Digital Nomad Travel Tips

Traveling the world for months, seeing wonders and experiencing the mosaic of global culture, the digital nomad life is amazing yet challenging. It is a both old and new: new in that we can still remain so closely connected to work and job at home while being far away, yet quite old in that travelers have been doing much the same, without the instant connection back home, for thousands of years. I am sharing here my tips from my travels to about thirty countries covering over two years of time in foreign lands, plus a good number of months on the road back in the US as well. I am not going to put much effort into selling this lifestyle to you, it mostly sells itself: beautiful and awe inspiring sights mixed with challenges, the new, and the unusual. It is fun and leaves great memories, but especially (and more so than other, more packaged or shorter forms of travel) can do a lot for helping one learn and develop as a person. Here, though, are some thoughts on managing the challenges this life can bring.

My experience is on working remotely while traveling, usually alone, normally for 1 to 3 months, mixing in a few long weekends of intensive sightseeing along the way. I think the key to the success of these trips is three fold.

One is maintaining a sense of balance: balancing work with play, busy with relaxing, short with long term, home with travel. You can’t see this just as a holiday nor just as a new working location, but a blend and alternation between those. You will regret it, coming home after six months, if you haven’t talked to your old friends nor kept up your career at all during that time. You will also regret it if you spend all day inside working and never seeing any sights or make new friends.

The second is preparing for problems. Something always goes wrong. Flights get delayed. A war starts. You get sick or injured. Clouds and rain ruin the excursion you were most excited for. Being mentally prepared for these and having the flexibility to adjust is really important for the having a good overall experience (and you know, not dying).

Thirdly, finding friends and people to socialize with. The number one secret to happiness in traveling is meeting people. Some will be other travelers. Some will be chatty locals. Some will be commercial contacts like a good tour guide. Most reliable are the street cats. Easily bribed with snacks to be friendly, and don’t waste too much time chatting. Socializing is often the hardest part, but brings much of the joy.

We can get back to these groups in more details, but let us start with the basics.

The Basics, Assorted Advice

Your ideal trip minimum is one month. One month = cheaper rentals (in most places). Since you are working at the same time, one month means enough weekends and evenings to see many things. Three months is probably the max you will stay in one place. For one thing, three months is the max of most tourist visas (although 2 year nomad visas are getting more common). I also have an environmental component in my thinking: if you are throwing all the carbon emissions out for a long plane flight, you should use it for as long as possible!

I am pretty obsessive about double checking that I have a working phone, with a charged battery, money available, and an ID available at all times. My Google Fi phone plan works in most countries but without that, most people end up buying a local sim card to get local data. You will use your phone a lot, which means the battery will get low. A charger or extra battery is usually critical. Google Maps (download offline maps) + Google Translate (download offline language) + Google Lens (to read the signs) are life savers in all sorts of situations. These services are also often a bit wrong, so don’t follow their advice blindly. If you lose your passport, life gets miserable. Also, expect to have your credit card either stolen, lost, or blocked (because your bank thinks all your new weird purchases are fraud). I usually have $100 or so worth of cash (both US and local currency) for emergencies, plus a backup bank card from a different bank stored in a separate location. Avoid the touristy ATMs, they have horrible fees, usually ATMs from a major local bank are best.

I am generally assuming you have enough money for this trip. Traveling on the very cheap is more stressful. More money generally means more fun. Also, remember that something will go wrong statement? Often times you can pay your way out of difficulties, so plan to have a slush fund for that. If money is short, your main solution is finding cheap places to go. Housing and flights will be your main expenses and those are pretty easy to look up in advance. There are people who can give advice on saving your pennies, but that really isn’t my way, sorry.

Location, location, location!
Wherever you go, your housing selection can really determine the quality of your stay. It is really nice to have a walkable location where you can take a walk to a grocery store and some restaurants. For me, it is also important that the neighborhood be good for cycling and running. It doesn’t have to be right next to the all the cool things, however, just have a way of reaching them. Where you stay ideally should have laundry, a kitchen, internet, and a table or desk to use your computer at. I think it is really important to have a safe, relaxing personal space available – which is why, while staying at busy hostels can be a lot of fun, I would never do it for more than a few days.

I think the most time consuming thing I research while I travel is transportation (how do I get to the cool things?), so the more transit options you have nearby (walk, bike, bus, train, ride hailing app, car rental, etc.), the lower stress your travel will be. I recommend knowing before you leave ways to get to where you are staying from the airport, since most likely you will be exhausted and struggling and just want to sleep. This includes tickets/apps you might need. It might be stating the obvious, but things like hailing a taxi differ, not everywhere has good Uber service (Bolt is a common alternative, etc). Food delivery apps especially vary by region. You can often “make it up as you go along”, no need to research every little detail, but research does go a long way to making the experience more relaxing.

The USB-C charging standard is a packing saver and helps prevent having a spider’s web of cords in your bag. Get all your electronics using this type of plug for charging and then get a slimmer but high wattage (GaN) charger with international swappable heads. But don’t spend lots of money on this if you don’t have it already. Generally you can travel just fine without buying any new accessories. I do like bringing a computer mouse and a lightweight laptop stand, but generally you don’t need to buy all the portable monitors and fancy electronics hubs. Good internet is more important than anything else. Local sim card in a hotspot might sometimes be necessary.

I personally don’t like working in cafes or coworking spaces that much. You don’t get much socializing done (since you have to work) and you end up wasting time being less productive due to all the distractions. I like working from my airbnb and doing the fun stuff elsewhere. It works for me, but perhaps you will be different.

Getting sick is miserable. Foreign hospitals are confusing and not really designed for tourists. What is available at the pharmacy often has a different name. Always travel with some basic medicines. Being sick really makes you want to go home. Sometimes you should just head home, other times it is worth pushing through and staying.

Language: learn the basics of the local language. “Thank you”, “Good morning” and “please” are just about all you need. Learning the full local language is impossible without years of hard work, but a few of the most basic phrases, learned well and used, convey some basic respect. The people working at stores may not speak English, but usually the process is so obvious you can communicate without speaking the same language. Many people speak surprisingly good English.

Packing is a difficult Goldilocks situation. Minimalism is best in theory but on longer trips it is good to be prepared for mixed weather, to bring some basic comforts, and have more than one change of clothes. But also don’t pack too much and really make sure to only bring what you will use because a big suitcase is a pain to carry around. You can buy a lot of things you will need (shampoo, toothpaste) in your destination, but it is often nice to have at least a day or two worth to get started with, so you can sleep when you arrive, rather than immediately go shopping. Also plan for space for souvenirs coming back home.

Pro tip: observe the locals. Watch how they buy fruit, for example, do they weigh it at a machine, or just grab and go? When they get on the bus, how do they pay and what door do they get in and what door do they come out of? A lot of awkwardness can be avoided by careful copying of the locals. But also don’t be afraid to ask for help and play up the “I’m a stupid tourist” act when needed, it is sometimes helpful too.

Actually, observing the locals and why and how they do things is one of the reasons to travel. It makes you question and think about the basics of your own life.

Where to Go

People often worry most about where to go, but I have good memories from everywhere I have been. What really makes a trip bad is when things go wrong, so probably the one main advantage to visiting a more similar western country (like England) is that it can be easier to understand and fix problems there (one commenter has other ideas: “highly disagree. bad decisions make the best stories”, so you do you). Probably the rule of thumb is that countries that have had a coup or civil war in the last two decades or so are countries you should wait to visit until you are a bit more experienced a traveler. The only places you really need to avoid are anywhere that might want to take you hostage just for fun: currently Iran, Russia, and North Korea are top of the avoid list, or that actively jail people of your identity (like some countries do with LGBTQ people).

In the unlikely event you are struggling to find a place to go, follow your passions. Do you like certain ethnic foods? Go to a place known for that food. Do you like hiking in mountains? Find some mountains. Do you like sword swinging fantasy? Find a good castle. But not all passion has to be preexisting. You can build up passion by watching some videos about the country or movies filmed there.

Different is good! I am often much more disappointed by traveling in the US than I am in a foreign country. I mean, I still have lots of fun because parts of the US are amazing, but the stores, the signs, the people, are all very similar here so it is missing much of the depth of traveling in a foreign culture brings.

I often recommend planning to visit at least two distinct places, ideally somehow connected (one on the way to the other). Especially in Europe where countries are so close together there is little reason not to cross a border to see what is on the other side. But don’t try to visit all of Europe in one go, too many places and you end up not being able to appreciate them. I really enjoyed the thirty day pre-packaged but self-guided car tour of New Zealand I did with my parents, but that sort of constant movement doesn’t work well with working remotely, tends to be expensive, and doesn’t build as many long term connections.

Big cities have lots to do. Cities like London, Paris, and Rome are famous for a reason. They are usually the safest choices. But some of my best experiences come from visiting smaller towns and less touristy areas. Small towns, people actually can get less annoyed by foreigners (unlike big cities, where they can get overwhelmed) but also they are less likely to speak English or have easy to use infrastructure.

I will say that places where you can go car-free, or only need to rent a car for a short weekend side trip, are generally better and cheaper. Another advantage bigger cities tend to have is having more transit options.

If you are having meetings in a different time zone, plan that out in advance. Flying to Europe from the US works pretty well. It means I have meetings in the evenings there (no Friday night partying) but I don’t mind that. South America is more of less the same time zone as the US. For Europeans, the same shift applies for going to Asia (Thailand, etc) which is why you see them going there so often. Asia doesn’t work so well for US digital nomads, although I have heard there are places (Philippines, India) where there are so many off-sourced workers working US time that parts of the city are alive all night to support them.

Avoid places that are very touristy during peak tourist season. Sometimes it might be worth going during a busy time (like for tulip blossoms in Holland in spring), but generally think twice about it.

People know to avoid cold and rain, but traveling in heat can be even more miserable. You can look at average monthly weather for a place in advance to get a feel for what it will be like there. You need to know yourself: will you be able to enjoy yourself in bad weather? Some people can, and some people struggle with it. Preparation is key, bring the right clothes.

I have observed among travelers that trip satisfaction and prior expectation are very closely linked. For example: a lot of people go to Budapest not expecting much, then give great reviews about visiting it because it beat expectations. However, I had heard a lot of amazing comments from other travelers about it before visiting, and I was rather disappointed after. It was perfectly nice, but didn’t in my mind meet the hype, and failed to meet expectations. This is part of the reason I am focusing on problems and difficulties here: you need to set realistic expectations or else you may be disappointed, even if your trip was generally good overall.

One thing I will say is that you will feel bad at some point on a longer trip. Sometimes it happens right at the beginning, when I’m exhausted by flying in a foreign land where I don’t know anything and all I am doing is spending money trying to keep everything from falling apart. It always happens when I get sick when traveling. Being lonely can set in after a few days, especially if you see photos of your friends or family doing fun stuff back home. Expect to struggle a bit. Sometimes you should go home early, but usually you can push through these feelings with a little work. And that solution, usually, is socializing!

You should plan your trip around socializing options. Here are some ideas:

  • Staying at a hostel. Always stay at the more expensive ones, the cheap ones can be a disaster. Expect there to be poor sleep, people doing stupid things, but also tons of fun. Good for a few days, without too much luggage. Plenty of older folk come through but the majority are young.
  • Staying at a coliving space. These are newer and less common than hostels. Basically hostels for older people with more money. I define them as everyone having private rooms, and usually a quieter atmosphere, with dedicated spaces for remote work. Usually expect people to stay two weeks or more. Highly recommended! Do note there are some ‘coliving’ communities that are actually more like housing associations of permanent residents, which are not what I am talking about.
  • Local group activities with a shared passion. For me, this is cycling. It’s pretty easy to fit into a local group ride with others and learn a lot from them about the local place. I do think specific “meetups” can be kinda awkward, so I recommend more organic groups. Shared passions and interests always lead to a better connection, rather than just meeting up to meetup.
  • Dating apps: I am a bit embarrassed to say it, but I actually have made some great friends via this approach. This can be a high stress, high failure rate approach, so expect some emotional damage. I feel like this tends to go poorly if you are going into this already feeling lonely, and the other approaches are actually better for helping with loneliness.
  • Tour Package: I dislike ‘packaged’ vacations, so I would tend to avoid doing an entire trip that is a tour group, but for some people that works very well, especially if they all share a general passion (like a hiking focused group, etc). Those types of vacation also tend to be overly expensive and too distant from local culture. But the socialization is built in, so often these trips are a safe bet. Do some research and looks for groups that will bring together like minded people rather just a generic cruise.
  • Tour Groups, specifically smaller and shorter tours, like day trips, are definitely great and an easier option to recommend than a package tour. I have had better experience with small group, specialized tours (Modena food tour in Italy, coffee tour in Colombia, bush plane flight in New Zealand), but some people swear by the generic free walking tours available in most cities. The tour guides will often answer a lot of your general local questions too, if you were too afraid to ask elsewhere (how do I use the bus?), and sometimes you can make friends of other travelers on these. The structure of these is great when you are still trying to figure all the local systems out, so often they are useful near the beginning of a longer trip.
  • Meet with friends midway: if you have made friends from past trips, or have friends from back home, or online friends you have never seen in person, meeting them as part of a trip is always nice. I feel that traveling with a friend can be frustrating unless you are very good friends who get along very well. I also feel that traveling alone is better for self development. The solution is to travel with your friends just a bit. Meet them along the way, travel with them for a weekend, but don’t do it for the whole trip. It is easier to coordinate and is almost always great fun.

Overall: for socializing, it is much easier to make friends with other travelers than it is with locals. And it is easier to make friends with locals who have more in common with you. Often small towns can be more isolating than bigger cities. Pro tip: meet fellow travelers from other places and then later go visit them at their home town (with permission and their welcome, of course). That’s an easier way to get an introduction to a local community!

Concluding Advice

Embrace the awkwardness of not speaking the language. The awkward “how do I tell them I have no idea what they just said”?
Embrace the awkwardness of eating alone and being alone in a giant room full of people who occasionally glance at that weirdo in the corner.
Embrace the awkwardness of having no idea what you are doing (like getting on a bus) in front of a crowd of people who have known how to do it since they were about 2 years old.
Yes, there is a lot of awkwardness when traveling to a foreign land. But you mostly forget about it and the good memories remain, so just be respectful to others and don’t let it bother you too much.
(actually I used to be much more introverted and awkward, but all my travel has helped me to stop worrying so much about the little social things. Now I am gleefully awkward)

Embrace the every day of activities like grocery shopping in a new country. There’s a lot to appreciate in a foreign supermarket if you pay attention to the detail! I feel like it is the little things that often provoke big thoughts, and longer trips have more time to let those ideas grow.

I personally believe most employers these days can allow at least some time out of office. Talk them into letting you be gone for a month or two, mix in some holiday, and make your life a lot more enriching.

Traveling won’t solve your problems, but it does add perspective and bring joy. Go plan your next trip now!

Leave a Comment

Your email address will not be published. Required fields are marked *