Where can I travel for prolonged periods of time while legally working remotely for a company in my home country?

There's one place where an American citizen can work completely legally and indefinitely on a tourist visa: Svalbard! Under the terms of the Svalbard Treaty, any citizen of a treaty signatory, including the US, may "become residents and to have access to Svalbard including the right to fish, hunt or undertake any kind of maritime, industrial, mining or trade activity." Thanks to the Svalbard Undersea Cable System, it also has excellent Internet connectivity at a blazing 2,500 Gbit/s.

Welcome to paradise! Shown here in summer. (Photo mine.)

Now, there are a couple of minor catches...

1. Located at 78°N, Svalbard's main town Longyearbyen (pop. 2600) is by far the world's most northernmost civilian settlement, and rather resembles Mordor after it has frozen over: lots of black rock, virtually no plants larger than lichen. This means an average February day is ?21°C, a balmy summer day in August is 3°C, and oh, there's no sunlight whatsoever during the polar night between late October and mid-February. Also, you need to carry a rifle if traveling anywhere outside the town due to the large and hungry polar bear population.
2. The only practical way to get to Svalbard is Norway, which can and does enforce its own visa rules. That said, once there Norway and Schengen rules (eg. the 90-in-180 limit) do not apply, all you need to demonstrate is that you have the means to support yourself.
3. Essentially all private accommodation on Svalbard is owned by companies in Svalbard, which means finding a place to rent is tough to impossible. Now you could just stay in a hotel, but...
4. If you thought Norway was expensive, imagine Norwegian prices with a hefty bonus for shipping everything through some of the roughest sea on Earth. You won't get much change back from US$20 if you buy a kebab and a Coke.

So hey, it's not exactly a tropical paradise island, but at least working there is perfectly legal!

Canada! Here's what the Immigration, Refugees and Citizenship Canada says about What kind of activities are not considered to be “work”?:

long distance (by telephone or internet) work done by a temporary resident whose employer is outside Canada and who is remunerated from outside Canada;

I can heartily recommend Beautiful British Columbia, especially Vancouver. It's a fantastic mix of untouched nature (did you know there is still first grown forest within the boundaries of Greater Vancouver?) and a modern North American metropolis with all that it entails. Do not listen to those who say it is a no fun city.

I'll answer specifically for the UK, implicitly for the EEA because there are intersecting regulations...

For reference purposes, the rule at the time this question was asked was...

does not intend to produce goods or provide services within the United Kingdom, including the selling of goods or services direct to members of the public; and

The rules have been changed TWICE since then. This rule is no longer part of the current rules and is maintained only in archived form at Archive: Immigration Rules. The text is important because some of the same language and concepts (intent) were carried forward into subsequent legislation.

Immigration Act 2014

The visitor rules were changed in the above act and became active in 2015. As a part of this change, the 'Permitted Activities List' was introduced. The relevant part of of the rule itself is in V 4.6...

V 4.6 Permitted activities must not amount to the applicant taking employment, or doing work which amounts to them filling a role or providing short-term cover for a role within a UK based organisation. In addition, where the applicant is already paid and employed outside of the UK, they must remain so. Payment may only be allowed in specific circumstances set out in V 4.7.

And the relevant clause from V 4.7...

V 4.7 The applicant must not receive payment from a UK source for any activities undertaken in the UK, except for the following:

Immigration Act 2016

This act added a new criminal offence for unlawfully working in the UK if the person knew or had reason to believe that they were disqualified from working because of their immigration status.

The act further clarified what types of work were prohibited and includes entering into contracts to provide goods and services and entering into contracts to perform work as self-employed. The act specified that 'contracts' can be formal documents or verbal agreements. The act further allows the government to seize amounts in excess of £1,000 under the Proceeds of Crime Act 2002.

Despite the broad redefinitions of 'work', the visitor rules themselves were not changed as a result of this act.

Documents

The latest version of the rules are in Appendix V.

Guidance is at Visit Guidance.

COVID-19 made remote working more mainstream and more and more countries with their economies badly shaken finally wake up to the fact that digital nomads are not illegal workers but a source of income so they establish visa regimes for them. Typically you can stay for 12 months -- as a visitor, your status typically is not any sort of residency and does not confer any rights towards citizenship.

• Anguilla
• Antigua and Barbuda
• Barbados
• Bermuda
• Croatia
• Czechia not official link, seems like the process is very complicated.
• Estonia
• Dubai
• Georgia
• Germany
• Iceland
• Madeira
• Mauritius
• Mexico
• Norway
• Portugal
• Spain unofficial link again

IANAL, but tourists visas the world over tend to not allow you to work, whomever you do the work for. That said, in practice, who's going to check whether you sit in that internet cafe browsing Facebook or your company intranet.

Well. Scratch that. Probably quite a few countries would be able to know whether you do either.

Note that if you were European, you could travel to many other European countries and keep working, legally.

Also, visa specifications for many African countries state what a visa will allow you to do, but often not what it does not allow you to do. For example, I could not confirm that tourist visas for Kenya, Uganda or Tanzania do not allow you to work for a company that's abroad. And, either way, in practice, they will love the 100 USD or so you will have to pay for every 3 month renewal of their tourist visas.

“Tourist” visas generally do not allow anything like this. “Business” visas or other short-stay rules do give you a bit of leeway but in general work is simply not allowed. And spending a long time doing something from within the country (as opposed as attending a meeting to prepare for work executed elsewhere) would usually count as work, even if you clients/employer and bank account are all abroad.

Now, the regulations are usually written with people taking up local employment in mind and that's also what enforcement is usually focused on (and especially on industries like catering, construction, cleaning, or agriculture). Getting a work permit therefore often requires a job offer from a local company, proving that a resident cannot complete the work, etc. So if you want to do it completely above board and even if you were ready to deal with all kinds of paperwork and taxes, it would still not be easy to do.

It's tempting to think that requirement like having a contract with a local employer imply that regular work permits do not apply to your situation but a simple example can show why it isn't so. In many countries, there are “highly skilled migrants” schemes that require a yearly salary above some threshold and/or advertising the job through official channels for some time to prove that no current resident is able to fill it. Obviously, “I don't have the qualifications needed to find a job like that” has never been a valid reason to be allowed to work outside this system.

The fact that the law in some country was not designed to accommodate you and was not written with remote work in mind does not change the definition of work. As long as the relevant regulations do not explicitly exempt nomad workers from some rules, work remains work and the rules pertaining to it fully apply. By default, you must qualify for whatever work permits are currently available and sometimes it just isn't possible. In most cases, I think that what you are proposing would therefore be illegal even if people can and do frequently get away with it.

This started as a comment, but grew too long.

I would be very careful to get an opinion from the tax authorities in the destination country about what "a temporary resident" is .

I have been freelancing in USA, Asia & Europe for (cough!) decades now and have yet to find a country where I was not deemed resident for tax purposes after 93 days. It can be fun when you spend 94 days in 3 different countris & you had better hope that they all have tax treaties (lest you have to pay all 3, and wait while claiming refunds from 2).

Generally, but be careful to ask the tax authorities in each country - before going there, obviously. After 93 days, most countries want to tax me on my worldwide income.

Note that I am not a US citizen, so ymmv, but, please, do check with the relevant tax authorities and find out, as others have recommended, if the visa which gets you to each country permits work.

Note that without a working visa you are likely to face difficulties with things like opening a bank account in some countries. Without that, you will be paying large US bank fees, but you may also have some difficulties with day to day things. Some countries would not give me a 'phone line, or SIM card without a "native" bank account, and in one they would not accept my Visa card at the supermarket.

Be sure to ask on https://expatriates.stackexchange.com/ and be aware that if, for instance, you take your car, you will probably have to change license plates & insurance after a time, maybe driving license too.

There's a whole world of gotcha out there, just waiting for you ;-)

Have you heard of PT? http://en.wikipedia.org/wiki/Perpetual_traveler

Who says you can't work online for your home country while on a 90 days visa free stay in Chile, Brazil, etc?

The whole point concerns tax. AS you already pay tax in your home country and do not stay more that 180 days a year in one country, you are considered not resident for tax purposes. Check expat forum and the laws in each country. In general any country where you can stay visa free less than 6 months is good. An you being an American, you are the only citizen in the world, apart from Eritreans, that pays tax based on nationality, so even if you wanted not to pay US tax, you could only do that by renouncing your US citizenship.

Read more about flag theory.

The whole situation is quite a new one. Today, I can work from home, and I can just as easily work from any country where I get power for my laptop and a decent internet connection. Ten years ago that was just impossible. So it's not surprising that visa rules don't take the situation into account at all. On the other hand, no visa in the world would ask you to give up your job (in another country). If you are a US traveller, no country would think there is anything bad in coming to their country while you are holding a job in the USA.

But let's look at the visa rules. For example, a UK visa says it is for "travelling to the UK for leisure (not work or study)". But you are not travelling to the UK to work. You are travelling to the UK for leisure. The work is something you can do anywhere in the world, so you are not travelling to the UK for work.

I'd read the visa rules for whatever country you want to visit, and decide whether you can reasonably argue that the rules don't disallow you from doing your US job while sitting on a sunny beach, or in a cafe in the middle of Paris, and so on. Between the fact that nobody will notice that you are working, and that you can reasonably argue that you are not violating any visa conditions, you should be fine.

Short Answer of the Legal Gray area in between that needs Juris Prudence:

• In general, Tourist visas do not allow you to work as employed in the issuing country. But, they do not prohibit you from doing your 'home' work while on vacation.

• There are explicit things and implied concerns here and will vary from nation to nation.

Before laws can be created, formulated, articulated, ratified and then be approved by a Nation's legal / govt system there is certain amount of Juris Prudence that has to be undergone to establish ground, premise, case & jurisdiction for how those laws would be established & executed.

Pertinent Question to ask: What Counts as "Working" in a scenario ?

FINANCIAL INTERCHANGE or PAYMENT or TRANSACTION that a NATION or GOVERNMENT finds UNDER THEIR PURVIEW or JURISDICTION and /or their INTERESTS and APPLY LEGAL, FINANCIAL, TAX & Other Ramifications to those said INTERCHANGES.

AND in EXECUTION,

Then its ability to TRACK, DETERMINE APPLICABILITY, ELIGIBILITY or COVERAGE and ENFORCE the above.

PS: E.g. US Citizens are taxed in certain manner irrespective of where they are, but they can't or don't tax them on EVERYTHING, EVERYWHERE.

But, we must first ask what counts as "working" in said Nation "X" under a "tourist visa"?

Typically, a Work Visa (or Legal Work Permit/ Eligibility) or similar Professional/ Business is required if your intent and action entail "work" that has legal/ financial implications in the said Nation.

Basically, its a legal approval or disapproval to engage in "RECEIVING Financial Payment for SPECIFIC ACTIVITY" under the said Govt & Jurisdiction.

So what counts as work?

• For a chef cooking a meal for his friends in destination? But, if he is not being paid for it in a legal/ financial binding as per regulations/ jurisdiction of a country, then is he working from the point of view of that country?

• In an emergency, if a medical doctor on vacation provides some help to someone, without any payment; does it count as work?

• If as an international lawyer, I advise a cousin on how he should tackle something legally, without any fee etc., does it count as work?

• Does a Pilot & Cabin Crew qualify as WORKING in all countries they fly to? They are in fact doing their WORK wherever they go, but are PAID workers only for BUSINESS ENTITIES that EMPLOY them on FINANCIAL basis, on PAYROLL that falls under certain JURISDICTION; mostly a sovereign entity/ nation. In fact, on several international & code sharing flights I've encountered Flight Attendants of same or different airlines working together from Nation A to Nation B while they may be employed or on payroll of completely different BUSINESS ENTITIES of the same Mother Corporation or even totally different ones or contractors / on loan or similar from another agency.

Again, leaving the "medical/ legal practice" privileges aside, these things TYPICALLY do not constitute FINANCIAL / LEGAL WORK ACTIVITY but as PERSONAL ACTIVITY due to LACK of FINANCIAL INCENTIVE or TRANSACTIONS, which would come as being under the purview of "requiring a work permit" from the Nation.

• Now, there are plenty of professionals and entrepreneurs who are jet savvy frequent flyers, hopping between client meetings, conferences/ exhibitions, networking meets etc., while at the same time continuing to "do their work", at times even on vacation.

• So, which part of their "work" should/ could fall under "legally working" v/s "illegally working"? Typically, when an nation gives a Work/ Business Permit, it entails to the individual or entities "legal eligibility / privilege" to earn money; i.e. salary or revenue from "legal entity" IN that Nation or some kind of financial/ legal activity that comes under its jurisdiction/ purview

So, if I operate out of Nation A, my client is in Nation B, and I am passing through Nation C for a week long conference while continuing to work on proposals and projects for my client, am I violating "legal work privileges" of Nation C? If, that would be the case, there are tons of people who are currently working illegally.

Would it even be possible for me to ask Nation C for a "work permit"? They would pretty much say, that does not fall under their purview.

Even if they wanted to the Nation cannot offer any "work permit/ privilege" for the person/ entities work in the said Nation, as that work is out of their financial/ legal jurisdiction.

I believe, Work/ business when outlined in any nation is related to work/ business that falls within the jurisdiction of their legal / financial frameworks - whether local or international.

Work vs Residence Tax?

On the other hand, residency parameters where a person is liable for taxes beyond X number of days is another legal/ financial regulation per se. But, that is related to TAXATION, not legality to do what they do.

Exception being if staying beyond a set period (e.g. 180 days in some places) makes you eligible / liable to pay taxes.. I think the OP was asking in general. For perpetual stay, the laws may be different for all nations & their treaties.. then again, hard to enforce for remote work done on a laptop.

So anyone from the US who is working on their laptop or smartphone for an entity and earning salary/ revenue from an entity that has no legal / financial relationship with the "passing through/ touring through nation" while on short or long vacation is not under any penalty. Why?

Again, as we get into international laws, multinational businesses & corporations who have legal/ financial footprints across national borders, expat assignments & intra-company transfers (employee transfer in an MNC from their department in Nation A to Nation B), this question becomes more complex, and better suited for the "Expat & Legal/ Immigration/ Taxation/ Business" areas.

End Note:

Most people end up doing their work/ personal stuff while traveling as long as no "financial/ legal premise or interchange is established" between said entities/ parties under the JURISDICTION / Legal & Financial Frameworks of the said Nation; as long as your US employment i.e. employer-employee relationship has no direct legal, financial bindings with the destination country of tourism or TRANSIT, you should not come under the said Jurisdiction.