2022 is a good time for wannabe digital nomads. The Covid-related travel restrictions are already relaxed in most countries, while most IT companies still offer flexible work options. Not wanting to miss out (but also not willing to fully commit to the remote lifestyle), I’ve been taking short work-from-anywhere trips this year. Visiting Slovenia 🇸🇮, Italy 🇮🇹, and the Baltic states 🇱🇹🇱🇻🇪🇪, I tried to gently blend fun and work in a safe, time-bounded frame of 1-2 weeks at a time. Here’s how it went!
The good parts
There’s a lot to like in a short term work-from-anywhere trip.
Firstly, you get to break the everyday routine. New place, new views, new sounds. Just waking up in that amusingly unconventional Airbnb in Riga and setting up shop on the kitchen table can feel exciting, or at least refreshing.

Riga 🇱🇻

Tallin 🇪🇪
Secondly, travel is, supposedly, the greatest teacher. Even in today’s world of convenience, point-to-point cheap flights and contactless check-ins, you’re never safe from a sudden exposure to another country’s culture or language. Hell, if you travel alone and you are comfortable talking to strangers, you may even meet someone and make friends along the way!
Then, there’s the lifestyle experimentation benefit 👩🔬 – no need to fantasise about how it would feel like to go nomad and work from the cafés around the world. You can just give it a try for a few weeks and see for yourself! (And then perhaps get back to the more predictable, stationary lifestyle with a sigh of relief.)
Oh, and you get all this without necessarily using any vacation days – shut up and take my money!
The bad parts
Remote work amplifies travel worries. Since no-one makes you go on the trip, it’s you who’s responsible for having good working conditions. If you’re an experienced, stoic and flexible traveller, you’ll likely be fine. If half of your travel memories are those of being infuriated about the little things that tend to go wrong (delays, water outages, wonky Wi-Fi, noisy neighbours, bugs, a group of Icelanders chanting songs at 4 AM in the Great Northern Hotel), you may want to reconsider.
Then, there’s a big flipside to this “enjoy travel without taking vacation days” coin. Because you’re still working, you’ll be spending most of your workdays, well, working! This can in the end make the entire experience disappointing (as in: yes, I just spent 3 days in Trieste, but I spent most of my time on email and meetings).
You can try to compensate for this by packing your breaks and evenings and weekends with exploration, museum visits, runs, pub crawls and walking tours – and it can work, but then you’re risking over-exhausting yourself. (That’s how innocent people end up drinking Latvian Balsam shots in a Riga bar! 😅)
Finally, Socrates said it best: “Why are you surprised that travel does you no good?”. As elegantly explained in this blog post , Travel is no cure for the mind. If what you’re after is some vague quest for meaning or an attempt to distract yourself from anxiety, travel may not be the solution. (Unless you find your meaning in blogging about remote work, which I don’t think ever worked for anyone;)).
After that optimistic note, let’s talk about logistics!
Duration
Everyone will have their own sweet spot for a short-term remote work trip. One advice I’d offer is to plan to spend more days in each place that you’d do on vacation – to account for the time you’ll be working and have more opportunities to explore in your free time. What I ended up liking the most is a ~1 week schedule (extended with the weekends on both ends), split between two destinations.
Hotels or Airbnbs
My first remote work base was a really nice hotel on the edge of a picturesque lake in Slovenia. It had a beautiful view, good Internet and an excellent breakfast. I was pretty sure I was going to love it. I didn’t. Because so many of the basic needs (including breakfast) were provided by the hotel, I ended up spending too much time there, and feeling that I replaced my usual routine with another one, just weirder.
So I took a bus to the capital and tried an apartment rental. This worked so much better – for one thing, apartments are usually bigger than hotel rooms. They also feel more suited for humans to function during the day. Finally, they make you go out and find breakfast the first day in the morning, no escaping from the society!
And so, I ended up strongly preferring apartment rentals.
Gear
The most important piece of gear is the chair, and you’ll most likely not be bringing one with you. Chairs can be characterized by the amount of time you can spend sitting in them in relative comfort. There are 15-minute chairs and there are 4 hour chairs. An attempt to spend the entire day working in a 15-minute chair is a guaranteed path to frustration and back pain.
If you’re staying in an apartment, pay attention to the chairs in the apartment photos. If staying in a hotel, email in advance and ask for an office chair to be placed in your room. Bigger hotels can usually accommodate that, see below the before-and-after in the same hotel room in Slovenia.

Regular hotel room chair.

Office chair the hotel put in the room (free of charge).
To compensate for the increased travel worries, redundancy is your friend. Get a good data plan on your phone as a backup for wonky WiFi. Bring an extra charger (and carry it in a different place than the other one). Pack an Ethernet adapter and cable. And for the occasions when things go wrong regardless… I guess install Headspace on your phone.
Summary
A few trips in, I like work-from-anywhere… in moderate amounts, and not too frequently. If you have a recommended destination, drop a comment below 📝 :) !