5 travel tips for digital nomads and perpetual travelers

Written by Andrew Henderson

Dateline: Milestii Mici, Moldova

Chances are, you’ve never heard of Moldovan wine. Perhaps you’ve never even heard of Moldova.

Yet here, 30 minutes from the capital city of this tiny former Soviet nation are some truly excellent wineries. In fact, the largest wine cellar in the entire world is right here in the village of Milestii Mici. The place even has a “National Wine Day”.

For all of about 6 euros, I purchased a rather good bottle of Muscat. They also have an excellent dessert wine where you can really taste the strawberries. To me, this is just further proof that being a nomad is about finding the best opportunities of all kinds, even when it comes to daily indulgences such as wine.

Go where you’re treated best.

Owing to that philosophy, running an offshore business while traveling the world is increasingly common. Sites like this have inspired thousands of people to join a revolution as perpetual travelers and digital nomads.

I’ve been a perpetual traveler for years and I’ve learned a lot of lessons along the way. Here are a few of them:

1. Don’t be dogmatic

Comedian Adam Carolla has a joke about restaurants selling “their version” of a club sandwich, using that as license to make the sandwich practically indistinguishable from the international standard most of us are used to.

While people doing things “their way” can be frustrated to those of us who were told “the American way is best”, you’ll have to learn to adapt if you want to survive overseas. (Or, be ready to pay through the nose for your version of service.)

The best piece of advice I was ever given when it comes to living or doing business in emerging countries.

Chances are you won’t be as familiar with the way things are done in these countries. I do believe that things like hospitality standards will rise over time in some countries, but you need to accept that things may be different elsewhere.

It’s amusing to hear US persons complain of illegal immigrants who won’t adapt to the American way of life then go overseas and complain that restaurants in Laos don’t serve free tap water.

2. Don’t think everything is (or should be) dirt cheap

I recently had a dentist in Romania examine and clean my teeth. The bill came to $70. Not ridiculously expensive, but not cheap. I know guys in the United States who spend $1,000 taking their three kids to the dentist every six months, but somehow think it should cost $13 in Romania.

The simple premise behind this lesson is that, chances are your country isn’t #1 in whatever it is you expect to be cheaper elsewhere. Plenty of US dentists are using antiquated technology because it’s so expensive to replace there, while Romanian dental clinics are state-of-the-art.

Top quality is top quality anywhere. In fact, the poorer the country, the more expensive top quality often is. As I always say, Rolex doesn’t sell its watches at lower prices to Cambodians just because most of them are poor.

Being a perpetual traveler has been made out to be the ultimate in cost savings by some. And it’s true you can bootstrap a business in places like Asia, but the chief reason for applying flag theory is personal and financial freedom, not $1 Thai lunches.

3. Use frequent flier and frequent traveler programs

If you’re from North America, chances are you’ll find traveling much more civilized in the rest of the world. While Delta and United cry poverty as an excuse to slash free trail mix, even low-cost airlines in Asia and parts of Europe are still serving free meals on short flights.

That said, no matter where you travel, it’s always a good idea to have special perks for your airline or hotel chain of choice. The most important of these is a good frequent flier program.

I’ve personally accumulated millions of frequent flier miles over the years, both through travel and heavy use of credit cards. Once you figure out your main travel routes, choose an airline that works with your plans and sign up for their frequent flier program.

Middle Eastern airlines are some of my favorite right now. Emirates is perhaps the best airline on earth, even if their miles aren’t redeemable on many other carriers.

I personally love Qatar Airways since Doha is a great stopover on my Europe-to-Asia flights, and Qatar’s partnership with the Oneworld alliance means I can earn and redeem miles with Cathay Pacific, British Airways, Finnair, and others in case flying Qatar doesn’t make sense for a certain flight.

4. Don’t cheap it out

Every time I turn around, there are 11 new blogs about “how to travel on the cheap”. I don’t begrudge people telling their story of how they quit their job and traveled, but if you’re a digital nomad running a business, “cheap” may not be what you want.

In Malaysia, for example, Malaysian Airlines is often only a few dollars more expensive than discount carrier AirAsia. Compared to a lot of airlines, AirAsia is far from bad, but Malaysian has excellent service and often offers first-class upgrades for as little as $75 more, not to mention free baggage.

In other words, don’t become obsessed with how to save $9 only to make your life miserable.

Similarly, even though you COULD eat for $6 a day in some places, that might not be the most productive. I feel energized and happy when I eat at bright, cheerful restaurants with pleasant staff.

If paying $15 for lunch in a country like Romania is the price of me being productive, that’s a price worth paying versus cheaping it out at some smoke-filled dump that makes me miserable and frustrated.

5. Consider a home base (or two… or three)

Last summer, I reported that I had set up a home base in Kuala Lumpur, Malaysia. KL is a fantastic city – the most livable in the region short of spending a fortune – and it’s nice to have a base of operations to get some serious work done.

When you’re traveling non-stop, you are always going from appointment to appointment. You’re constantly looking for a dry cleaner or a cobbler or a shoe shine place. And you’re constantly feeling that you need to be out and about.

Having a base eliminates these issues and allows you to get work done. Otherwise, life feels like a perpetual vacation that you have to interrupt with necessary work. There’s nothing wrong with that, but it can also feel a bit odd.

Having a base in a country that doesn’t put you at risk of paying taxes there is a great way to have a place to store extra clothing and keep the organized part of your life. I’ll write more ideas for setting up your own base soon.

What strategies, tips, or tricks have you developed as a digital nomad or PT? Leave a comment below.

Andrew Henderson
Last updated: Jun 22, 2020 at 10:06AM

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  1. ichi

    Excellent article. The biggest question that I have about setting up a home base, is how to get around the tourist visa restrictions, which oftentimes seemed to be only good for 30 days. It would be awesome if you could address that question in future articles, Andrew. Thank you.

    • Nomad Capitalist

      Thanks. Some of those countries offer easy tourist visa extensions. Otherwise, it would be best to use longer tourist visas or residency programs that don’t tax worldwide income.

  2. PeacefulLife

    Well written. I get my teeth cleaned in BKK for around $30USD and buy great clothes in Slovakia for half the US price. Not a big shopper but just the basics. Take residence for $60/month all EU medical coverage and a 15 year drivers license. Can fly F class on CX, JL or QR buying miles (over now) with USAirways. Flown F class on 10 different carriers and never paid more than $2500US for these LHaul flights. Have invested 5 years understanding and dealing with MOI re citizenship in SVK, Hungary and CZ Rep. Loopholes are tightening and even descent rules can be BS these days with requesting endless paperwork and language tests that locals couldn’t pass. Read, learn and take a chance but enjoy the ride along the way.
    Blava SVK

      • PeacefulLife

        Great when they allowed you to buy miles.

  3. bill mann

    Andrew, the part of this article about cheaping out really stood out to me. I know too many expats with guaranteed pensions, or more income than they know what to do with, but are still focused on where’s the cheapest beer, or where can they save 10 cents on an almuerzo, quality of quality of food, or beer, or experience be damned. You are right that emphasizing what makes you happier and more productive, rather than what’s cheapest, is the way to go.

    • Nomad Capitalist

      I have learned over the years that having an abundance mindset is better for business and for quality of life. It’s why we decided to help people accomplish various offshore tasks ourselves: people like me just want a result, not to know how sausage is made.


    I hold a Salvadorean passport with access to 135 Countries and territories with no visa need. Currently in Manaus AmazonaS Brazil . I came through Colombia to Leticia by plane,then by Ferry 3,5 days sleeping in a hammock down the river . It is amazing.


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