Part 4: How To Choose a Destination, Estimate Cost of Living, & Find Accommodations When Working Remotely

Once you’ve turned your passion into a profession, it’s time to hit the road. How do you go about choosing where to go first (or next) when options abound?

While experiences differ due to travel expertise, patience, language abilities, income, and what you need to be productive, some destinations are just better suited to working remotely than others.

Investing time and thought into each decision will greatly affect your happiness and overall experience while living and working remotely. Here are some general factors to take into consideration when choosing your next travel destination.

Calculating Your Cost of Living Abroad

Especially when starting out, the lower cost of living your destination allows for, the higher quality of life you’ll get to enjoy.

Here are the tools I use to tell what I’ll spend on an average meal, cell phone service, or the cost of rent before even setting foot on the ground:

  • Nomad List is what many digital nomads consider the definitive location guide. By curating data from websites and travelers, Nomad List gives an overall ‘Nomad Score’ that takes into account scores for cost, weather, air quality, fun, and safety. You browse suggestions or filter your searches to include the basics, or stuff like where the best places to surf are, whether a culture is gay-friendly, or if there are lower reports of racism. Nomad List also features chat forums and detailed for-purchase guides for those looking for additional information about a destination.
  • Numbeo is a huge database of user-contributed data about cities and countries worldwide. It provides up-to-date information about living conditions including the cost of living, housing indicators, health care, traffic, crime and pollution for pretty much anywhere you’d like to go. Data includes such specifics as how much it costs to buy a gallon of milk, a wedge or cheese, or rent a three-bedroom apartment.
  • Expatistan offers a cost of living comparison tool that allows you insight into how much money you’ll need to sustain your current lifestyle in a new location. You can convert your current (or expected) salary to any new city’s level to see how far your dollar will stretch once it’s being spent as a peso, baht or yen. Expatistan also includes a database of international schools, which is extremely handy for those looking to work remotely without sacrificing the quality of their offspring’s education.

Thinking About Costs Beyond Dollars & Cents

While not a cost-of-living index, Speed Test is a vital resource to check out when considering new destinations. Why would I put a global internet speed database alongside these other resources? Because, when you’re working online, you can’t afford much of anything without a stable connection! 

Speed TestMy current connection is stable, but slow upload speeds make for low-quality calls.

In addition to staying sane with a strong internet connection, there’s something else you should consider: safety.

Why sure, a slightly-off-the-beaten-path neighborhood might have appealing rent prices, but saving a few bucks isn’t worth feeling uncomfortable leaving your home after sundown. The above-mentioned Nomad List does a good job of ranking safety. However, double check the Global Peace Index along with the U.S. Department of State’s alerts page to be sure.

How To Scout Out Accommodations

When I started working remotely, I relied heavily on vacation rental websites to find new lodging before I hit the ground. Pricier? Absolutely! However, I’m not really a dorm-style-living/ hostel kind of gal.

But, here’s what I learned: Airbnb, Homeaway, VRBO, etc.—they’re all made for folks going on a vacation.

Not only does that lead to higher prices, even when looking at Airbnb’s sublet section (which gives lower monthly rates), there’s no chance to vet a rental to make sure that it has all the things you need to actually get work done, like stable internet speeds, before plunking down your deposit.

I mean, do you really want a large chunk of your travel change in limbo while trying to navigate a new location?

While you can always get your daily roster of deeds done in a coworking space (Nomad List offers info on these for each destination) or at a coffee shop, you might find, as I did, that you prefer to work in the comfortable quiet of your own home, free from human distractions. (It’s a wonder I’ve survived being so picky!)

This little home in Thailand was amazing… and all of 70 square feet.

Not being able to vet potential accommodations can make booking on Airbnb or similar sites quite tricky, since you generally need to pre-book lest you arrive and find yourself out of options. Plus, booking for a month is really tempting, because the rates are so much cheaper than if you just do a few days!

However, if you throw away the rest of my advice and only listen to one thing, let it be this warning: Don’t pre-book for more than several days.

Don’t pre-book for more than several days.

In each of my experiences traveling to a new destination, I have never, ever extended my stay in the first place I booked.

To the point where I’ve lost an entire month’s rent because the internet did not exist (again, why Bali, why?), it was in a super unsafe neighborhood, the bed was made of rocks, there was a rat infestation (Bali, again, Eat, Pray, Love lied about you), or there was construction happening five feet above, starting at 6 a.m. each day.

My Solution To Securing Accommodations

In my experience, the best thing you can do is scope out a whole bunch of options that you’d like to consider, then contact the hosts to say that you’ll be arriving on such and such date, and would they be available to show it to you once you arrive. Then, book yourself an awesome hotel room for a few days and chalk the first week arriving at any new place as vacation.

After all, you do want a chance to travel a bit too, right?

There are several additional benefits to staying in a hotel for the first few days, aside from enjoying some time off:

  • You get to test the internet in person, which is priceless.
  • You get to pay cash if the host will allow it, avoiding Airbnb or other platform fees.
  • You get to check out which neighborhood you’d like to live in.
  • You get the opportunity to look for local (often less expensive) rentals that aren’t advertised online.

Sometimes, though, following the above just isn’t possible. Maybe you need to make a rush decision. Or, you might think to yourself that a place looks really great, and you’re willing to risk it.

If that’s the case, do yourself a solid: Skype with the host/ landlord and tell them that you want to see a live feed of the place via video chat. Doing so will allow you to get a good feel for what it really looks like and whether the internet connection is strong enough for VOIP calls.

Working Around Airbnb’s Messaging Restrictions

One problem with communicating on Airbnb specifically is that the website blocks any exchange of phone numbers or email addresses. This can make completing the above-suggested voice call pretty difficult.

I’ve gotten around that by telling people to do a Google search for my first and last name—which leads them to my professional website and email address.

It might be worth creating a splash page so that you can tell hosts, “Search for ‘Jane Doe wants to rent your place dot com,’” and put up a little info about you, your needs, and how to best reach you.

If you don’t have the resources to put up a basic domain meant just for contacting hosts, that’s okay. An additional workaround is creating a Facebook page under a unique name, like ‘Jane Doe’s Travel’ and asking hosts to find you there.

A Final Note On Finding Lodging

Craigslist is notoriously filled with scams. But now, other vacation rental sites are seeing an increase too. Before communicating with a host, do a reverse image search on their property to see if it was yanked from a legit listing.

For more in-depth information on avoiding scam listings, check out “How To Spot a Scam Rental.”

Finally, Figure Out Your ‘Big Three’

Much like when considering a romantic partner, it’s realistic to expect that no destination is going to have everything you’re looking for.

That being said, I’ve found it imperative to my sanity to narrow down my personal ‘Big Three’—the three things that tend to make or break my experiences abroad by allowing me to recharge and face the many unexpected challenges.

Sometimes you just really want to scramble some eggs and have to get creative.Sometimes you just really want to scramble some eggs and have to get creative.

What do I look for?

  • Stable internet: Yes, I know it’s been mentioned. However, I’ve found that some remote worker’s definition of acceptable internet differs from my own. Personally, I can’t work without a strong, stable connection of 5 mbps or above. Additionally, I require devoted service and a router within reach, since I’m not going to risk losing a client just because an upstairs neighbor decided to go on a Netflix binge.
  • A gym: Building up your remote business involves a lot of time sitting still, staring a screen. Unless you have a magic metabolism, this can pretty quickly lead to the ‘freelance freshman 15.’ Having a nice gym nearby gives you a chance to unwind in a healthy way, plus an opportunity to make new friends outside of the local watering hole.
  • Fresh veggies: It might seem trivial, but it turns out that having access to fresh greens that I’m familiar cooking with has been an important factor in my overall happiness. Off-sleep schedules and unfamiliar foods can quickly lead to feeling drained and spending too much of your budget eating out. Plus, there’s nothing worse than miming “severe constipation” to a pharmacy clerk that doesn’t speak English.

It might sound trite to place such a value on just a few creature comforts when you’re amped up to travel. But, by knowing yourself and your limits, you can help stave off burning out of the lifestyle you’re working so hard to achieve.

Have you experienced working remotely from another country? Share your tips and stories in the comments below!

Other articles in this series:

  • January 20, 2016

Autumn Yates

Autumn draws from a reporting background and years of experience working remotely, while living abroad, to focus on topics in travel, beauty, and online safety.


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