Stories from Digital Nomads

I love walking tours. Long time readers know I always recommend doing them first thing when you’re in a city. It doesn’t matter the type you do. Food, history, art – whatever! Just do something. They’re an incredible way to learn about a destination, get your bearings, and talk to a local about life in the city. (Plus, you can ask your local guidefor tips on restaurants, attractions, or how to navigate the city! Win-win!) I’ve been taking walking tours since my first backpacking trip in 2006 when I joined a hostel’s free walking tour around Prague. I was hooked and, over the years, I’ve taken hundreds upon hundreds of tours run by dozens upon dozens of companies. There a…

I used to think “home” was a dirty word. Out there — on the road — was where life happened, full of exciting adventures, fascinating people, and endless possibilities. No dreary commutes, 30-minute lunch breaks, mind-numbing meetings, or endless lists of to-dos squeezed into a rushed weekend. Why would anyone want to be home, the place where routine seemed to sap your will to exist? It baffled me. My first trip overseas — a vacation to Costa Rica — made me fall in love with travel. For all the reasons mentioned above, I realized why “vacations” were so romanticized in work culture. There was a freedom to them that stood in stark contrast to the daily corporate grind. …

When you’re traveling, staying connected is essential. Whether you’re figuring out the best route to your hostel, finding a place to eat, or translating a train schedule or menu, having reliable data makes life on the road infinitely easier. I still remember my early days of travel carrying a physical guidebook around as I wandered the streets looking for my accommodation. Or, when smartphones became widespread, searching for a SIM card kiosk to buy a physical SIM, trying to poorly communicate with staff in a language I didn’t know, and spending 20 minutes swapping out tiny plastic chips. Luckily, things have changed and life is incredibly easier thanks to eSIMs. Rather…

I used to hate renting apartments from websites like Airbnb or VRBO. As a solo traveler, I preferred the social atmosphere of hostels. You met people, hostels ran activities and they were where you were “supposed to stay” as a backpacker. When I did want something other than a hostel, I used a hospitality network liked Couchsurfing or simply stayed with friends. But, after close to two decades as a nomad, there are times when I like my privacy and the ability to “create a home.” I like to cook, want to relax on a couch, and just chill. While apartment rentals often contribute to overtourism (discussed more below), there are still plenty of real hosts out there who are…

I’m a sucker for a good travel rewards card. Over the years, I’ve collected a small handful of them — not because I love juggling annual fees, but because the right cards can save you a lot of money on flights, hotels, and travel perks you’d otherwise pay out of pocket for. Not only do I have a bunch for my personal expenses but I have a couple for this business too. One of my favorite business credit cards is the Capital One Venture X Business Credit Card. It’s Capital One’s top-tier business product. I love it because there’s a big welcome offer, lounge access to over 1,300 airport lounges, annual travel credits, and a simple 2x reward on all spending (which ensures yo…

Years ago, the website Earth Porm reposted my article “The Ultimate Guide to Traveling When You’re Broke.” As I went through the comments on the post, I was dismayed by the mean and dismissive comments people shared as well their misconceptions about travel. These comments made me realize that, despite all the detailed websites and books on how to make travel affordable and accessible, too many people still believe the notion that travel is expensive, unsafe, and impossible unless you are rich. Too many say, “I can’t. It’s impossible” and become cynical about travel. The notion that travel is expensive couldn’t be further from the truth (I wrote an entire book proving …

Tokyo is one of those cities that feels endlessly deep. You can visit a dozen times and still discover new food stalls, hidden shrines, late-night bars, quirky subcultures, and neighborhoods that feel like completely different worlds. (I know because I’ve visited about 10 times already!) One of my favorite ways to explore Tokyo is by taking an Airbnb Experience. Led by locals and long-term residents, these tours give you a front-row seat to Tokyo’s food culture, nightlife, history, and crafts in a way you rarely get when wandering on your own. I’ve done a lot of Airbnb Experiences in Tokyo over the years and think they are often even better than traditional tours you fin…