The Truth About Workation: What It Means, and What It Actually Takes

A few years ago, in October, my partner and I rented a two-level cottage in the Carpathian mountains. We picked it because it looked quiet, had a view of the hills, and was cheap enough for a full month of stay. Friends came to visit partway through the trip, and so did the neighbors' cows, who wandered by our fence every now and then.

It was our first workation, and, truth be told, it was nice. We worked throughout the day and went for hikes in the afternoons if the schedule allowed. It was not what you usually see in the workation advertisements, where some guy is typing away on his laptop by the pool. It felt more like normal life, just moved to the mountains.

This article is an honest look at what our first month-long workation was really like, from planning and unreliable internet to transport headaches and the small surprises that made the experience worthwhile. If you're wondering whether a workation is actually practical and what it takes to pull one off, this is the guide I wish we'd had.

Workation meaning: what it actually is

Workation means combining work and vacation into one trip: you keep working your normal hours, but you do it from a destination you'd otherwise only visit for a holiday. It's not a day off, and it's not a business trip either. You're still logging into calls and hitting deadlines. You just do it with mountains, a beach, or a new city outside your window instead of your usual office or home desk.

The word itself is a mashup of "work" and "vacation," which tells you most of what you need to know. It's not a loophole that gets you out of working. It's a change of scenery for the same job you already have.

Workation vs vacation: what's the real difference?

A vacation means you stop working. A workation means you keep working, just somewhere else. That difference matters more than it sounds.

On a vacation, your calendar is empty, and your only job is to relax. On a workation, your calendar looks the same as it does at home: meetings, deadlines, emails. The only things that change are the view outside your window and what you do after you log off. If you go into a workation expecting it to feel like a holiday, you'll be disappointed by day two.

Workation vs being a digital nomad: are they the same thing?

They get mixed up a lot, but they're not the same. A digital nomad has no fixed home; moving around is the lifestyle itself. A workation is a temporary trip, and you still have a home and a normal routine waiting for you at the end of it.

You can take a workation without ever becoming a digital nomad. And plenty of digital nomads wouldn't call what they do a "workation" at all, because for them it's just how life works, not a break from it.

Photo by Weavehall Collective

How common is workation?

Workation is actually more common than you'd think, but there's a gap between who wants one and who actually gets one. Only 34% of employees have taken a workation, while 72% say they want to, which means the main thing standing between people and a workation usually isn't desire. It's whether their employer allows it.

The line between work trips and personal trips is also blurring. About 67% of business travelers extended at least one trip for personal time in 2025, up from 43% just a few years earlier. Workations sit on the same spectrum: more people are choosing to combine work and travel rather than keep them separate.

How we planned our first-ever workation

Before this trip, neither of us had ever spent a full month working away from home. We didn't have a car either, so we couldn't simply book the prettiest mountain cabin and figure everything else out later. Every choice had to work with public transport, nearby shops, and the reality of living there for four weeks instead of just a weekend. And we also had to come up with a suitcase hack to fit everything we needed.

Finding the right place took us more than a month

We compared dozens of cottages, trying to balance three things that rarely came together: a price we could afford for an entire month, enough comfort to live and work there every day, and internet that looked reliable enough for video calls.

We ruled out plenty of places because of the WiFi

Internet is not an amenity for a workation but a necessity; it is the factor that determines whether you are able to do any work at all. We reached out to the hosts and asked about the quality of their internet connection and read reviews in search of any mentions of using video chat. This led us to skip some wonderful cottages that had everything except a reliable internet connection.

We also knew about the problems with mountain internet connectivity, so we decided to plan for a mobile data alternative, which proved to be easy since we were traveling in our own country.

Getting there was part of the adventure

The planning for the trip took nearly as much time as planning our place of residence itself. We traveled by train, then by regional bus, and then by local taxi shuttle, which would take us to the village where we booked our place. The most difficult thing was not to plan the schedule, but the transportation for the last few kilometers of our journey. It turned out that communicating with local taxis can be quite problematic, and it made us realize that remote destinations take much more planning than it seems at first glance.

It is now clear that all this planning paid off. Moreover, it showed us that the process of organizing a workation starts far before opening our laptops.

Expect the unexpected on a workation: the day the storm cut everything off

One morning, somewhere in the middle of our stay, a storm rolled through and knocked out both the internet and the electricity in our area. We didn't have a generator or another way to get online, so all we could do was wait for the local crew to restore the service. It took most of the day.

Outage wasn’t the most problematic aspect. Uncertainty is what made us uneasy. We had no clue how soon we would get our Internet connection back – in an hour’s time or maybe in the morning? When one’s work depends on having Internet access, uncertainty causes stress.

It's a good reminder that even with careful planning, things outside your control can still happen. 

A workation doesn't remove the everyday challenges of remote work. Sometimes it adds a few new ones. Power cuts, unstable internet, bad weather, or transport disruptions are all more likely in remote locations.

Another surprise: I changed my job

The workation turned into something much bigger than a month in the mountains. During that time, I interviewed for a new role, accepted an offer, and quit my old job.

It's one of my favorite memories from that trip because it completely contradicted the stereotype that a workation is just a long holiday with a laptop. I was working full-time, planning my next career move, and thinking about starting a freelance business (maybe a blog?), all while mountain trails waited outside after work.

Helpful workation tips: what actually makes it work

If you're planning your own workation, a few basic things will save you a lot of stress.

1. Check the internet before you book

Inquire directly from the host regarding the internet speed and whether blackouts are common in the area. In case your work cannot afford to lose an afternoon, have a backup plan, such as a nearby café or coworking space with its own connection.

2. Respect your work time as you would at home

Block them off the same way you would at home, and save the hiking, the exploring, and the wine for after you log off. Mixing the two during work hours is how deadlines get missed.

3. Pick a stay long enough to settle in

A week is too short to get into a groove. Several weeks give you time to acclimate, meet new people, and actually enjoy where you are rather than just being a transit point.

4. Consider a destination built for it

Popular workation spots like Portugal, Bali, or the Canary Islands are popular for a reason: reliable wifi, coworking spaces, and a community of other people doing the same thing. If you're headed somewhere quieter, like a mountain cottage, you'll need to do more of that planning yourself.

If you'd rather hike than sit in a coworking space, mountain regions like the Carpathians, the Alps, or the Pyrenees can work just as well for a workation. You'll trade some convenience for it: fewer cafés with wifi, less of a built-in remote work community, and a higher chance of the odd lost afternoon. For many hikers, that trade is worth it.

5. Think beyond the accommodation

Your plans will not just end after finding a good accommodation. Make sure you know how you will get to your chosen destination, where you can buy groceries, whether public transportation is available, and what you will do if you decide to return early. We were not prepared for how much effort we had to put into these logistical tasks, especially since we didn’t have a car. A workation is much more enjoyable when the practical side of daily life is as well planned as your workspace.

How to ask your employer for a workation

Since demand for workations is well ahead of how many companies actually allow them, getting a yes often comes down to how you ask. Check whether your company already has a remote work or workation policy before you bring it up; some do and just don't advertise it.

Come with a plan. Say how long you'd be gone, how you'll stay reachable during your normal hours, and what you'll do if you lose power or internet for a day, since that's the question most managers will actually worry about.

Is workation worth it?

For us, yes. Being far from home was scary at first, but we never regretted this decision. We got a change of scenery, hikes we wouldn't otherwise have taken, and I even walked away with a better job by the end of it. The storm was a bad day, not a bad month.

Go ahead if you feel like giving it a try, but do not think of it as a vacation without any responsibilities. Do not just consider where you will be working from, but also the internet, travel arrangements, and the usual activities you will do aside from work. Get those right, and you'll have a much better chance of enjoying both your workday and everything that comes after it.