Stories from Digital Nomads

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…

I’ve been traveling for close to twenty years. In that time, the airline industry has changed a lot. The use of points and miles has become widespread, round-the-world tickets have gone the way of the dodo, airlines have consolidated, and there has been an explosion of budget airlines. Over the last few years, the cost of airline tickets has steadily risen. They get more and more expensive while their prices often seem illogical. Since ticket pricing is an arcane and misunderstood subject, I want to take some time to explain why your airplane ticket costs what it does. A Look at the Airline Industry Ticket prices have increased over the decade for several reasons. For …

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…

Travelers can be a fickle group of people to buy gifts for. We’re constantly coming and going, we usually don’t carry a lot of stuff with us, and no two travelers are alike. Finding the perfect gift for the traveler in your life can be tricky. While a plane ticket is never a bad idea (I’m a window seat in case anyone is thinking of getting me one), I’ve put together this ultimate gift guide for travelers as there’s a lot of great travel gear out there these days that helps people travel cheaper and better. Even me, the gear-adverse traveler, likes a lot of this stuff! This is stuff I actually think is super useful. No nonsense. No fluff. Just the best gifts for intrepi…

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…

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 …

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 love road trips. You get in car and can just head off anywhere you want. There’s a freedom to a road trip that you can’t get with trains (and, don’t get me wrong, I love train travel too). Small towns, beautiful parks, historic buildings….whatever you see, you can stop for and can stay as little or as long as you’d like! Over the years, I’ve been on dozens of road trips. Some destinations are just meant for them (think New Zealand, Ireland, Iceland, the United States, South Africa, etc, etc.). However, when you don’t have your own car, renting one can be a pain in the ass. No one likes doing it and we all (rightly) worry we’re getting ripped off. There’s always a lot…

There’s a lot of tours in New York City (I’ve highlighted my favorites here) but I think one thing people don’t do enough of is Airbnb experience. Most of us know Airbnb through their stay features but they also have a lot of experiences where you can get a local to show you around. I actually like these experiences more than traditional tours because they have locals who share something they are passionate about, they are small groups, and they are usually a bit more off the beaten path. I don’t think people take these tours enough and they are always one of my favorite things to look for whenever I travel anywhere in the world. New York City has a ton of options you ca…

There’s a lot of walking tour companies in Paris. I’ve taken hundreds (I’ve reviewed my favorite tour companies in this post). Besides formal tours, there’s another thing I love to do in Paris: Airbnb Experiences. Airbnb Experiences are like the holy grail of tours: they are unique, off-the-beaten path, and run by locals who just want to share something they love. They aren’t cookie cutter walking tours or activities lead by a guide holding an umbrella. I absolutely love Airbnb Experiences. They are one of my favorite things to do in any city and, frankly, I don’t think nearly enough travelers do them. Whenever I run polls about them, half usually say they have never he…

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…

Spain has long been associated with sun-drenched beaches, vibrant cities, and world-famous cuisine. While Barcelona, Madrid, and Ibiza are famous for a reason, the true soul of Spain is often found in its remote corners. One of the areas I love the best is Northern Spain, with its green mountains, rugged coastline, and medieval villages, offers an entirely different perspective. It doesn’t get as many visitors as the hotspots in the south but it is just as beautiful in my opinion. If you want to see a quieter side of Spain, consider stepping off the usual tourist trail and heading north after your flight to Madrid. Spend a few days in Madrid (which is amazing) and then t…

There’s nothing like Sweden in the summer. Light hangs in the air for hours, boats nose through island-studded bays, and cafés spill onto sidewalks as Swedes take advantage of the fleeting warm weather. With so much of the year spent in the cold and dark, the never-ending light that summer brings does not go to waste. Whether it’s on the many islands that dot the country’s coast, at their rustic cabins in the woods, or lounging in the city parks, Swedes flock outdoors. I’ve been to Sweden many times (including spending an entire summer in Stockholm) but have always focused on the southern part of the country. However, with a desire to see something different this visit…

This is a guest post by Raimee Iacofano from Raimeetravel. Growing up in Michigan, Ludington was THE place to be. Every summer, my family would pack up the car, blast some classic rock (think Tom Petty, Fleetwood Mac, and the occasional Lynyrd Skynyrd singalong), and head west for beach days, lighthouse climbs, and the BEST Superman ice cream you’ll ever have. It was tradition for us each year because my grandparents called Ludington home. As a kid, it felt like pure magic. Falling asleep to the sound of waves, chasing seagulls barefoot in the sand, and sticky fingers from melting cones that somehow always dripped down to my elbow. Ludington wasn’t just a vacation spot …

Ruin bars are all the rage in Budapest and have been around since the founding of Szimpla Kert, the mecca of all ruin bars, in 2002. These bars are built in Budapest’s old District VII neighborhood (the old Jewish quarter) in the ruins of abandoned buildings, stores, or lots. This neighborhood was left to decay after World War II, so it was a perfect place to develop an underground bar scene. These places were very off the beaten path, rough around the edges, and catered to artists, students, and alternative people. But they became very popular and well known by 2010 and have nice gone mainstream, though their setting has not changed. From the outside, these bars look …

Terms apply to American Express benefits and offers. Enrollment may be required for select American Express benefits and offers. Visit americanexpress.com to learn more. If you fly Delta frequently and want to earn toward elite status while enjoying more travel perks than their Gold card offers but don’t want to pay the high fee of the Reserve, the Delta SkyMiles® Platinum American Express Card is likely the best fit for you. It’s a step up in both annual fee and benefits, giving you tools to reach Medallion status faster, plus credits that can offset travel costs. Here’s my review of the card! Delta SkyMiles® Platinum American Express Card Overview The Delta SkyMile…

Terms apply to American Express benefits and offers. Enrollment may be required for select American Express benefits and offers. Visit americanexpress.com to learn more. If you fly a few times a year, you know the pain points: baggage fees that add up quickly, boarding last and finding no overhead bin space left, and earning miles at a snail’s pace. That’s where the Delta SkyMiles® Gold American Express Card can really change your travel experience. I’m a believer that if you fly one airline at least a few times per year (or have a favorite airline), you should at least get the airline’s lowest tier credit card as it comes with enough perks to justify the cost and will m…

Terms apply to American Express benefits and offers. Enrollment may be required for select American Express benefits and offers. Visit americanexpress.com to learn more. For Delta loyalists who want a VIP experience, the Delta SkyMiles® Reserve American Express Card is your best option. I’m a huge fan of Delta and I fly them almost exclusively when I’m traveling around the United States. I find them to have the best in-flight experience, food, entertainment, and seats. If you’re a Delta fan and fly them a lot, then I really think the Reserve card is must to have. While it has the highest annual fee, it also has most comprehensive set of benefits, including Sky Club acc…

From sea to shining sea, the United States is a very diverse country – both when it comes to culture and natural beauty. I’ve traveled across the continental United States many times over (you never really realize how big Texas is until you drive through it. Damn that state is big!). I think, just on my roadtrips alone, I’ve spent a collective two years exploring the country. That’s a lot of time and doesn’t even take into account that visit to Portland or Nashville or weekend in Savannah. In short, I’ve seen a lot of this country. And there is a lot worth seeing. In the past, I’ve talked about my favorite restaurants and lessons learned, so it only seems proper to g…

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. …

Advertiser Disclosure Terms apply to American Express benefits and offers. Enrollment may be required for select American Express benefits and offers. Visit americanexpress.com to learn more. The Platinum Card® from American Express is the OG of premium travel cards. Since its launch in the 1980s, it’s always been known for its exclusivity, suite of perks, and stellar customer service. While it does have the highest fee in the game ($695, See Rates and Fees), it offers a ton of bang for your buck. You’ll more than come out on top if you take advantage of all that this premium card has to offer. It unlocks the most comprehensive lounge access of any card, includes elite …

Advertiser Disclosure Terms apply to American Express benefits and offers. Enrollment may be required for select American Express benefits and offers. Visit americanexpress.com to learn more. Over the past nineteen years as a business owner, I’ve used countless business cards. Some have been amazing and elevated both my travel and my business. Others have been…well, lackluster. One of the best? The Business Platinum Card® from American Express. It comes with a lot of world-class perks and benefits, quality customer care, and a solid rewards structure (especially on large purchases). While the annual fee is pretty high ($695, pay over time available. See Rates and Fees…

Travel has become really expensive. Post-COVID, the entire world seems to be traveling again and prices just keep rising. I am astonished at how high they have gotten. But it’s a product of rising costs and out-of-control demand. Everyone just wants to travel. We’re all looking for an escape. Fortunately, it’s not all bad. Airfare has started to go down again, there are more deal-finding websites online, free walking tours in more cities, and more opportunities to bypass the traditional travel infrastructure and connect directly into the local way of life via the sharing economy. As we navigate the post-COVID world of high prices, I want to share some tips and tricks on…

I’m a big fan of Daily Drop. It’s a points, miles, travel, and credit card newsletter created by my friends, Kara and Nate (they run a big YouTube channel of the same name). Daily Drop keeps you informed about the latest news and information around points & miles, as well as updates across the airline and hotel industries. While the newsletter is free, they also have a subscription service called Daily Drop Pro, which promises even more points deals, alerts, and tools to help you find the award availability you need for your next trip. But does it deliver? Is it worth the price? As Daily Drop has gotten bigger, I’ve gotten questions about the service from readers …

Most people aren’t born savvy travelers. It’s something that only comes with on-the-road experience. Travel savviness is a process born of missed buses, foolish behavior, cultural unawareness, and countless tiny errors. Then, one day, you begin to seamlessly move through airports and integrate yourself into new cultures like a fish to water. In the beginning, you’ll make a lot of travel mistakes.But I want to help speed up the process and help you avoid my mistakes (and I often make a lot of them), so I put together this giant list of my best travel tips that cover everything under the sun to help you reach your full travel ninja potential. I’ve learned these tips over …