We Asked 14 Digital Nomads To Share Their Favorite Cities and Airports
What makes a city – crushing crowds, traffic, big shiny buildings stacked to the horizon? They’re riotous and anarchic, clean and orderly, connected to nature or cut off from the surrounding environment. Their communities can feel close-knit or atomized, sometimes both in the same day.
Cities aren’t just one thing. Each one is its own thing.
So maybe that’s why there was no consensus favorite among the digital nomads and pro travelers we asked. In fact, if there is a consensus, it’s that we’re not ready to settle on just one.
Read on for 14 digital nomads’ takes on their favorite cities and the airports that bridge between them.
DIGITAL NOMAD/TRAVELER PROFILE
Derek baron, wanderingearl.COM
Digital Nomad Derek Baron at the top of a mountain
WHAT’S YOUR FAVORITE CITY?
I don’t have one favorite above all others but I have a special connection with Melbourne, Australia. It’s where I studied abroad for a semester in university and it was that experience that opened my eyes to countries in Asia that I knew almost nothing about. This sparked my interest in travel and is the sole reason I went on my first solo backpacking trip to SE Asia back in 1999. I also have a lot of friends in Melbourne, I find it to be a beautiful city where it is very easy to meet people, it has endless activities and events, both in the city center and its surroundings and, to me, it just has a very appealing overall atmosphere.
Favorite airport?
Dubai, simply because it is the most diverse location on the planet and as a result, the single most fascinating place to partake in people-watching. Every corner of the globe seems to be represented in every terminal of that airport. It’s not always the easiest airport to fly in and out of or to change planes in but the people-watching opportunities more than make up for it!
DIGITAL NOMAD/TRAVELER PROFILE
James Clark, nomadicnotes.COM
Digital Nomad James Clark on sand dunes in the Sahara
WHAT’S YOUR FAVORITE CITY?
I nominate Saigon given I have spent the most time there over the last two years. It’s not everyone’s cup of tea, but I like my cities big and chaotic, and the street food scene there is among the best in the world.
FAVORITE AIRPORT?
Singapore Changi. It’s a comfortable place to overnight it and you can find reasonably-priced food (for an airport). It feels very homely (again, for an airport) with its warm carpet pattern and little nooks to chill out.
DIGITAL NOMAD/TRAVELER PROFILE
LIz Carlson, youngadventuress.COM
Digital Nomad Liz Carlson of Young Adventuress on the slopes
WHAT’S YOUR FAVORITE CITY?
New York. It has it all, and I never get tired exploring there. FAVORITE AIRPORT? Probably Queenstown here in New Zealand, mostly because it’s so small you only have to arrive 30 minutes before your flight departs, there is no security and you can park outside it on the main street, avoiding parking fees, and just walk in. When you fly out, you go over Lake Wakatipu and over the Remarkables, the local mountain range. So not only does it feel like you are getting a scenic flight whenever you take off and land, it also has to be the most convenient airport in New Zealand.
DIGITAL NOMAD/TRAVELER PROFILE
ROB HANLY, ROBHANLY.COM
Digital Nomad Rob Hanly poring over maps
WHAT’S YOUR FAVORITE CITY?
Berlin in Summer, Chiang Mai in Spring, and Medellin for the rest of the year.
FAVORITE AIRPORT?
Singapore, if only for their sleeping areas.
DIGITAL NOMAD/TRAVELER PROFILE
Conni biesalski, connibiesalski.COM
Digital Nomad Conni Biesalski sipping some fresh juice at a cafe
What’s your favorite city?
I don’t actually don’t have one. But if I had to name one, I guess it would be San Francisco.
Favorite airport?
Amsterdam Schiphol.
DIGITAL NOMAD/TRAVELER PROFILE
Amit Gupta, amitgupta.COM
Digital Nomad Amit Gupta rolling with his best friend
WHAT’S YOUR FAVORITE CITY?
My favorite city is one I’ve never been to. The first time I visit a place is always the most magical.
FAVORITE AIRPORT?
Singapore. There’s a free tour bus around Singapore if your layover is long enough. There’s tons of places to sleep or shower, multiple 24hr movie theaters, a rooftop pool, an orchid garden, a koi pond (two, actually). A butterfly garden! We did a layover here for our company Workcation to Thailand in 2013 and made a custom guide for everyone just because there was so much to do during the layover.
DIGITAL NOMAD/TRAVELER PROFILE
Clay Hebert, Clayhebert.COM
Digital Nomad Amit Gupta rolling with his best friend
What’s your favorite city?
I’ll always love New York City. Once you’ve survived in the belly of the beast, every other city looks like it’s moving at half speed. But that mandatory hustle can weigh on your soul and right now, San Diego is my favorite city in the U.S. It’s absolutely gorgeous here. The weather is consistently perfect. The people are laid back, and there is a burgeoning entrepreneurial scene. We’re surrounded by nature. We live with another couple in a 6BR house on 2 acres. We have a huge pool, a waterslide, a zipline and a treehouse that’s been featured on TV. Being in nature is part of the SoCal lifestyle, which is different than Manhattan, where you have to schedule an appointment with nature…(OK…I’m going to Central Park at 7am on Thursday.) Two weekends ago, we surfed in the morning and hiked a mountain in the afternoon. In the winter months, you could easily go surfing and snowboarding in the same day. Staying active is much easier here. Some of the top online marketers, podcasters and creators live here, and that’s not a coincidence. When you work online and can live anywhere, this is a pretty great choice. San Diego is perfect. Wait, don’t print that! I don’t want everyone to read that and move here. But please come visit!
FAVORITE AIRPORT?
In the U.S., I do love San Diego’s airport. It’s actually the busiest single-runway airport in the U.S. and second busiest in the world behind Gatwick, yet it feels small. Some gates are only a few yards from passenger pickup. Plus, it’s located right in downtown San Diego, so it’s not only convenient, but parts of downtown are like standing on the runway. It’s fun to look up and see planes landing every few minutes. In Europe, I like the Frankfurt airport. The clean and smart design is quintessentially German.
DIGITAL NOMAD/TRAVELER PROFILE
Mckel hill, nutritionstripped.COM
Digital Nomad Mckel Hill of Nutrition stripped chopping vegetables
WHAT’S YOUR FAVORITE CITY?
Hands down, Nashville! Although I have a hunch when I visit LA, the warm weather and health/wellness atmosphere will have me completely smitten.
Favorite airport?
Cincinnati, it reminds me of home.
DIGITAL NOMAD/TRAVELER PROFILE
Eytan levy, snarkynomad.COM
Digital Nomad Eytan Levy the Snarky Mountains in the mountains
What’s your favorite city?
Hmm…at this point, I’m not sure. A lot of my trips have been to relatively inexpensive countries, just for budget reasons, so I would have to visit some of the more modern cities in places like Western Europe to compare.
Favorite airport?
Every Asian airport I’ve ever flown through has been better than any Western equivalent. So much better.
DIGITAL NOMAD/TRAVELER PROFILE
Matt Long, Landlopers.COM
Digital Nomad Matt Long of Landlopers on the ice in a parka
WHAT’S YOUR FAVORITE CITY?
Paris, purely for emotional reasons. It was the first foreign city (not in Canada or Mexico) that I visited when I arrived as an exchange student in high school. It was a wonderful experience and further cemented what I always knew – that travel and learning about foreign cultures was what I wanted to do with my life.
Favorite airport?
Hong Kong, because I think that the Cathay Pacific lounges are the best in the world.
DIGITAL NOMAD/TRAVELER PROFILE
Kimberly Rich, theboldlifemovement.com
Digital Nomad Kimberly Rich of the Bold Life Movement in Iceland
WHAT’S YOUR FAVORITE CITY?
Tokyo and Rome come to mind for different reasons. Rome is undeniably romantic, and I love the history and the food it offers. Tokyo is unlike anywhere else, and truly embodies the appeal of travel for me. It’s so different from what I’m used to and would take decades to even scratch the surface.
Favorite airport?
LHR [London Heathrow]. I associate this airport with flying standby on my Dad’s former airline for last minute International trips. Even though it’s massive and hectic, it makes me feel spontaneous and cultured and truly alive.
DIGITAL NOMAD/TRAVELER PROFILE
Josh skaja, fretboardanatomy.COM
Nomadic Musician Josh Skaja of Fretboard Anatomy on stage-min
WHAT’S YOUR FAVORITE CITY?
I travel so much domestically that I don’t get to do as much international travel as I’d like, so this is heavily US-centric. I’m basically always on foot, and I’m mostly looking to eat great food and hear live music. I love me some New Orleans, Portland (Oregon), NYC and my hometown of Chicago. Raleigh, San Diego, and Austin great too.
FAVORITE AIRPORT?
I don’t know that I have one, so let me talk about the relative merits of the two Chicago airports. If you’re flying internationally, you don’t have much choice in the matter–you’ll be flying in and out of O’Hare. It’s busy, chaotic, and the traffic sucks. But badass chef Rick Bayless has two of his Tortas Frontera restaurants here, and that almost makes up for it. Terminals 1 and 3. If you’re going domestically, you’ll probably be a lot happier flying out of Midway–fewer delays, less traffic, shorter TSA lines. The food scene is less exciting, but it’s the airport where Southwest (my preferred airline) is. I’m basically always on foot, and I’m mostly looking to eat great food and hear live music. I love me some New Orleans, Portland (Oregon), NYC and my hometown of Chicago. Raleigh, San Diego, and Austin great too.
DIGITAL NOMAD/TRAVELER PROFILE
derek sivers, sivers.org
Derek Sivers on stage
WHAT’S YOUR FAVORITE CITY?
Depends on the need: New York when feeling super-ambitious, social, and connected. Los Angeles when feeling super- ambitious, but also needing silence and space for inward-focus, yet still being where things are happening. Singapore for the fascinating mix of people and outward-focus to the surrounding area. London for a perfect balance of all of the above.
Favorite airport?
Singapore, by far. I can’t think of any other airport I’ve ever really liked.
DIGITAL NOMAD/TRAVELER PROFILE
Colin wright, exilelifestyle.com
Digital Nomad Colin Wright of Exile Lifestyle speaking from the stage
WHAT’S YOUR FAVORITE CITY?
Oh, it’s impossible to choose a favorite. Too many amazing places in the world, and all for different reasons. I do find myself going back to Reykjavik, Iceland and Missoula, Montana quite often, though.
Favorite Airport?
SeaTac. Rocking chairs, free WiFi, mac n’ cheese, and outlets? Sold.
What’s your favorite city and airport?
Colin is right, ‘there are too many amazing places in the world.’ When it comes to potential favorite cities we’re spoiled for choice. But there’s a good chance that there’s one or two you find yourself going back to, no matter the reason. Let us know in the comments.
Cities aren’t just one thing. Each one is its own thing.
So maybe that’s why there was no consensus favorite among the digital nomads and pro travelers we asked. In fact, if there is a consensus, it’s that we’re not ready to settle on just one.
Read on for 14 digital nomads’ takes on their favorite cities and the airports that bridge between them.
DIGITAL NOMAD/TRAVELER PROFILE
Derek baron, wanderingearl.COM
Digital Nomad Derek Baron at the top of a mountain
WHAT’S YOUR FAVORITE CITY?
I don’t have one favorite above all others but I have a special connection with Melbourne, Australia. It’s where I studied abroad for a semester in university and it was that experience that opened my eyes to countries in Asia that I knew almost nothing about. This sparked my interest in travel and is the sole reason I went on my first solo backpacking trip to SE Asia back in 1999. I also have a lot of friends in Melbourne, I find it to be a beautiful city where it is very easy to meet people, it has endless activities and events, both in the city center and its surroundings and, to me, it just has a very appealing overall atmosphere.
Favorite airport?
Dubai, simply because it is the most diverse location on the planet and as a result, the single most fascinating place to partake in people-watching. Every corner of the globe seems to be represented in every terminal of that airport. It’s not always the easiest airport to fly in and out of or to change planes in but the people-watching opportunities more than make up for it!
DIGITAL NOMAD/TRAVELER PROFILE
James Clark, nomadicnotes.COM
Digital Nomad James Clark on sand dunes in the Sahara
WHAT’S YOUR FAVORITE CITY?
I nominate Saigon given I have spent the most time there over the last two years. It’s not everyone’s cup of tea, but I like my cities big and chaotic, and the street food scene there is among the best in the world.
FAVORITE AIRPORT?
Singapore Changi. It’s a comfortable place to overnight it and you can find reasonably-priced food (for an airport). It feels very homely (again, for an airport) with its warm carpet pattern and little nooks to chill out.
DIGITAL NOMAD/TRAVELER PROFILE
LIz Carlson, youngadventuress.COM
Digital Nomad Liz Carlson of Young Adventuress on the slopes
WHAT’S YOUR FAVORITE CITY?
New York. It has it all, and I never get tired exploring there. FAVORITE AIRPORT? Probably Queenstown here in New Zealand, mostly because it’s so small you only have to arrive 30 minutes before your flight departs, there is no security and you can park outside it on the main street, avoiding parking fees, and just walk in. When you fly out, you go over Lake Wakatipu and over the Remarkables, the local mountain range. So not only does it feel like you are getting a scenic flight whenever you take off and land, it also has to be the most convenient airport in New Zealand.
DIGITAL NOMAD/TRAVELER PROFILE
ROB HANLY, ROBHANLY.COM
Digital Nomad Rob Hanly poring over maps
WHAT’S YOUR FAVORITE CITY?
Berlin in Summer, Chiang Mai in Spring, and Medellin for the rest of the year.
FAVORITE AIRPORT?
Singapore, if only for their sleeping areas.
DIGITAL NOMAD/TRAVELER PROFILE
Conni biesalski, connibiesalski.COM
Digital Nomad Conni Biesalski sipping some fresh juice at a cafe
What’s your favorite city?
I don’t actually don’t have one. But if I had to name one, I guess it would be San Francisco.
Favorite airport?
Amsterdam Schiphol.
DIGITAL NOMAD/TRAVELER PROFILE
Amit Gupta, amitgupta.COM
Digital Nomad Amit Gupta rolling with his best friend
WHAT’S YOUR FAVORITE CITY?
My favorite city is one I’ve never been to. The first time I visit a place is always the most magical.
FAVORITE AIRPORT?
Singapore. There’s a free tour bus around Singapore if your layover is long enough. There’s tons of places to sleep or shower, multiple 24hr movie theaters, a rooftop pool, an orchid garden, a koi pond (two, actually). A butterfly garden! We did a layover here for our company Workcation to Thailand in 2013 and made a custom guide for everyone just because there was so much to do during the layover.
DIGITAL NOMAD/TRAVELER PROFILE
Clay Hebert, Clayhebert.COM
Digital Nomad Amit Gupta rolling with his best friend
What’s your favorite city?
I’ll always love New York City. Once you’ve survived in the belly of the beast, every other city looks like it’s moving at half speed. But that mandatory hustle can weigh on your soul and right now, San Diego is my favorite city in the U.S. It’s absolutely gorgeous here. The weather is consistently perfect. The people are laid back, and there is a burgeoning entrepreneurial scene. We’re surrounded by nature. We live with another couple in a 6BR house on 2 acres. We have a huge pool, a waterslide, a zipline and a treehouse that’s been featured on TV. Being in nature is part of the SoCal lifestyle, which is different than Manhattan, where you have to schedule an appointment with nature…(OK…I’m going to Central Park at 7am on Thursday.) Two weekends ago, we surfed in the morning and hiked a mountain in the afternoon. In the winter months, you could easily go surfing and snowboarding in the same day. Staying active is much easier here. Some of the top online marketers, podcasters and creators live here, and that’s not a coincidence. When you work online and can live anywhere, this is a pretty great choice. San Diego is perfect. Wait, don’t print that! I don’t want everyone to read that and move here. But please come visit!
FAVORITE AIRPORT?
In the U.S., I do love San Diego’s airport. It’s actually the busiest single-runway airport in the U.S. and second busiest in the world behind Gatwick, yet it feels small. Some gates are only a few yards from passenger pickup. Plus, it’s located right in downtown San Diego, so it’s not only convenient, but parts of downtown are like standing on the runway. It’s fun to look up and see planes landing every few minutes. In Europe, I like the Frankfurt airport. The clean and smart design is quintessentially German.
DIGITAL NOMAD/TRAVELER PROFILE
Mckel hill, nutritionstripped.COM
Digital Nomad Mckel Hill of Nutrition stripped chopping vegetables
WHAT’S YOUR FAVORITE CITY?
Hands down, Nashville! Although I have a hunch when I visit LA, the warm weather and health/wellness atmosphere will have me completely smitten.
Favorite airport?
Cincinnati, it reminds me of home.
DIGITAL NOMAD/TRAVELER PROFILE
Eytan levy, snarkynomad.COM
Digital Nomad Eytan Levy the Snarky Mountains in the mountains
What’s your favorite city?
Hmm…at this point, I’m not sure. A lot of my trips have been to relatively inexpensive countries, just for budget reasons, so I would have to visit some of the more modern cities in places like Western Europe to compare.
Favorite airport?
Every Asian airport I’ve ever flown through has been better than any Western equivalent. So much better.
DIGITAL NOMAD/TRAVELER PROFILE
Matt Long, Landlopers.COM
Digital Nomad Matt Long of Landlopers on the ice in a parka
WHAT’S YOUR FAVORITE CITY?
Paris, purely for emotional reasons. It was the first foreign city (not in Canada or Mexico) that I visited when I arrived as an exchange student in high school. It was a wonderful experience and further cemented what I always knew – that travel and learning about foreign cultures was what I wanted to do with my life.
Favorite airport?
Hong Kong, because I think that the Cathay Pacific lounges are the best in the world.
DIGITAL NOMAD/TRAVELER PROFILE
Kimberly Rich, theboldlifemovement.com
Digital Nomad Kimberly Rich of the Bold Life Movement in Iceland
WHAT’S YOUR FAVORITE CITY?
Tokyo and Rome come to mind for different reasons. Rome is undeniably romantic, and I love the history and the food it offers. Tokyo is unlike anywhere else, and truly embodies the appeal of travel for me. It’s so different from what I’m used to and would take decades to even scratch the surface.
Favorite airport?
LHR [London Heathrow]. I associate this airport with flying standby on my Dad’s former airline for last minute International trips. Even though it’s massive and hectic, it makes me feel spontaneous and cultured and truly alive.
DIGITAL NOMAD/TRAVELER PROFILE
Josh skaja, fretboardanatomy.COM
Nomadic Musician Josh Skaja of Fretboard Anatomy on stage-min
WHAT’S YOUR FAVORITE CITY?
I travel so much domestically that I don’t get to do as much international travel as I’d like, so this is heavily US-centric. I’m basically always on foot, and I’m mostly looking to eat great food and hear live music. I love me some New Orleans, Portland (Oregon), NYC and my hometown of Chicago. Raleigh, San Diego, and Austin great too.
FAVORITE AIRPORT?
I don’t know that I have one, so let me talk about the relative merits of the two Chicago airports. If you’re flying internationally, you don’t have much choice in the matter–you’ll be flying in and out of O’Hare. It’s busy, chaotic, and the traffic sucks. But badass chef Rick Bayless has two of his Tortas Frontera restaurants here, and that almost makes up for it. Terminals 1 and 3. If you’re going domestically, you’ll probably be a lot happier flying out of Midway–fewer delays, less traffic, shorter TSA lines. The food scene is less exciting, but it’s the airport where Southwest (my preferred airline) is. I’m basically always on foot, and I’m mostly looking to eat great food and hear live music. I love me some New Orleans, Portland (Oregon), NYC and my hometown of Chicago. Raleigh, San Diego, and Austin great too.
DIGITAL NOMAD/TRAVELER PROFILE
derek sivers, sivers.org
Derek Sivers on stage
WHAT’S YOUR FAVORITE CITY?
Depends on the need: New York when feeling super-ambitious, social, and connected. Los Angeles when feeling super- ambitious, but also needing silence and space for inward-focus, yet still being where things are happening. Singapore for the fascinating mix of people and outward-focus to the surrounding area. London for a perfect balance of all of the above.
Favorite airport?
Singapore, by far. I can’t think of any other airport I’ve ever really liked.
DIGITAL NOMAD/TRAVELER PROFILE
Colin wright, exilelifestyle.com
Digital Nomad Colin Wright of Exile Lifestyle speaking from the stage
WHAT’S YOUR FAVORITE CITY?
Oh, it’s impossible to choose a favorite. Too many amazing places in the world, and all for different reasons. I do find myself going back to Reykjavik, Iceland and Missoula, Montana quite often, though.
Favorite Airport?
SeaTac. Rocking chairs, free WiFi, mac n’ cheese, and outlets? Sold.
What’s your favorite city and airport?
Colin is right, ‘there are too many amazing places in the world.’ When it comes to potential favorite cities we’re spoiled for choice. But there’s a good chance that there’s one or two you find yourself going back to, no matter the reason. Let us know in the comments.
