For those lucky enough not to be tied to an office – or even a country – working while travelling around the world is a real and exciting option.

It’s not advised to work remotely overseas without informing your boss, but if you get permission, one of the hardest parts of the process can be choosing where to go.

To that end, Remote, a global payroll, tax and HR platform, has put together a list of the top 100 areas for remote workers.

Spain’s capital Madrid scored the top spot, with Remote praising its “perfect combination” of classical art, architecture, cuisine and “ideal conditions” for remote workers visiting the country.

“No matter how long you’re looking to stay, Madrid is ever welcoming, thanks to low taxes and generous expat visa options targeted at freelancers and remote workers,” Remote said.

Portugal’s Madeira region ranked second, thanks to its “competitive tax rates, generous residency options, co-working and living spaces … and a burgeoning start-up community”.

Toronto, Canada rounded out the top three, noted as one of the world’s “most welcoming” cities for international transplants who can largely expect safety, good quality of life and things to do.

Remote said it based its rankings on aspects including:

• Internet infrastructure
• Attractiveness (cultural, urban, natural or other)
• Societal openness
• Quality of life
• Incentives for remote workers
• Cost of living
• Inflation

Solitary Australian entry on list

Australia’s only entry on the top 100 list was Sydney at No.17 – despite reaching No.10 in a previous edition of Remote’s report.

Sydney ranked extremely well in openness, quality of life, attractiveness and safety.

It fell short on internet infrastructure and cost of living, which is unlikely to surprise locals.

Centre for Future Work industrial and social policy director Dr Fiona Macdonald told The New Daily some of Australia’s smaller state capital cities would likely work better than Sydney for remote workers as the cost of living – particularly housing – is so high.

But she said with Sydney being a major international visitor drawcard, those looking to only spend a short period of time working remotely in Australia – or those with money to burn – are likely to continue to flock to the city.

Expert tips

For remote workers looking to move internationally, Macdonald said they should keep in mind aspects such as internet connectivity; timezone compatibility with your employer; housing affordability; work rights and availability of digital nomad visas; tax, social security, and income implications; and opportunities for social connections.

“Whether or not it’s going to work for you income wise would depend on what you’re earning here [in Australia], where you’re going to, and expenses there,” she said.

“Also [your destination’s] tax and social security arrangements for foreign workers, which will vary with … the digital nomad visas that they have.

“Some countries have particular tax incentives that wouldn’t normally have existed for foreign workers … there are lots of conditions around those visas.”

Griffith Institute for Tourism professor in air transport and tourism management Gui Lohmann said he was surprised most of the entries on Remote’s list were so central, given the recent shift away from cities by many workers seeking lower cost of living and better work-life balance.

For example, cities such as Tokyo, Paris, New York and Sydney, which all ranked high on the list, are very expensive to live in.

Lohmann said Madrid and Madeira made more sense, as did other cities included in Remote’s list such as Thailand’s Bangkok (No.16), America’s Concord (No.23) and Malaysia’s Kuala Lumpur (No.22).

“There are a lot of interesting smaller and medium centres that definitely attract workers who will be then spending money in their economy,” he said.

“But the simple fact that many, many countries are offering [digital nomad] types of visas, it’s a clear sign that is a benefit for … particularly smaller countries in the periphery regions [such as] Georgia, Croatia and Estonia.”

The continued blending of business and leisure – sometimes referred to as ‘bleisure’ – is a sign of an increasingly fluid society that’s becoming less rigid when and where people are working, Lohmann said.

And Australia needs to keep its foot on the accelerator, particularly by improving local internet performance.

“It will be great if Australia could force this beyond our larger capital cities, particularly in terms of infrastructure development,” he said.