Workation Wandering: Your Ultimate Guide to Balancing Work and Travel

Dreaming of trading spreadsheets for sandy beaches? Workations might be your answer! But before you book that exotic Airbnb, let’s clear the air with some quick Q&A’s:


What is a workation?

Think business trip meets vacation! A workation blends remote work with leisure in a new location, from a few days to months at a time.


How do companies offer workations?

Policies vary depending on the industry and your company culture.  Some industries (like banking) have a conservative risk appetite and are heavily regulated, so typically don’t offer much flexibility.  Others such as technology companies, so go further. Some offer team retreats, individual perks, or flexible remote work options. We covered the different types of workation policies offered by companies here.


How long can I request a workation?

Depends on your company policy and workload. If you’re an independent contractor you’ve got more flexibility, but if you’re an employee we see companies typically tend to offer between 14-30 days work from anywhere (although some go as far as 90 days, beyond this and the compliance risks tend to be too much).  Whatever you do, make sure to request permission in advance as not doing so can land both you and your company in a lot of trouble.


Which industries offer more workation flexibility?

Tech, marketing, freelance gigs often lead the pack. Look for companies with remote-friendly cultures!


What are the key workation risks?

Other than compliance risks, the other key workation risks include unreliable internet, timezone mishaps, and blurred work-life balance. Plan, communicate, and set boundaries!


What should I worry about with a workation?

Logistics! Secure reliable internet, comfortable workspace, and understand legal aspects in your chosen location.


How can I convince my boss to say yes?

Highlight the benefits, such as increased employee satisfaction, productivity, and the potential for attracting top talent. Present a well-structured proposal showcasing the positive impact on both work and team dynamics.  Also show them that other companies in your industry are already offering this benefit, if they don’t have it in place already.  You can see our blog post here to get some ideas.


What are the tax risks of a workation?

For the Employe: Potential double taxation, reporting foreign income.

For the employer: Establishing a “permanent establishment” abroad (see here for more), triggering tax obligations. 


How do I research tax and legal risks of going on workation?

Talk to your company’s HR, legal, tax and/or global mobility teams. Research local tax laws and consult an expert if needed. Beware of the 183 day rule, as that doesn’t necessarily take away mandatory payroll obligations for the employer. Stay informed on visa and work permit requirements as these are often the responsibility of the employee. And if you still have questions, try out the Work From Anywhere platform to get a snapshot of your tax and legal risks in under 60 seconds.


How can I convince the global HR team to offer workations?

Showcase success stories from other companies (see here for our deep dive on Spotify for example). Highlight benefits like talent retention, productivity gains, and positive employee experience. Prepare a well-researched proposal addressing legal and policy considerations.  You can access our guide for HR directors here.


What are the best workation destinations?

Depends on your needs! Consider time zone alignment, reliable internet, cost of living, and visa requirements. Research digital nomad communities and co-working spaces for inspiration.  Nomadlist is a good place to start, but you can also see other places we covered here


Who are the workation influencers to follow?

We covered many of the key workation influencers here


How Do I Help My Company Implement A Workation Policy?

Whether you’re an employee yearning for more workation flexibility or a senior leader in your organization looking to explore a key employee benefit, we can help.

You can access our free work from anywhere policy builder here, or access a free 7 day trial of our work from anywhere compliance platform here to help your company safely approve workations.  

If you’d like to speak to one of the team, feel free to contact us here and we’d be happy to arrange a demo or see how we can help.


What is a Workation?

Definition of a Workation A workation in the context of remote work is exactly what it sounds like: a blend of work and vacation. It

Read More