The opportunities for combining travel and work have never been so clear. But despite more companies and freelancers embracing the possibilities, this style of working (and traveling) isn’t without its challenges.

I’ve been working online since 2012 (yep, when this was still a novelty!) and I’ve learned a thing or two over the years.

Here’s a complete guide on how to work remotely and travel.

Benefits of remote work trips

The obvious benefit is that you get to spend some time in a different location while still earning your income as usual.

It’s a chance to get away from your typical routine and to see the world without having to give up your career.

You can spend the day working from wherever there is WiFi, then spend your evenings and weekends in nature, surfing, or chilling in a hammock. (Like me here, on the Canary Islands…)

You can choose to become a full digital nomad, but smaller remote trips offer many advantages as well.

Combining some remote working with a regular holiday can make your holiday easier to plan. You actually get some time to acclimatize and work for a while before touring the destination. You can fly in- and out at your own schedule, avoiding peak times for tourism such as Easter or Christmas.

It can also give you new possibilities for spending time with loved ones abroad, avoiding dreaded commutes, and properly pursuing hobbies (at last… you can go kite-surfing every day).

And, of course, working remotely may allow you simply to travel more. However, the style of travel will clearly be quite different than when you are travelling only for fun. 

How to start working remotely

Don’t miss these other essential resources: 

Do you want to know how to find remote jobs, apply successfully, and nail the interview process and negotiation? Then enroll in the Go Remote Employment Course. Use the code “indietraveller” for 50% off!

Challenges of remote work and travel

The level of freedom you can experience is clearly amazing, but it does come with its own set of difficulties.

Here are a few to keep in mind:

If you don’t work for yourself, the biggest and earliest hurdle is the dreaded approval from your employer. Your boss (and/or your clients) need to be on board with the idea. Or you need to find another way to work remotely. 

Working remotely while traveling often requires self-discipline and motivation. It can be hard to focus on work when you’re in an exciting destination that they’re itching to explore! Potential distractions and FOMO are all around you.

The desire to explore every corner of a new destination can interfere with your productivity… and you can find yourself having some very un-fun late-night cramming sessions just to meet a deadline.

Besides practical issues such as travel costs and ensuring stable and reliable internet, there are also various legal, tax, and technical implications to working remotely abroad. 

So let’s look at how to make the nomad lifestyle best work for you — whether you’re planning a short remote work trip or dreaming of going around the world with a laptop under your arm.

Tips for working from anywhere

1. Check if your employer allows it

This is where tiptoeing may come in handy as some employers are less keen on remote working than others. 

If you are unsure of what is feasible, talk to your boss and come up with a plan. If you are already working remotely in your home country, you are in a much better position to negotiate terms.

Sadly, some employers restrict remote work to your home country only. This is typically for legal rather than practical reasons. Some companies are just not set up for it in terms of HR and employee management.

I’ve heard of some larger companies having basically an informal ‘don’t ask, don’t tell’ policy. So long as you don’t create legal headaches or make it too obvious that you’re abroad, it may be tolerated by some managers. Some companies want to allow it in practice but have to keep it in a grey zone while they figure out how to make it more official. It’s up to you to assess what your options are.

Some people just let sleeping dogs lie. I don’t necessarily recommend working remotely in secret, but if you do, make sure to hide your location (I’ll share how).

If there is no way around it, perhaps it’s time to look for a fully remote job. Use sites such as RemoteOK, We Work Remotely, Working Nomads, and Remotive to find the perfect remote job for you. 

You could also go freelance — either by working for clients or working as a consultant for your current employer. Companies with remote teams often structure things this way anyway; receiving invoices from freelancers reduces legal and tax headaches for them (compared to having direct employees working from various jurisdictions).

How to get a remote job

Want the fast track to a nomad life? Then check out the Go Remote Employment Course from my friends at Beach Commute.

This isn’t the sort of course that only waxes lyrically about the nomad lifestyle. What I love about the Go Remote Employment Course is that it’s laser-focused on the practical steps to actually achieve it.

Taught by experienced digital nomads, it’s a structured program all about assessing your career options, showing exactly how to find remote-friendly jobs (and avoid the common mistakes), how to apply successfully, and nail the interview process. 

It even goes deeper into the personal fears that may hold you back and the specific negotiation strategies you can use to get the remote job you want. 

The course normally costs $797 but with the coupon code “indietraveller” it’s 50% off for a limited time.

2. Understand it’s not a vacation

Remote work trips are very different from vacations. Sometimes the line gets blurry, but it’s a good idea to be realistic about the demands of working from locations other than home.

Constantly moving location, as you might on a normal trip, can be a real productivity killer — and it will drain your energy, causing both your work and travel to suffer. Rather than packing and unpacking constantly, it often makes sense to stay in one spot for longer.

Slowing down also has advantages from a travel perspective. Staying in one place for longer will give you more of a chance to get to know the local culture and make connections. You can have a ‘mini life’ in a place that will let you discover things that most tourists rushing through will miss.

Use your weekends and evenings for sightseeing or other activities. If you get into a routine where you wake up early and get the bulk of your work done quickly, you can free up time later in the day to explore — if your work scheduling allows, of course.

3. Keep your location hidden (if necessary) 

In the early stages of the pandemic, a friend of mine gave herself away when all of a sudden a colleague asked her to turn her video on… her background was the lush palm trees of Mexico. Oooops. This definitely got her into a bit of trouble! 

Such a situation is best avoided. Therefore it’s best to be transparent with your employer, though if you want to work remotely without them knowing, it’s crucial to hide your location. (Of course, it’s up to you to assess whether you can or should do this.)

Not giving your location away means setting your Zoom background to blur as well as hiding your internet location.

If you don’t take precautions, your employer can absolutely see if you’re logging in from abroad. Every internet connection has an IP address, which can be traced to a specific country or even city.

To keep this secret, it’s key to use a Virtual Private Network (VPN). A VPN is a secure connection between two networks that uses tunneling protocols to encrypt data.

You have two options. Either use a public VPN, like subscribing to NordVPN, for a basic level of concealment of your location. If your employer has a savvy IT department they might be able to see that you’re using a VPN, but at least they won’t know where you are, so that would give you some nice “plausible deniability”. 

The better option is to use a private VPN. This is a bit technical to set up, but luckily there are services that will do it for you. I wrote about my experiences using KeepYourHomeIP here, which provides you with two small routers and a remote support session to set up a private VPN. When you use this setup, it will 100% look like you are logging in from your home location.

4. Start small — you don’t have to go fully nomadic

Based on social media it seems as if EVERYONE is taking working remotely to the extreme and becoming a year-round ‘digital nomad’. 

But the beauty of working from wherever is that you can choose what kind of lifestyle you want. That could be by the poolside in Bali or from the comfort of your own home with your cat on your lap — or why not both?!

I’ve done the full-time nomad thing and given the right person and life circumstances, it can be truly amazing. It’s also quite a big step to take which keeps many people from doing it. That’s why I think part-time nomading is hugely underrated

You can simply choose to escape the blistery winter months and go remote for a season. Or you can take just a month-long nomad trip. Or why not extend your vacation with a couple of extra weeks of ‘nomad life’? 

This is far less scary than quitting your life and then sailing with the wind.

And if you plan it the right way, maintaining a balance between home/stability and adventure is absolutely possible.

5. Keep your costs under control

It’s a horrible feeling if your remote work trip ends up costing you more than you’re making on the job!

One of the easiest ways to lower your cost is to choose a more affordable destination. Instead of heading to London consider Lisbon or instead of Paris head to Prague. 

Consider subletting your apartment or house while you’re away. The lower your overhead the better.

The longer you stay in one place the easier it also is to keep a budget. When you book a month-long accommodation you are much more likely to get a discount. You can find more tips for finding work-friendly places to stay.

By choosing to stay in cheaper countries, it’s actually possible to have a lower overall cost of life by working remotely from anywhere than by staying at home. 

Those who have become REALLY savvy are staying for free. With websites like Trusted Housesitters, you can find a sweet little gig of minding someone else’s home while they are away and you can stay in their abode for free. It costs around $120 to sign up to Trusted Housesitters and get verified, but then you can stay in places entirely for free for a whole year — usually in exchange for watering the plants or feeding the pets.

As a remote working traveler, you don’t always have to go during the tourist high season. You can grab some off-season deals or discounts that are not as practical for tourists. Doing so can help you save money on flights, hotels, and other costs associated with your trip.

6. Understand the implication for visas/immigration

Depending on your home country, you may (officially) need to obtain a special visa or permit to work and/or travel in countries abroad.

To be honest, what many people do to avoid any sort of hassle with visas and immigration is to enter on a tourist visa… I mean, you are a tourist technically. In practice, this is how 95% of digital nomads travel and work, though the exact legality of it is a matter of dispute. Just remember that if you’re travelling for work and you don’t have a work visa that can be a red flag for immigration officials.

Many countries have begun implementing digital nomad visas to incentivize people to come and stay in their country. These typically allow long stays during which you can work legally without paying taxes there (you simply continue to pay taxes wherever your tax residency is). 

If you’re doing a housesitting assignment through a platform such as Trusted Housesitters, keep in mind this can be regarded as work by border control or immigration. Even though housesitting is done for free, in a legal sense it still counts as work (it’s ‘paid’ with free accommodation). That can mean being denied entry if you don’t have a work visa. 

7. Bring the right gear

You’ll want to make sure you can work comfortably from anywhere. That means bringing reliable gear and a proper work set-up. 

Here are my must-haves:

It can also be worth investing in a travel laptop that’s powerful yet lightweight. You can see some of the best options here.

8. Be 100% sure you can be connected

It’s absolutely critical that you can be online with a stable and reliable internet connection. 

In my guide to finding remote-friendly accommodation, I discuss ways of checking if your Airbnb or hotel has a good enough internet connection.

Just to be sure, I recommend also having a local cellular data plan as a backup. Research the best data plans in your destination and make sure you know how to set up a hotspot so you can switch to mobile in a pinch. You can buy a portable hotspot that takes a data SIM card. 

A small travel router can be a useful tool for staying connected as well. It will let you boost the range of the WiFi in your accommodation, which is sometimes necessary if you want the signal to reach all those fun working spots like the balcony, garden, or kitchen.

9. Respect your company’s IT policies

Some companies prohibit using public WiFi or have special rules for handling confidential information outside the office. Make sure you’re aware of any such policies so you won’t needlessly get into trouble.

If your company requires you to use a VPN for security reasons, that makes it more difficult for you to use another VPN on top to hide your location — but it’s not impossible. 

Check out KeepyourhomeIP.com for a solution that will make it look just like you are logging in from your home even if you’re abroad, while still enabling you to use a company VPN as required.

10. Never set off without insurance

Be sure to get health and travel insurance before you leave home. This will give you peace of mind knowing that if something does happen, you’re covered.

If your employer provides health insurance, make sure to check if it covers you when outside of your home country (it usually doesn’t). 

My favorite travel insurer is SafetyWing, which is specialized in affordable travel insurance for nomads. It includes features such as long-term coverage, virtual doctor consultations, and other benefits specifically geared toward remote workers.

Note: almost all “digital nomad visas” require that you have full health insurance coverage.

11. Choose your destinations wisely

Not all remote working destinations are equal. Good luck trying to upload a file using that dial-up modem in rural Bolivia (I’m speaking from experience here)… it will absolutely make you flee to somewhere else.

It’s a good idea to research your destinations in terms of healthcare system, cost of living, and access to WiFi. My favorite site for this is Nomadlist; it allows you to filter destinations by pretty much any imaginable criteria.

There are some popular hubs of remote work such as Bali, Medellin, and Costa Rica. They’re easy and great for making nomad friends, but less-visited locations may give you a more unique travel experience. 

Using remote work to travel differently

While staying productive on the road takes some practice, working from anywhere lets you travel in a truly different way.

You can stay far longer in known tourist hotspots than a typical vacation and try a mini-life there. Or you can take chances on destinations you might not have otherwise considered.

Perhaps you could stay in a small village in rural Greece. Or maybe work from a surfer beach in Indonesia. Or maybe skip the capital but hit up the second or third city in a country, which are often amazing for getting a taste of the local life. A month in Genoa can teach you more about Italy than those 3 days in Venice.

So be sure to use your opportunities to their fullest and get ready to take your work life and your travels to the next level.

Psst, don’t forget you can get a 50% discount on the Go Remote Employment Course. The knowledge it shares let you bypass most of the initial issues and can give you a competitive edge when applying for (highly prized!) full remote jobs.

Some links may be affiliate links, meaning I may earn commission from products or services I recommend. For more, see site policies.