How To Choose Your Next Digital Nomad Destination: Remote Work and Travel

People often ask us how we choose our next destination as digital nomads, so I thought we could take the opportunity to share our thought-process and a few resources we use to plan our remote work and travel.

The process for choosing a digital nomad destination is slightly more specific than how to choose a travel destination. And the best “workation” or digital nomad destinations for one person may be completely different for someone else.

For further reading:
– What is a digital nomad?
– A day in the life of a digital nomad
– How we make a living as working nomads

Updated: 2020. Originally published: 2015

Our Steps for How to Choose Our Remote Work Destination:

1. Determine the purpose of the trip
2. Research desirable areas
3. Find an ideal living situation
4. Check for award tickets
5. Secure discounts
6. Book the trip

Determining Trip Purpose for a Digital Nomad Stay

When you can work anywhere in the world (as long as there’s wifi), you need to narrow down your purpose to find the best remote work destination. For example, your trip goals could include:

– A warm, sunny climate
– Meeting like-minded locals or digital nomads
– A quiet place to focus on a big work project
– Saving money on living expenses
– Practicing a foreign language
– Developing a skill or hobby

Case Study: As an example, I’ll share our thought process for choosing to stay in Cuenca, Ecuador for six weeks in 2015.

We always strive to learn and grow through our travels, and one of our life-long goals has been to learn multiple languages (like Spanish, French, and Japanese). We decided it would be motivating to schedule a stay in a Spanish-speaking country. That way we could start studying in preparation, take classes when we arrived, and be immersed for a few weeks.

Some secondary purposes of our trip are:

• Experience someplace new
• Be in a warmer/milder climate during the winter
• Have access to internet good enough to continue our online work
• Keep our expenses low

Digital Nomad or Workation Destination Research

Below are some tools and resources I use to research new remote work destinations around the world.

Cost of Living Abroad: Finding affordable destinations

As digital nomads who live on a tight budget, a destination’s cost of living is a primary concern. So we started our search by looking at cities where we could potentially save money compared to our normal living expenses in the States.

Check Numbeo: This map on Numbeo shows a cost of living index rating for cities around the world. For example, Cuenca’s consumer price index is 52.23, whereas Portland’s is 80.71 and Honolulu is 99.09.

It will even tell you the average price for certain items – like a soda at a restaurant, a pound of potatoes at the market, a one way ticket on local transit, rent for a one-bed apartment in the city center, and a host of other things.

Check Nomad List: Nomad List gives cities ratings for monthly cost of living, weather, air quality, internet speed, and safety.

Case study continued: According to the Nomad List profile of Cuenca, the monthly cost for a nomad is $777, average internet speed was 4 Mbps (which is not great but we found an Airbnb apartment that confirmed faster speeds), and the weather tends to stay around 70F all year.

Once we had narrowed our search to Latin America, I also did a Google and a Pinterest search for “best digital nomad destinations.” A couple bloggers had shared positive experiences staying in Cuenca and mentioned the charming UNESCO World Heritage city center, a good selection of cafes, and ease of transit. Plus, it’s not far from Ecuador’s largest site of ruins, Ingapirca.

Further reading: Best Off the Beaten Path Digital Nomad Destinations

Personal Network

When we first became digital nomads, every international destination we visited was home to someone from our personal network. We’ve found that this really helps us develop an authentic cultural connection quickly in a new place and often helps out financially when we can stay with friends and family or share meals together.

When we were deciding where to go, the fact that I had a friend from my MBA program living in Quito tipped the scales. So we were welcomed and oriented by native Ecuadorians before heading out on our own – a huge bonus!

Travel Discounts

There are three significant areas where travelers can save money:

1. Flights (more on that below and in our e-newsletter)
2. Accommodations (more below and in our book)
3. Activities

When living and working abroad, local life – grocery shopping, going on walks, occasionally eating out – makes up the bulk of our activities.

These are the same expenses we would have back home. We’re not paying for tours or museums every day, as you might on vacation. 

That being said, if there is an activity or attractions we really want to do, I always look for a deal.

Case study continued: When we settled on Ecuador as a destination, I started researching potential schools to do Spanish lessons. This was a bit of a splurge for us, so cost was a major factor. I chose three promising schools based on reviews and e-mailed them an informal pitch. I simply asked if we could get a discount on classes in exchange for sharing our experience of their school on our blog.

Fortunately, one of the schools offered us a great discount. They are a non-profit institution that does an intensive, individualized week of Spanish language and cultural immersion. So we’ll be staying a few days in a homestay, doing 20 hours of personalized lessons, and participating in cultural field trips together. We’ll tell you all about it when we get there!

Accommodations and Amenities

Having secured a spot in a Spanish school in Cuenca for our first week, I started researching neighborhoods in town. I knew the school was in a nice part of the Old Town, so I aimed to find more accommodations around there.

My go-to for our digital nomad stays is Airbnb, where many listings provide a discount for one month stays (28 days or more).

Peek into our Airbnb stays around the world here >

I searched Cuenca Airbnb’s for a one-month period using these filters to narrow it down:
– entire home/apartment
– wifi
– kitchen
– price under $625 per month
– check “search as I move the map” and zoom in on Cuenca Old Town
– at least 4.5 stars with multiple reviews

I found an Airbnb host that oversees a handful of properties and each one had excellent reviews. One apartment unit in particular was in a central but quiet part of Old Town, with free laundry in the building, and 8Mbs internet.

The nice thing about Airbnb is we don’t have to rely on the host’s description of the property because all of these things were confirmed by 20+ guest reviews.

Save money, work smarter, travel deeper with
our free Resource Guide for Digital Nomads.

Book the Trip for Remote Work Abroad

Before finalizing any of our arrangements, we had to make sure that we could get to and from Ecuador using airline miles. (Thanks to travel hacking, we don’t pay anything but fees for international flights.)

I searched for award flights online using the airlines where we had a good stock of miles: United, American, and Alaska.

Alaska and American partner with LAN for many of their South America award flights, and unfortunately these cannot be viewed or booked online. So I used LAN’s website just to see what flights might be available from Portland. If I had found something on LAN that looked good, I could have called Alaska or American to book the flight (using Alaska/American miles on a LAN-operated flight).

As it happened, I found an Alaska/American flight through Miami on AlaskaAir.com without using LAN.

Once all of the key pieces of our plans are looking good, it’s time to book:

1. Book flights using award miles
2. Book accommodations
3. Book other key transportation
4. Confirm any key activities that need advance notice

I used our Alaska miles to book a one-way flight to Quito. I booked a return flight a little later (but still in advance of the trip), once we had determined where we’d go next.

Then I confirmed our week with the Spanish school in Cuenca and our month stay in the Cuenca Airbnb.

To get from Quito to Cuenca, we could either take a short flight or a longer, cheaper bus ride and potentially stop somewhere along the way. With help from our friend in Quito, we ended up taking the long-distance bus, and it was great!

So that’s our plan and process.

We loved Ecuador and Cuenca has become one of our favorite digital nomad destinations. We now have blogs about Cuenca’s food, Spanish lessons, day trips, and other beautiful destinations in the Andes.

Read more about digital nomad life:
– What is a digital nomad?
– A day in the life of a digital nomad
– How we make a living as working nomads
– Our top digital nomad business tools
– My portable ergonomic laptop set up
– Long term travel clothing packing list

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