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How to Plan Long-Term Remote Work Trips

digital nomad travel checklist
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So you’ve got the skills you need to get a remote job, applied to remote job listings, and signed your offer letter. Congratulations!

There are tons of reasons why people might want to go remote—the flexibility, needing to stay home with kids, working in pajamas—you name it! But you picked remote life for one reason and one reason only: the opportunity to travel.

But even if you’ve done a lot of traveling before, living the digital nomad life is a completely different experience. You will no longer just be a traveler. Travel will be your life.

I honestly had no idea what to expect when my partner and I left Australia to travel the world in 2013. I was equal parts scared and excited. Looking back, I definitely wasn’t ready. I had no idea how to work and travel at the same time. I was disorganized and didn’t quite know how to set myself up for productivity in a new place.

But of course, I learned my lessons by diving into the deep end, and today I want to share some advice on how to plan your first digital nomad trip.

If you’re already an experienced traveler, you might be thinking that you don’t need travel planning advice, thank you very much. But planning a digital nomad kind of trip—one where you’re essentially living on your trip instead of just vacationing—does have a few unique considerations. So, even if you’ve done this a million times before, here’s everything you need to keep in mind.

Getting Your Visa

Visas are a complicated and thorny issue and not many (if any?) countries actually have a digital nomad specific visa. Visa rules and regulations are wide and varying by nationality, so you’ll need to research the exact requirements of your destination.

If you get a visa on your arrival, that’s taken care of. If not, you need to find out how to apply for your visa. It may be directly at your local embassy or it might be through a visa agency. While you’re at it, find out all the documents you will need for your visa and start to get them in order. This could include things like bank statements, proof of accommodation, or flight tickets.

Once everything is ready, apply for a visa well in advance. Don’t leave it till the last minute and wind up without documents or your passport. It could mess up your whole trip! Give yourself (and the embassy) enough time for the visa to be processed.

Another thing to keep in mind is that sometimes if you apply for a visa, you might be able to stay in a country longer than just a visa-exempt stamp on arrival. For example, many nationalities are exempt from a visa for Thailand so they can just show up and get a stamp in their passports that allows them to stay in the country for 30 days. However, if you apply for a visa in advance, Thailand gives you 60 days. So if you want to stay in a country longer, look into whether applying for a visa in advance is a better option.

The Actual Travel—Flights, Taxis, and More

Every seasoned traveller has their own hacks and secrets for booking flights and finding good deals. Typically, booking flights in advance often works out to be cheaper—and while sometimes you get an amazing last minute deal, I wouldn’t recommend leaving your bookings until the last minute. So instead of leaving things to the last minute…start researching ASAP. I start with Skyscanner.com and Kiwi.com—Kiwi.com is especially helpful because it combines flights from different airlines to get you the best deal. Google’s flight finder is another great one too.

This should also give you an idea of which airlines fly to your destination. Make sure you sign up to their newsletters—that way you’ll know when there’s a sale.

Beyond researching cheap airfare, you’ll need to get prepped on your actual travel logistics when you’re purchasing tickets. First: Figure out how much luggage you need, because if you’re not doing carry-on, some budget airlines will charge you for checked luggage. Don’t get caught paying a surprise bill!

Next, remember to check the arrival time. It’s always much less overwhelming if you arrive in a new place during the day, when there are more people around, the airport is lively, and transport is easier to find. Take it from me: I’ve made this rookie error and spent the whole time feeling completely on edge. To avoid this, research your airport—does it close at night? Are taxis easy to find? Do taxis work on a meter system or do you have to haggle? What are the other transport options to your hotel?

When you’re scheduling your trip, keep in mind that your flight will likely be downtime—meaning you might not be able to work. Internet isn’t a guarantee, so while you might get the chance to call into meetings and answer emails, you easily could lose the whole time you’re in the air. If you don’t have vacation days you can use for travel, you might want to schedule your trips for the weekend so you don’t lose a day.
Before you head to the airport, make sure you know how to get from your destination’s airport to your hotel. I always download the map for the city onto my phone on Google Maps, so I can follow the GPS even if I’m offline. The other option is to take screenshots of the location on the map and save them onto your phone in case you need to show your driver. Rome2Rio is a fantastic tool to start your research on how to get from Point A to Point B. It usually tells you train and bus options as well.

Finally, remember to give yourself enough time to recover post flight. Flying can be exhausting, especially over long distances, so don’t plan to jump into work immediately if you’ve just done a 15-hour flight. Give yourself time to relax and catch up on sleep.

Accommodations

We travel pretty slow and like to stay in one place for a few months. So, we usually don’t pre-book our apartments in advance. Instead, we book a hotel or an AirBnB for a few nights and then kick off our apartment hunt when we get there. We like to suss out the neighborhood and see the apartment in person before we commit for a longer stay.

You can book your initial accommodation via Booking.com, Agoda.com, AirBnB or if you’d like a hostel, try Hostelworld.com—I’ve had great experiences with all of these.

If you’re planning on finding an apartment when you get to your destination, be organized about it so you don’t waste time when you arrive. Start doing your research and getting prepared so you hit the ground running when you arrive. You’ll want to look into neighborhoods for both convenience and safety—I recommend nomad forums and personal blogs for the best information. If you find any apartments you like, set up some times to meet with agents or apartment owners when you arrive.

And when you’re back home booking accommodations, remember to save everything on your phone (or write it down). I suggest screenshotting your hotel name and address, and saving the booking details on your phone, too.

Travel Insurance

So here’s the thing. I never used to be a big believer in travel insurance. I have always had it because my partner always insisted on it. I went along but in my heart of hearts, I thought it was a waste of money.

But, in 2015, when we were living in Mexico I had an accident which required surgery. We also had to make an emergency trip back home. Our insurance came through and out of about $5000 worth of expenses, we maybe only paid about $100 out of pocket. I’m definitely a believer in travel insurance now!

So, get travel insurance!

Insurance companies and policies vary by region and country, so do your research and find out what is available to you. Be sure to read the fine print and confirm what you are covered for. You don’t want to be left in the lurch when you really need it. We use World Nomads, since they have health insurance, accident insurance, trip cancellation coverage, and coverage for our computers and other electronics.

Vaccinations and Other Medical Concerns

It’s always a good idea to have certain vaccinations when you’re traveling overseas. Some are precautionary, while others might be part of the entry requirements of a country. For example, many South American and African countries will ask for proof of yellow fever vaccination. Thankfully this vaccine is valid for 10 years, sometimes even your whole life so you don’t have to worry about it too often.

What vaccines you need specifically will vary by where you plan on going but some ones to consider include rabies, typhoid, Hepatitis A and B, and tetanus. The best thing to do is to go to a travel doctor—they usually know what you need and what you don’t. You should also look up your government’s health advisory websites.

If you have any other medical concerns or need to take certain medication regularly, it’s definitely a good idea to start looking into things as soon as you can. Speak to your doctor and your health insurance company, as they may have restrictions on bulk filling your prescriptions before you go and you’ll need your doctor to sign off. This can be a real headache, so I cannot overstress enough the need to start planning and organizing this well in advance.

Packing

Unlike many digital nomads, we are not carry-on only travelers. There is no right or wrong way, so just do what suits you.

The first time you embark on a trip, you will probably bring much more than you need. You’ll see what works and what doesn’t and refine from there. The internet is full of packing lists (see: this minimalist-packing list, for example), but here’s what to pay extra attention to:

  • Tech gear: Make sure you have everything you need to get work done such as your computer, travel adapters, hard drive etc.
  • Appropriate clothing: Bring clothes that are not only appropriate for weather but also culturally appropriate. Do your research to learn more about this.
  • Shoes: Bring comfortable shoes. That is all.
  • Toiletries: Thankfully, you can get most things overseas so don’t bring a whole lot more than what you need for the first few days. The rest you can just buy when you get there.

A version of this post previous appeared on Fulltime Nomad.

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2 comments

  1. Anonymous Replied

    The best thing to do is to go to a travel doctor—they usually know what you need and what you don’t. 

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