How to Work Remotely While Traveling: A Real-Life Guide From the Road

remote work

Feb 18

Written By Kelly W

Working remotely while traveling sounds glamorous, and it can be incredibly rewarding, especially when your office changes every few weeks and your evenings are spent exploring new towns. But what we’ve found makes the biggest difference is planning for the unglamorous parts, like internet reliability, work routines, and energy management.

Jonathan and I have worked full-time from the road since 2019. We’ve done it during a full year on the road, a 3.5-month Colorado & Utah road trip, and a 5-month loop through Ontario and New England. We’ve worked from tiny cabins, hotel rooms, short-term rentals, kitchen tables, backyard patios, and plenty of coffee shops.

If you’re thinking about working remotely while traveling, here’s what that has looked like for us and how to set yourself up for a successful season working from the road.

Table of Contents

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Build Your Work Setup Before You Leave Home

The biggest lesson we learned early on is that your work setup matters more than you think.

It’s tempting to assume you’ll figure it out once you’re already on the road. We did too, but trying to piece together a comfortable workday from hotel desks, kitchen counters, and random chairs gets old fast.

Before you leave, it helps to take a little time to make sure you can actually work a full day with what you’re bringing… not just in theory, but in real life.

Set everything up at home and work a few normal days exactly how you would while traveling.

You’ll start to notice what’s missing, what feels awkward, and what you don’t actually use. That small bit of prep has saved us so many frustrating mornings in unfamiliar places, and it makes settling into each new stop feel calmer and more familiar.

Here are our non-negotiables for remote work:

A reliable laptop + backup chargers
Noise-canceling headphones
External mouse and keyboard
Portable monitor(s)
Foldable standing desk
Docking station
Blue-light glasses
One dedicated tech organizer (or computer bag) so nothing gets lost

2. Plan Ahead For Time Off

One thing that makes working trips feel good instead of exhausting is deciding on time off early, before you book the whole route.

When we’re planning a trip, we usually start by asking ourselves a few simple questions: how long do we want to stay in each place, how much exploring sounds realistic after work, and what a normal workweek needs to look like while we’re there. Those answers shape everything else, including whether we need to request time off or whether evenings and weekends will be enough.

In general, the longer we stay somewhere, the less time off we take.

Three-week stays (or longer) usually feel pretty sustainable without PTO because we have plenty of evenings and weekends to explore, and the slower pace makes it easier to settle into a rhythm.

With one- to two-week stays, we’re more likely to take a day or two off so we can see the highlights without trying to cram everything into a couple of evenings.

If we’re only somewhere for a weekend, we almost always take at least a day off, especially if we’re also fitting in a long drive to get there or to the next stop.

That’s also why we plan our road trips from “big picture” to “small details.” We map out the general region and the overall length of the trip first, then fill in the individual stops and decide where time off will make the biggest difference.

For example, while roadtripping across Colorado and Utah, we planned the full three and a half months first and then built in everything from quick city weekends to longer bases like a month in Kanab. Once the route was mapped, it became much easier to see which stops needed extra breathing room and which ones didn’t.

If you’re planning your own version of this, it helps to think through three things:

Where you’re headed and for how long
How much daylight you’ll actually have after work (summer makes this easier)
What feels most important to experience in each place

From there, requesting time off becomes less of a guessing game and more of a simple decision, and you’re far less likely to leave somewhere feeling like you barely saw it.

Internet Is the One Thing You Can’t Fully Control (So Have a Backup Plan)

Internet is the wildcard of working from the road.

Most of the time, you won’t know exactly how reliable it is until you arrive. Reading reviews has been the best way for us to get a sense of what to expect. We usually search for words like “wifi,” “internet,” or “work” to see what other travelers mention on sites like Airbnb or VRBO.

Over several years of working remotely, we’ve only had one short-term rental that advertised much better internet than it actually had. But when it happens, it’s stressful, especially if you’re on calls or relying on stable connections.

Because of that, we always like to have a backup plan. Sometimes that’s hotspot access on a phone. Sometimes it’s knowing where the nearest coffee shop, library, or coworking space is, just in case.

Thinking through internet backups ahead of time takes a little pressure off and makes it easier to roll with small surprises when they come up.

Creating an On-the-Road Office Helps You Settle In

When we’re choosing a place to stay, we almost always think about where we’ll be working.

Most of the time, we work from our hotel or short-term rental, so we look for spaces that clearly show a desk, table, or area where we could work comfortably for a full day. An actual desk is ideal, but a larger kitchen table or island works well too. Because I travel with a portable standing desk, I’m also okay working from a kitchen island/countertop.

Once we arrive, one of the first things we do is set up our workstations and try to leave them set up for the duration of the stay. Having a stable place to work helps each stop feel more familiar, even when everything else is new.

We’re also open to having secondary work spots when it makes sense. When the weather is nice, we love working from outside tables or patios for part of the day. But having a reliable indoor setup always comes first. That balance makes it easier to enjoy the views without sacrificing focus.

As you look for lodging, don’t forget to look for a place to work. It should support the same setup you tested at home, whether you plan to walk to a nearby coffee shop, library, or coworking space, or to work from your hotel (which may also have a business center) or a short-term rental.

View from the kitchen table during our two-month stay in Bryson City, NC. We both worked full-time from a large dining room table.

During our one-month stay in Winter Park, CO, we mostly worked together at a large kitchen island. However, when we were both on calls at the same time, one of us would work from this small sunroom.

When the weather is nice, we love working from outside tables or seating areas. This was my secondary office for three weeks in Ellsworth, ME. (A desk inside our short-term rental provided my main working area while Jon worked at the kitchen table.)

Keep a Road Routine for Sustainability

We’ve found that keeping our work schedules fairly consistent helps everything feel more manageable. We set a regular work schedule and stick to it as much as possible, just like we would at home.

Jonathan usually works Central hours, since we spend part of the year in Texas. I tend to work local hours. Occasionally, we’ll shift earlier if we want more daylight after work, especially during shorter days.

Having a familiar routine makes it easier to stay focused, avoid distractions, and balance work and travel on the road.

It doesn’t need to be rigid. Just familiar enough to give your days some shape so you can settle in for a longer period of time.

Embrace the “Weekend Warrior” Mindset

Unless you’re taking extended time off, a lot of your exploring will naturally happen on evenings and weekends. That’s just part of working from the road.

Embracing the weekend warrior mindset means there will be weeks when it feels busy, especially when you’re balancing a full-time job with the excitement of being somewhere new. That busyness can be tiring, but it’s also part of what makes this season memorable.

Some of our favorite moments haven’t been big sightseeing days. They’ve been morning walks through local parks, finding a coffee shop we keep returning to, or going back to the same dinner spot because it started to feel familiar.

Working from the road has a way of making you feel like you’re living in places, not just passing through them. It’s one of the best parts of working remotely while traveling.

Just like you would at home, you’ll learn over time when you need rest days on the road. Days where you stay in, do laundry, watch Netflix, or just move slowly around town. Those days matter too.

Working and traveling at the same time is a lot. Letting yourself move at a human pace makes it more sustainable and, honestly, a lot more enjoyable.

Yes, you’re going to try to cram a lot of sightseeing into your evenings and weekends, but that’s because there’s a lot you want to do. So the busyness is good, even if sometimes it feels overwhelming. And when you do get tired on the road, remember: that’s kind of the whole point. You’re working and traveling full-time, so soak it up as best you can. It might be cliché, but these are the good old days!

Keep Reading

12 Things to Know for Working From The Road

11 Truths About Traveling While Working

8 Packing Tips (+List) for Digital Nomads who Work From Anywhere

How to Keep Devices Charged on a Road Trip

How to Get WiFi on a Road Trip