Let’s get one thing straight right out of the gate. The whole “workcation” fantasy they sell you on Instagram—the one with the serene-looking person tapping away on a laptop while their toes are buried in pristine white sand, a coconut with a straw in it sweating condensation beside them—is a complete and utter lie. A fabrication. A beautiful, tempting, soul-crushing myth.
I tried it once. The glare on the screen was blinding, sand got into my keyboard (a moment of pure, unadulterated panic), and the Wi-Fi was, to put it charitably, whimsical. My grand vision of firing off brilliant emails between dips in the turquoise water devolved into a sweaty, stressful hunt for a café with a decent connection and an outlet that wasn’t already claimed by another digital nomad nursing a single espresso for three hours.
But here’s the thing. It doesn’t have to be. The concept itself isn’t the problem; the execution is. The idea of breaking out of your soul-crushing routine, of seeing a new corner of the world without torching all your vacation days, is not just appealing—it’s one of the few genuinely revolutionary perks to come out of the whole remote work upheaval. We just have to be brutally honest about what it is and what it isn’t.
A workcation is not a vacation. And it’s not just working from a different, more scenic office. It’s a weird, delicate hybrid. A tightrope walk between productivity and presence. Get the balance wrong, and you end up doing a mediocre job of both, feeling guilty and resentful as you answer emails during what should have been a glorious sunset.
Get it right, though? Oh, when you get it right, it’s sublime. It’s a cheat code for life.
The Art of Not Messing It Up: Setting the Stage
Before you even think about booking a flight, you need to have a come-to-Jesus meeting with yourself. This is the most critical part, and the one everyone skips because it’s not as fun as browsing Airbnb for cabins with hot tubs.
What are you actually trying to accomplish?
Are you on a tight deadline, needing to churn out a massive volume of focused work? If so, a bustling city with endless distractions is probably a terrible, horrible, no-good, very-bad idea. You might think the vibrant energy of Tokyo or Rome will inspire you, but in reality, you’ll just be agonizing over the fact that you’re stuck inside wrestling with a spreadsheet while the entire world is outside having fun without you. For deep work, you need isolation. Think a quiet cottage, a sleepy mountain town, somewhere the biggest distraction is a deer wandering past your window.
Or is the goal to maintain your normal workload while simply changing the scenery? This is a more flexible scenario. You can handle a bit more life happening around you. A small European city, maybe? A place where you can work a solid eight hours and then immediately step out into a completely different culture, grab an incredible dinner, and wander streets that are hundreds of years old. This is about integration, not isolation.
The single biggest mistake is mismatching the destination to the work. We let our vacation brain pick the spot, and then we expect our work brain to just fall in line. It doesn’t work that way. The work brain is a stubborn, petulant child; it needs to be accommodated.
And for God’s sake, be realistic about the “work” part. You are not going to be 120% productive. It’s just not going to happen. There’s a cognitive load that comes with being in a new place—figuring out the currency, navigating the grocery store, trying to order coffee in a language you don’t speak. All that stuff eats up mental bandwidth. A recent Gallup analysis touched on this, noting how engagement and well-being are tied to this kind of flexibility, but it comes with the hidden cost of managing that flexibility. If you normally operate at 100% in your home office, aim for a solid 75-80% on a workcation. Build that buffer into your deadlines and your expectations. If you don’t, you’re just setting yourself up for a spectacular flameout.
The Tyranny of Time: Your Schedule is Your Savior
Okay, so you’ve picked the right kind of place for the right kind of work. Now comes the part where you have to be your own boss. And not the cool, laid-back boss, but the strict, slightly scary one who cares about structure.
You have to compartmentalize. Brutally.
This isn’t about “work-life balance.” That’s a flimsy concept at the best of times. On a workcation, it’s impossible. This is about work-life separation. You need to build a wall between the two, and that wall is your schedule.
Here are a few models I’ve seen work:
- The Sprinter: You front-load your week. You work like a maniac Monday through Wednesday—long, focused hours. You decline the invitations to go explore. You eat at your desk. It’s miserable. But then, come Thursday, you’re done. Or mostly done. You have a glorious four-day weekend to be a pure, unadulterated tourist. This is great for people who have a hard time switching off. It creates a very clear finish line.
- The Split-Shifter: This is my personal favorite. You get up with the sun. You work a super-focused four or five-hour block while the world is still quiet. No emails, no meetings, just pure, deep work. By lunchtime, you’re done for the day. You close the laptop and you do not—I repeat, do not—open it again. The entire afternoon and evening are yours. You go hiking, you visit a museum, you lie on the beach. Then, the next morning, you do it all again. It feels like you’re living a double life, in the best possible way.
- The Minimalist: You only commit to the absolute bare minimum of work required to keep things moving. Two or three critical hours a day. This is less a “workcation” and more a “vacation where you check in a little.” It’s ideal for people who aren’t on a project-based deadline but need to stay on top of communications. The danger here is that those two hours can easily bleed into three, then four, as “just one more thing” pops up. You need iron-willed discipline for this one.
Whichever you choose, write it down. Put it in your calendar. Tell your colleagues. “I am online from 9 am to 1 pm local time, and then I am unreachable.” Setting those expectations isn’t just for them; it’s for you. It’s a promise you make to yourself that the “cation” part of the equation is just as important as the “work” part.
Tools of the Trade (and Sanity)
You wouldn’t go on a camping trip without a tent. Don’t go on a workcation without the right gear. And I’m not just talking about your laptop.
- The Connectivity Question: Before you book anything, you need to become an obsessive-compulsive Wi-Fi detective. Don’t just trust the Airbnb listing that says “Wi-Fi.” That could mean anything. Read the reviews. Search for the word “Wi-Fi,” “internet,” “connection.” If people are complaining, believe them. If you can, ask the host to run a speed test and send you a screenshot. Seriously. It feels awkward, but it’s better than arriving and discovering the internet is powered by a single, exhausted hamster on a wheel. Have backups. A personal hotspot. A plan to use your phone’s data. Know where the nearest co-working space or library is. A lack of reliable internet is the number one killer of workcation dreams.
- The Ergonomics of It All: Look, I get it. Nobody wants to pack an entire office setup. But working for two weeks hunched over a coffee table is a recipe for a back spasm that will ruin your entire trip. A lightweight, portable laptop stand is non-negotiable. It folds up to nothing and it will save your neck and shoulders. A travel-sized keyboard and mouse are also game-changers. Your body will thank you. You’re trying to escape the pains of the office, not create new, more exotic ones.
- The Noise-Canceling Bubble: You cannot control your environment. The apartment you rented might be right above a bar that really, really loves karaoke. The charming café might be charming, but it’s also loud. A good pair of noise-canceling headphones are not a luxury; they are a survival tool. They are your portable cone of silence, your on-demand deep-work zone.
I remember one trip to Lisbon. My apartment had a gorgeous view of the city, but it was also directly above a tram line. A beautiful, historic, incredibly loud tram line that ran every ten minutes. Without my headphones, I would have gotten zero work done. Or committed a felony. Probably both.
The Psychological Minefield
This is the squishy stuff, the part that’s harder to pack in a suitcase. The mental game of the workcation is where most people falter.
You’re going to feel FOMO (Fear Of Missing Out). It’s inevitable. Your travel companions, if you have them, will be heading out for a day of adventure while you have to log in for a quarterly review meeting. It sucks. You have to make peace with it ahead of time. You have to remember the deal you made with yourself: this isn’t a pure vacation. The work is what makes the whole thing possible. The work is buying you this experience.
You also have to fight the guilt. The guilt of not working when you feel you “should” be. The guilt of not exploring when you’re working. It can feel like you’re constantly in the wrong place, doing the wrong thing. This is where that rigid schedule comes in again. When it’s work time, you work. You are a professional. When it’s play time, you play. You are a tourist. You have to give yourself permission to fully inhabit each role when it’s their turn. As Buffer’s 2024 State of Remote Work report highlights, the biggest struggle for remote workers is often unplugging. This struggle is magnified tenfold when “unplugging” means stepping out into a beautiful new city.
And maybe, just maybe, you need to be a little bit anti-social. It’s okay to tell your friends or family, “I love you, but for the next four hours, I need you to pretend I don’t exist.” It’s okay to close the door. It’s okay to prioritize that deadline over a spontaneous trip to the local market. You can go to the market tomorrow. You can’t always push the deadline.
It’s a constant negotiation. A balancing act. But isn’t that what most of adult life is, anyway? The workcation is just a microcosm of the larger challenge: how to build a life that is productive and meaningful, but also joyful and full of new experiences. It’s not easy. It takes practice. My first few attempts were messy failures. But I learned. I figured out my rhythm. I figured out that I need a separate workspace, even if it’s just a specific corner of a tiny room. I figured out that I need that split-shift schedule to feel like I’m getting the best of both worlds.
And now? I wouldn’t trade it for anything. The feeling of closing my laptop in a small town in the Italian countryside, the day’s work done, and knowing that a plate of fresh pasta and a glass of local wine are just a short walk away… well, that’s a feeling that makes all the planning, all the stress, and all the sand in the keyboard worth it. One hundred percent.