured out she could schedule emails and notifications on messaging apps to coincide with the time zones clients and coworkers were in.

Overall, she would recommend taking a workcation to anyone who is able to.

“It is an amazing experience. And I think that it's something that might be short lived. So take advantage of it now while you can,” she said.


For Canadians who take advantage of working abroad while being paid by a Canadian employer, tax implications will come into play around the six-month mark. It’s referred to as the 183-day rule by tax experts.

“In the case where you are [working for] more than 183 days [in another country], your income is not exempt from tax in the other country. You are nonetheless able to claim a foreign tax credit on your Canadian return but that's why most people will not leave for more than six months,” Josee Cabral, senior tax specialist at H&R Block, said by phone.

Cabral said Canada Revenue Agency will also judge your residency status to determine how your income taxes should be treated in Canada. The CRA takes into account your ties to Canada including whether you have a Canadian driver’s licence, property and family ties, among other factors.

“If you leave and you're abroad, but you still have your Canadian bank account, and your money's being deposited in your bank account, and that’s your current bank account, then you still remain a resident of Canada — and you have to pay income tax and you have to file income tax in Canada,” she added.


While companies like Caribou allow for workcations, other companies may not. For those who take it upon themselves to relocate anyway, employment lawyer Chaudhri warned there could be a range of consequences.

“I think you can certainly get fired for traveling if you're prohibited from traveling while working. I think you could see some discipline. … I don't know that could give rise to cause for termination, but it signals dishonesty,” she said.

“If you go against company policy, that is one thing, but if you also conceal the fact that you've done it, I think that's another issue where, you know, especially when you're working remotely, employees can take for granted that trust is a commodity.”

”If you breach that trust by concealing the fact that you're working abroad, I think that might really undermine that trusting relationship that must exist for remote work to be successful in any organization,” she added.