Ask a Digital Nomad: How Do You Choose Where to Go Next?

Welcome back to my digital nomad series, in which I ask 4 – 8 location independent professionals to answer a question about the digital nomad lifestyle. The point? We all do it a little differently. There’s no right answer. Our unconventional lifestyles are distinctly our own.

Today’s topic is how do you choose where to go next? When the whole world opens up to you, how do you decide where to live, work, and play?

Here’s what a handful of location-independents had to say:

Gigi Griffis

Hey again, it’s Gigi—a long-time (4.5+ year) digital nomad, architect of this little slice of the internet, book author, and content strategist/copywriter/coder. I travel the world with my pint-sized pooch, Luna, and my boyfriend, Chad. In my free time, I swoon over new foods, hike tough trails, take too many photos, and read a lot of books.

Originally from: Virginia Beach, VA, USA

Before nomading, I lived in: Denver, CO, USA

Been on the road for: 4.5+ years

First stop on the road: Edinburgh, Scotland

How did you choose that place?
When I first started talking about my intention to travel and work from the road, my therapist asked me this: If you could go anywhere, not worrying about clients or time zones or any of that, where would you go? The answer resounding in my heart was Europe. I wanted to see every nook and cranny of Europe, so I started making a list of places.

Edinburgh was one of the top places on the list (mostly because the photos were beautiful) and it made the most practical sense as a starting point. I wanted to spend more than three months in Europe, which meant I had to spend at least part of my time outside the borderless schengen zone (which encompasses most of mainland western Europe and only allows USers 90 days on a tourist visa). The UK is outside the schengen, it would require one of the shortest (and cheapest) flights to get to, and I was certain I’d have the amenities I needed to get work done. It seemed like a logical first stop, so I booked a month in a guesthouse just outside the city center and started there.

A few favorite stops along the way: Paris, France; Lauterbrunnen, Switzerland; and Kobarid, Slovenia.

How did you choose to go to those places?
I went to Paris the first time because a friend of a friend lived there and offered to host me. I liked the idea of seeing Paris, the idea of having a free place to stay for a few days, and the idea of having some companionship, so Luna and I headed to the city of light for a few days before moving on to a conference in Spain. I’ve since been back to Paris many times, sometimes because I just needed some girl time and my original hostess has become a good friend and sometimes because I had an opportunity to pet-sit or stay cheaply.

I chose to spend my first vacation on the road partly in Lauterbrunnen, Switzerland (a valley with 72 waterfalls), because I’d traveled there a few years before with my best friend. I loved everything about that little Swiss town with its giant cliffs and towering mountains and bright green meadows, so I went back. And then went back again. And then eventually applied for residency and lived there for two years because I loved it so much.

As for Kobarid, I chose it for its beauty. I knew I wanted to spend part of the summer in Slovenia in 2015, and when I started researching possible bases, one that jumped out at me was the Soca Valley, home to a perfect turquoise river, tall, imposing mountains, and pretty mountaintop churches. As I went through the list of places in Slovenia that might be interesting, I looked each one up on Flickr. The Soca Valley won the “most beautiful photos” contest for me, and so I started looking into Soca towns. I had the good fortune of being connected to a couple Slovenian locals, so I asked which town in the valley they recommended. Kobarid, they said, was the prettiest. I was sold.

Currently in: Rome, Italy

How did you choose that place?
After spending most of 2016 in North America, I knew I wanted to get back to Europe. It’s the place where I feel most at home. Chad and I had decided to stay in Vancouver until early December so that we had plenty of time to wrap up work, re-gear, attend some tech conferences, etc., then head to Europe in December for vacation and then get back to work in January. Since December and January are winter in Europe and neither of us wanted extreme cold, one of our requirements for a first stop was that it be southward and relatively temperate. Chad also requested that we base ourselves in a city where he could take advantage of co-working spaces, tech meetups, and city amenities.

I proposed Rome, Paris, and Lisbon as possibilities. Paris would be potentially rainy and chillier than the other two, but it had a lot to offer in terms of amenities and connections. Lisbon I hadn’t been to, but Portugal is on my list. And Rome I knew I loved in the winter, with its often-sunny and sometimes even warm days, it’s amazing food, and an already built-in community of people I know and adore. With my glowing recommendation, Chad picked Rome as our base city.

Are there any other strategies you use to choose where you’ll travel?
Sometimes I travel to be near friends (like this winter in Arizona, many of my trips to Paris, and my frequent choice to pass through Pennsylvania whenever I’m in North America). Sometimes I chase good weather, heading toward sunnier spots in the winter and racing northward away from the hot-hot-hot in the summer. I always have to keep in mind the length of stay rules (particularly in the schengen, since I spend so much time in Europe) and sometimes those drive me out of one particular region and into another. Sometimes Chad requests a city or a mountain location or sunshine and we plan accordingly. And frequently I just go with my gut.

Find me…well, here at gigigriffis.com. Also: Instagram and Facebook.

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Sam Kelly

I’m Sam—a global citizen spreading smiles daily and engaging my creative tenacity because I know there’s nothing that can’t be done! I am a Boliviana-American, adopted from my orphanage as a baby. I grew up in Maryland and went on to earn my BFA from the Tyler School of Art at Temple University in Philadelphia. This past February, I resigned from my job and went from desk to backpack, spent Valentine’s Day in Rome, my birthday in Guatemala, and Thanksgiving in Barcelona.

Originally from: La Paz, Bolivia

Before nomading, I lived in: Southwest Florida, USA.

Been on the road for: Nine months

First stop on the road: Rome, Italy

How did you choose that place?
I had just left my full-time job in Florida and taken a 10-day trip to Philadelphia, when I managed to score $400 round-trip tickets from the states to Rome. Before I knew it, I was up in the air and out on the road less traveled. Rome was my base for a two-plus month trip to Europe.

Initially, my mother and I visited Rome in summer 2015 and I’ve been enchanted ever since. From the daily gelato and Italian cuisine and company to exploring ruins to looking directly into Papa Francisco’s eyes (I could have high-fived him during a Wednesday audience) and gazing at Michelangelo’s works that could bring me to tears, Rome is one of my favorite songs and I would gladly play it on repeat any given day.

A few favorite stops along the way: My orphanage, Bolivia; Burano, Italy; and San Pedro La Laguna, Guatemala.

How did you choose to go to those places?
Traveling back to my orphanage was always something I wanted to do. Growing up, I would talk about my orphanage, knowing that it existed, knowing my story began there, yet separated by miles and memories of my mother and aunt, who journeyed to La Paz to adopt me when I was a baby. When my college, Temple University, offered a study abroad program there with the International Design Clinic, it was fate, a long-time-in-the-making homecoming. My soul is still very much there and I am fortunate to have journeyed back twice.

Burano, Italia: Venice is great, but for me, Burano is way better. An hour north of mainland Venice, it’s so beautiful that it makes leaving Venice easy. The buildings are multicolored and the vibe is a sleepy fishing town after dusk when most of the tourists have gone home. You still get the Venice feel of an island, except with striking colors. It’s so beautiful that you just have to see it for yourself and be a part of the artist palette. I stayed in Venice for over a week and went to Burano nearly every day, it’s an artist’s playground.

San Pedro La Laguna, Guatemala: Coming off my Europe trip this past spring, I buckled down to my goal of becoming fluent in Spanish. After reading reviews of Spanish schools in Guatemala, Colombia, Bolivia, Madrid, and a few other places, I decided on San Pedro off Lake Atitlan, Guatemala. I got to live on a volcano and run up it daily, kayak to my heart’s content, have stable wi-fi for my online work and find a supportive community. There’s a big part of me that wants to move to NYC while I’m young and still relish the 3 a.m. nights, yet when I think of San Pedro, it’s easy pace of life is very enticing as well; it fits me too. When I’m there, I am welcomed like an honorary Guatemalan (which I’m often mistaken for). San Pedro is known for locking people in (some claim it’s the magic of the lake). I met many travelers who had planned to stay a couple weeks and ended up staying months and others who planned to stay a few months and stayed a few years!

Currently in: Barcelona, Spain

How did you choose that place?
Partially because I wanted to continue my Spanish and partially because I wanted actual sangria and paella and Barcelona nights. There’s American-made paella and it’s just not the same (in the same way the best pizza can only be found in Naples, Italy). Barcelona is currently my base for this Europe trip.

Are there any other strategies you use to choose where you’ll travel?
The best strategy is to be completely flexible (think Skyscanner “everywhere” option). The second best strategy is to not hesitate when you find a deal. I scored an under-$100 direct flight from Miami to Oslo (Norway), which has been my best flight win to date (beating out a previous Florida to Chicago round-trip flight for $33). If I had a waited until the next day the price would have been over $1,200.

I’ve found it’s best to book in euros, surf incognito with cleared cached/cookies, use Google’s API Matrix, and book international flights on Saturdays (and US domestic flights on Tuesdays).

Find Sam on Twitter and Facebook. 

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Harris & Andrea Fellman (+ Family)

We’re the Fellmans—Harris, Andrea, McKenna, and Hudson—a location-independent family of four currently hanging our hats in Barcelona, Spain, where we’ll base out of to explore Europe for the next two to three years. We’re slow travelers, basing ourselves in one spot (previously: Guanacaste, Costa Rica, and currently Barcelona, Spain), enrolling the kids in international schools, and exploring outward from there. We’re big fans of travel, community, outdoor adventures, style, and, of course, family-friendly places.

Originally from: Minneapolis and Florida.

Before nomading, we lived in: Pasadena, CA, USA

Been on the road for: Semi-nomadic since 1996

First stop on the road: Barcelona, Spain

How did you choose that place?
Oh, I don’t know…we probably threw a dart at a globe or something. Before we were married, we traveled around Europe for a month and had never gotten down to Spain. Barcelona looked amazing: prices were good, internet was good, and it was well-located to other places in Europe we might like to get to as well. (Although, Barcelona turned out to have plenty to see and do on it’s own for a month with kids.)

A few favorite stops along the way: Lake Atitlan, Guatemala; Trinidad, Cuba; Interlaken, Switzerland; and the beaches of Guanacaste, Costa Rica

How did you choose those places?
Alright, well the only place we didn’t choose by simply saying “where should we go to next?” is Guanacaste, Costa Rica. That’s the place we first moved when we decided to go full nomad.

With kids, we felt there were a few different ways to do it: 1) Travel the world for a year, go to a different country every month, and road-school the kids. 2) Same as above, but go to a different location every three months. Maybe find schools that’ll take the kids for a few months at a time. (But then that didn’t really seem fair to them.) Or 3) move to a different region for at least a year, put the kids in school, and travel out to different countries from there.

Option three was more our style. We had been to the Guanacaste area of Costa Rica before, so when we finally decided to make the move, we visited one more time, found a fabulous realtor (Randy Toltz) who showed us around, told us about the schools, and a year later we made the move.

We felt Costa Rica would be an easy first move: it’s a quick trip to and from the USA and on the same time zone. Plus, we had never been anywhere in Central America other than Costa Rica and wanted to check some spots out.

We lived in Costa Rica for three years and traveled out from there. There is a community of expats there that we absolutely are in love with. The beaches are still unspoiled. The life and lifestyle is idyllic.

Lago de Atitlan, Guatamela, and Interlaken, Switzerland, stand out to me as being one of the most breathtakingly beautiful places in the world. We also met one of our very good friends back in 2000 while traveling to Interlaken.

You’ve heard that Havana, Cuba, is stuck in time in the 1950s…well, Trinidad, Cuba, is like traveling back in time to the 1600s (well, except for the cars). Cobblestone streets, old Spanish pubs, wonderful people, rich in history.

Currently in: Barcelona, Spain

Where we plan on staying for two to three years, at which time our oldest will be in high school, so our decisions will change a bit and focus around that.

How did you choose that place?
We’ve loved Barcelona since the first trip here eight years ago. For a bit, it was between Spain and Italy for us, but Andrea felt we’d like Spain more.

So, we went on a recon trip last summer, traveling all over Spain–from Madrid to Grenada, Sevilla, Valencia, and finally Barcelona. We loved the rest of Spain so much, I was literally concerned that we might not like Barcelona as much as we remembered.

But from day one landing in Barcelona last year, we just fell in love with the city all over again.

Are there any other strategies you use to choose where you’ll travel?
We pick a long-term location that has other short-term locations that we want to travel to nearby. We’re ready to eat, play, and shop all over Europe right now!

Since we have kids, the one thing we have to make sure of is that there are good schools in our long-term location (we put them in international schools) and fun stuff to do for them in our short-term destinations.

And lest anyone thinks this is all sangria and siestas in Spain, let me tell you, the transition to living here was much tougher than we thought it would be. We’re finally getting settled in and making our winter travel plans. But that’s a story for another interview.

Find Harris and Andrea at wanderlustliving.com and trafficforme.com.

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Radhika

I’ve been a full time traveler and digital nomad since 2013. A massive foodie and a coffee addict, I often skip a tourist sight to try the local food instead. I travel the world while running a digital marketing business with my partner, Johnny, blogging about digital nomad life along the way.

Originally from: India, via Australia.

Before nomading, I lived in: Gold Coast, Australia

Been on the road for: Just over three years

First stop on the road: Medellin, Colombia

How did you choose that place?
It was based on a lot of good things I had heard from friends but also because we really wanted to go to South America at the time. Medellin ended up sounding like the perfect place to start because it was not only cheap but the city also has good weather, good internet, easy availability of short term apartments, and it was the perfect place to practice our Spanish.

A few favorite stops along the way: Guadalajara and Mexico in general.

How did you choose to go to those places?
I had never heard of Guadalajara until a girl I met in Peru told me she was living there. After talking to her about it further and doing more research, I went there just to “try it out,” ended up falling in love with it, and went back in again the following year.

As someone who works online, the internet is obviously one of the major factors when choosing a place to live/set up base in. Guadalajara has an excellent co-working space (Nevermind), so that was ideal for me to work from. Also, I like to live in a place for a few months at a time, so the place has to be interesting enough and Guadalajara did not disappoint! Its a fun city with lots to do not only in the city itself, but in the surrounding area; there is so much to explore, including places like Tequila and the Pacific coast.

Currently in: Chiang Mai, Thailand.

How did you choose that place?
I spent six weeks in Chiang Mai in 2014 and this time around when I was looking for a place that would be easy and peaceful, it was the first place that came to mind. Chiang Mai, as many digital nomads will tell you, is a very easy place to live. Internet, coworking spaces, apartments, food, safety – it ticks all those boxes so you don’t have to struggle too hard to settle in and make yourself at home. It’s big enough so you don’t get bored but small enough not to get overwhelmed by.

Are there any other strategies you use to choose where you’ll travel?
I travel slow and usually choose a place where I can set up base for a few months and explore in and around that area. I also like places that are stimulating to live in. I like to immerse myself and get to know a culture and its food through the place I live in. So the place has to have good internet and/or co-working spaces obviously, but also opportunities for me to make local friends, eat local food, and experience local activities that go beyond the usual tourist trail.

Being able to maintain healthy habits is also important for me, so when choosing a place, I also look up the availability of gyms/ yoga studios as well as local produce markets and supermarkets so I can cook at home.

It’s important to know yourself and know what you need to live a lifestyle you enjoy and pick places accordingly. Long term travel is different from going on a holiday, so while a remote beach might be a great vacation destination, it might not always be the perfect choice for being a digital nomad (not for me, at least.) So always do plenty of research and don’t just go to a place because every other digital nomad says you should.

Find Radhika on Instagram, Facebook, and Fulltime Nomad.

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LaToya Allen

My name is LaToya. I split my time between working as a software engineer at Big Cartel and building SheNomads, a community of folks interested in remote work, travel, and tech.

Originally from: Michigan, USA.

Before nomading, I lived in: Chicago, IL, USA (where I still keep an apartment).

Been on the road for: Just under a year.

First stop on the road: Mexico City, Mexico

How did you choose that place?
I was supposed to go to Panama, but there was a problem with the name on my ticket. They swapped my last name for my first name and I didn’t catch it until I was supposed to leave for the airport! United wanted to charge me $700 USD for the name change, so I decided to book a flight to Mexico City with a different airline for a third of the cost.

A few favorite stops along the way: Lisbon, Portugal; Oslo, Norway; and Tel Aviv, Israel.

How did you choose to go to those places?
Lisbon: I wanted to stay at a nice co-living co-working space and found Surf Office. I built my trip around staying at their Lisbon location.

Oslo: It was cheap to fly back to the US from.

Tel Aviv: I knew someone who was currently living there and I wanted to go somewhere that wasn’t considered a popular digital nomad city.

Currently in: Chicago

How did you choose that place?
This month my company launches Office Hours. On Wednesdays, we have AMAs sponsored by tech companies. On Saturdays, we have online classes and workshops. There are a lot of moving parts to Office Hours, so being in Chicago where I have little distractions, strong wi-fi, and a set routine was a must.

Are there any other strategies you use to choose where you’ll travel?
There are three main factors: price, friendships, and responsibility. If something is reasonably priced, I have digital nomad friends there, and I don’t have to be online to teach a class, I’ll go. If it’s a more expensive city, I won’t get to see any of my traveling friends, and the wi-fi is terrible, I won’t.

Find more from LaToya on her podcast, shenomads.com, Facebook, and Twitter.

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Carole Rosenblat

I’ve worked in travel and tourism most of my adult life–from working on board cruise ships for eight years to leading camping/adventure tours across the U.S. and Canada, and managing high-end international tours as well as corporate meetings around the world and even serving as the Director of Fun for a hotel. Though I’ve been writing professionally for eight years, I went “all in” nearly three years ago with the creation of Drop Me Anywhere, an interactive reading and writing website about unplanned travel where I crowdsource the destinations by inviting readers to vote.

I also volunteer in each location and profile the organizations on my philanthropic website, Rebel-With-A-Cause. I’m now writing a humorous travelogue based on my two years doing the project non-stop, as well as planning a Female Empowerment Mission Summit (F.E.M.S.) to help women of all ages do their “one big thing.”

Originally from: Detroit, Michigan, USA

Before nomading, I lived in: Phoenix, Arizona, USA

Been on the road for: About two years.

First stop on the road: Berlin, Germany

How did you choose that place?
I didn’t! My virtual travel buddies (readers of my blog, Drop Me Anywhere) chose it for me by voting for me to go drink gluwein, which I did at the many Christmas markets across Germany.

A few favorite stops along the way: Budapest, Hungary, and Gili Air Island in Indonesia

How did you choose to go to those places?
I just put up themed votes on the website and my virtual travel buddies do the rest. Sometimes I’m happy with their decision and sometimes, not so much. But sometimes, I end up really liking the places I least wanted to travel to.

Currently in: Phoenix, Arizona

I’m currently in Arizona trying to sell my house. I’ve just returned from guiding a three-week tour of U.S. National Parks and am leaving for Cuba in 10 days to lead a tour there. Hopefully, I’ll be attending the World Travel Market Conference in London at the beginning of November and maybe lecturing to travel and tourism students at a university in London in December. I might spend some time in Budapest to finish writing my book on the Drop Me Anywhere experience and, when I sell my house, I will probably put up a few more votes for readers to choose destinations where I’ll travel without a plan.

How did you choose that place?
I’m here to sell my house.

Are there any other strategies you use to choose where you’ll travel?
Here and there, I travel to visit friends and family. Also, some places are less expensive to spend time in, so that’s also a consideration when I’m making my own decisions. And, as I write for online and print publications, sometimes I go where I see a story I could sell.

Find Carole at Drop Me Anywhere and Rebel With a Cause.

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Any other full-time traveler types out there? How do you choose your destinations?