The rise of the workation: the new remote work travel trend

The rise of the workation: the new remote work travel trend
A banner for a workation in Dubrovnik picturing Old Town Dubrovnik

When you can work from anywhere, where will you go?

Location-independent or 'remote' work began as a niche subculture in the startup and freelancer world in the 2010s, was accelerated by the pandemic, and is now an unstoppable trend (despite the efforts of governments to reverse it).

What is a workation?

The term 'workation' is a portmanteau of 'work' and 'vacation'. It describes an emerging genre of travel that marries two common concepts (being at work, and being on vacation) that have traditionally been very separate.

What does it mean to go on a workation? Well, vacations are essentially formal breaks from work. That's the point.

'Vacation time' is a benefit provided by companies and enshrined in labor laws that allows for employees to take time off from work responsibilities for several weeks a year, while still retaining their salary.

Often, people use this time to go on trips to destinations that interest them. The rhythm of life is mostly workweeks — and every once in a while the predictable beat is interrupted by "vacations" where people turn on the out-of-office autoresponder, and head out somewhere fun. People look forward to vacations. They plan them. They reminisce about them. They wish they had more money or time to do more of them. They count down the days to "being on vacation".

Yes — Vacations are wonderful, but for remote workers whose employers don't care where they do their job from and can legally choose from dozens of countries to work in, new freedoms break down old ways of thinking.

The simplest definition of a workation is this: temporarily relocating to a desirable destination, without interrupting your work commitments.

For example, a project manager who lives in Minneapolis and works for a remote-friendly London-based company could find an AirBnB in Dubrovnik, obtain a remote work visa from the Croatian government, get on a plane on Saturday, and be sipping cappuccinos on the Mediterranean on Sunday.

Here's the interesting part — on Monday morning, she can simply open her laptop on their balcony, or in a local coworking space — and begin a normal full-time workday.

In the evenings and on the weekends, instead of going through her normal routine, she can explore historic medieval cities or take day trips to nearby islands and destinations.

Many remote workationers might even find that there are global destinations that bring a welcome change of pace — but also a cheaper cost of living.

In that sense — with the combination of continuing to work full time, living normally (i.e. not "splurging" in the way you think of on a traditional vacation), and finding places in the world that may actually have a lower cost of living—workations may not present as big a burden on the bank account as traditional vacations do.

Workation-seekers create a new category of traveler, distinct from the typical tourist or backpacker.

An overview of different types of travelers
Workation-seekers are a different category of traveler from tourists and backpackers.

Remote work and digital nomads

We've talked about workations using an example of an employed worker who has the freedom (permission from their employer, and a legal visa from a destination country) to work remotely. But remote work is also a very popular concept with entrepreneurs, freelancers and digital nomads.

Digital nomads, business owners, entrepreneurs and workers may even let go of the traditional concept of "home" and choose to perpetually travel. For tax and citizenship purposes, they will likely still have some country that remains their tax residence — but in practice they will experience their working life as almost a series of 'workations', travelling to one area for a short-term or long-term stay and then moving on.

Digital nomads and remote workers were among the early adopters who have driven the first wave of workations globally.

Why would someone go on a workation?

There are benefits to staying in a particular location, investing time into your community, and growing tight, local bonds with family, friends and neighbours where you live. This is how most people choose to live!

But let's be honest — even if most people don't necessarily want to head off and work around the world for a full year, many would admit that there are dream destinations they would visit for a few weeks or a few months, if the stars aligned.

Here are some reasons people would go on a workation:

  • A change of scenery can help you learn about the world, feel inspired, meet new people and make new friends (and lovers 😘)
  • When your work-life routine can seem like one big hamster wheel, a workation can help you evaluate what matters most to you, by giving you new perspectives without sacrificing the safety and continuity of how you earn your income
  • Workations allow you to pursue and try hobbies, cultural experiences and adventures that may not be available near where you live
  • Workations help you visit places that you think will make you healthier and happier (even if just in small doses). For many, working from, for instance, Costa Rica might be perfect for two months of healthy eating and exercise, but absolutely not the ideal place to live full-time
  • Workations allow you to find your rhythm of being a 'snowbird' and chasing the seasonal weather you desire — without even being retired!
  • Workations can help you avoid impulsively quitting a career that you think is burning you out — maybe it was just your daily routine, not the 'job'? Workations allow you to find out...
  • If you are a businessperson, salesperson or someone whose livelihood benefits from making in-person connections, workations allow you to relocate to places where you can build and strengthen valuable contacts more meaningfully than on short 'business trips'

Workations will reshape destination marketing strategies

From May 5th to 7th, 2022 a small group of attendees gathered in Dubrovnik, Croatia for the conference.

The event, supported by local government and digital nomad community builders like Saltwater Nomads, was conducted to promote Croatia and Dubrovnik as a destination for digital nomads (and remote employers), and educate attendees on issues that can help facilitate remote work — including attendees representing other digital nomad destinations like Scotland, Venice and Albania.

This conference and its agenda are an example of a new kind of marketing conversation emerging as destinations compete to market themselves to remote workers. Cities will now find themselves needing to rethink the 'tourism marketing' playbook for attracting digital nomads and remote workers. Remote workers don't value all the same things that tourists and backpackers are looking for.

Cities and countries will pass legislation, adjust advertising campaigns, shuffle marketing budgets and develop public-private partnerships that aim to attract remote work workation-goers, who stay in town longer than tourists, spend more, contribute more to the economy, and possibly even start down the path to relocating and investing in their future.

At the municipal, regional and national level, places will compete to become 'workation destinations of choice'.

And short-term rentals, hotels, and accommodations will adapt to become more supportive of longer term workations. Vacation accommodations without high-speed wi-fi and a comfortable place to sit and work will not be the accommodations of choice for remote workers and digital nomads who need to be productive while they travel.

Oh... and have you heard of Starlink? When Elon Musk's vision to beam the Internet down from the sky takes off, even more remote locations can become viable workation hotspots.

Workations will drive markets for support services: tax planning, visa consulting, travel insurance and "package workations"

As we learned by attending Running Remote 2022 in Montreal this year, there is a growing list of vendors whose primary focus is supporting remote workers and remote-focused employers.

People who want to go on workations have legitimate questions about how to achieve their plans. They will ask themselves things like:

  • What do I do about taxes if I am a resident somewhere else?
  • Do I need a special visa to legally work somewhere else for a week, a month or a year?
  • What kind of health insurance will I need when I am staying and working abroad for an extended period of time?
  • What if I don't want to do this alone — how will I connect with other like-minded people so I can have fun, make friends and make new connections?
  • How will I know where to go and what to do? How will I maximize my precious time in a destination while on a month-long workation?

Look out for workations to be a hot market, possibly under a variety of other names like "remote work retreats", "digital nomad excursions" and more.

When people can work anywhere, the future of travel is bound to change... dramatically.