A digital nomad working remotely on a bean bag

The New Office - How Remote Can You Go?

  • 1st November 2022
  • 6 min read

There's no question that the opportunity of working remotely has become increasingly popular in recent years. And with good reason - it can offer a lot of advantages, including greater flexibility and freedom, not to mention the opportunity to travel and work from anywhere in the world.

But if you're thinking about working remotely, there are a few things you need to take into consideration, including your budget, the type of experience you want, and how long you can be away from home.

Key things to consider

Before we get into the where, here are a few things to think about when planning a remote work trip:

How long do you want to travel for?

You should also have an understanding of how long you can be outside of your home province to ensure that you don't lose your Provincial Health Insurance Coverage which would also affect the validity of your travel insurance coverage. For example, does your province allow you to be absent for up to 182 days or 212 days? What about the country that you'll be visiting, as some of them have visa requirements and may also limit the time that you'll be able to stay. Regardless of the length of time that you'll be gone, you'll need to ensure you obtain travel medical insurance coverage for the exact period(s) that you'll be traveling outside of your home province.

How do you figure out the budget?

Working remotely can be expensive, depending on where in the world you're planning to travel. Make sure you take into account the cost of accommodation, food, and transit in the location(s) that you choose. But also, what costs will you still be incurring at home while you're gone - such as housing, utility, and car payments? There are additional expenses that you will need to consider, the critical cost being access to reliable internet as well as telephone communications as well as the workspace that you'll be using. Will you be able to access a café, or will you be using a co-working space? These could be part of the hidden costs that one may not readily take into consideration. 

What type of experience do you want?

Are you looking to try out a new city with a similar lifestyle to how you function now? Are you looking to learn a language? Or are you looking to escape winter for sun destinations where you can take up surfing lessons and absorb that Vitamin Sea? Understanding what you want to experience during your travel sabbatical will help determine the best destination(s) for you.

Will you be able to work?

Depending on the type of role one has, we often think that working remotely will enable us to do so much more in our environment, but if you have that 9 to 5 job, will the environment that you're in be conducive to your productivity? Firstly, from a time zone perspective, will you be in sync with your colleagues if there are frequent meetings and fluid collaboration or will you be forced to work at night? For example, if you were in Bali, you'd be almost half a day ahead of your colleagues in Toronto. That's quite the difference. On the flip side of this is of course having structure, so that you don't allow work to consume and you can enjoy time for yourself, to explore and accomplish your goals for the experience that you've invested in.

Destination inspiration for your new office

Once you've determined your budget and desired experience, the next step is to find a location that will provide you with both an inspiring and productive environment. These are some notable places that have been known to accommodate digital nomads.

Yellow tram passing through the streets of Lisbon, Portugal

Puerto Escondido, Mexico

Located in the Mexican State of Oaxaca, Puerto Escondido translates to "hidden port" in English. This laid-back coastal town isn't as overrun with tourists but does offer some fantastic beaches for relaxing as well as surfing.

Lisbon, Portugal

I once heard Lisbon referred to as the "Silicon Valley" of Europe. It's also developed quite a reputation for a welcoming community to freelancers. Portugal's capital city offers a relatively affordable cost of living and is easy to get around. Plus, with its tech focus, you're sure to find great co-working spaces in a setting of much historical architecture.

Austin, Texas

If you're looking for a remote working location in the States, Austin is a great choice. It's affordable, has a robust tech scene with plenty of co-working spaces available, and is also known as the "live music capital of the world”.

A busy street market in Bangkok, Thailand

Bali, Indonesia

Although it may be clichéd at this point, Bali remains a popular destination for digital nomads. It's easy to see why with its beautiful beaches and rich culture. Bali remains relatively affordable, but do think about the time difference if you're going to be maintaining a fluid connection with colleagues and clients based in North America.

Bangkok, Thailand

Bangkok is another popular choice for digital nomads, as it's a city that's easy to navigate and has a variety of accommodation options to fit any budget. There are also plenty of co-working spaces available as well as opportunities to explore Thai culture and cuisine.

Buenos Aires, Argentina

If you're looking to travel to South America, Buenos Aires is a great choice. The city has a rich culture with a European influence and is known for its architecture, art, and nightlife. It's also become quite the destination for digital nomads, as it's affordable and has a variety of co-working spaces. It's also close to most North American time zones so you can keep in step with colleagues back home.

Warren Brown
Author: Warren Brown, Relationship Manager

Warren holds over 19 years of experience in the travel insurance industry. He enjoys telling the stories of people and places which is fed by his love of travel. Warren is an active member of the Travel Health Insurance Association of Canada (THIA) to better educate the Canadian traveller on the benefits of travelling protected.


Sign up for regular updates

Get the latest news, travel tips, and destination inspiration straight to your inbox.