You can live here and work remotely for a company in another country, for as long as 12 months. While you’re here, you can start an application to immigrate.
Canada does not have anything official for digital nomads: a formal visitor’s visa allows you to work for a remote employer for up to a year. It used to be six months, but that was increased.
You’re going to be here longer than 180 days, so you will need to pay for a visitor’s visa. That is done by filling out a web form, providing information and paying the fee with a debit or credit card.
https://ircc.canada.ca/english/information/applications/visa.asp
The requirements for a visitor visa includes:
•Valid passport.
•Proof you work with a foreign employer.
•Proof of financial support (ie, bank records).
•Purpose of visit documentation.
•Evidence of intent to return to home country, like an airline ticket or having a home in the US.
•Have a valid health insurance policy covering your entire stay in Canada.
•A possible medical examination.
•A possible background check.
You should get a detailed letter from your employer saying what you’re going to be doing, and saying that no Canadian work will be done.
A visitor’s visa is a “single-entry” visa. There is also a “multiple-entry” Temporary Resident Visa (TRV), which you can pre-request.
This uses the same process as getting a single-entry visa: you say you’re a digital nomad, that you’ll be visiting regularly, and that you want a multiple-entry visa. That seems to go in the “purpose of my visit” and “other” fields of an Application for Temporary Resident Visa (IMM 5257) form.
https://www.ircc.canada.ca/english/helpcentre/answer.asp?qnum=417
These typically are valid for up to 10 years, and allow you to cross back and forth. You still have to meet the requirements and stay for a limited time per visit, but these make it clearer to the immigration officers when they find you entering Canada repeatedly.
Each time you enter Canada, you’ll need to show customs your visa, say that you’re a digital nomad and answer their follow-up questions, so they know you’re legit.
By the way, if you’re thinking of leaving, pulling a u-turn in the middle of the Ambassador bridge and coming back, don’t. That’s just a tiny bit suspicious (:-)). Instead, consider being a “snowbird”: live in Canada in the summer and somewhere warm in the winter.
From inside Canada, you can apply to stay longer, which is called “applying for a visitor record”.
https://www.canada.ca/en/immigration-refugees-citizenship/services/visit-canada/extend-stay.html
You can do this for a TRV as long as you do so before it expires.
Many other countries have digital nomad visas: more information is at Wikipedia, in https://en.wikipedia.org/wiki/Digital_nomad
There are at least two books about being a nomad:
The Digital Nomad Handbook by Lonely Planet, as an a eBook is available from Kobo at https://www.kobo.com/ca/en/ebook/the-digital-nomad-handbook?sId=1a9f88fe-7812-4629-82cd-d4a4dda709d9&ssId=OK6scrhYzg1HX1yjSsmKI&cPos=1
Amazon has that and Digital Nomads For Dummies (English Edition), in several formats.
This is a live document. These links will change. Always refer to the government pages for current rules. And please file an issue at https://codeberg.org/tokugawa-behr/Fleeing-to-Canada/issues so I’ll know what needs updating.
You can live here and work remotely for reasonable periods, and get an application for permanent resident started while you’re doing that.