Step-by-Step: How I, as a Digital Nomad, Plan Trips to New Places

As a digital nomad, the thrill of setting foot in a new country, city, or locale never gets old. Exploring new sights, immersing myself in diverse cultures, and meeting new people is a huge part of what makes the digital nomad lifestyle so captivating. But getting from point A to B is not always as simple as it seems. That is where my personal travel planning strategy comes in.

This strategy is not something that was built overnight. Over the past decade of my digital nomad journey, I have refined and honed my approach, learning from each trip to make the next one smoother. I am going to share with you my step-by-step guide on planning travels, but bear in mind this is highly personalized. It is what works for me, but it might not be the perfect fit for everyone.

To better illustrate these steps, I will use my last journey as an example - how I planned my trip from The Hague, the Netherlands, to Sofia, Bulgaria.

Step 1. Research Phase

My journey to a new place starts long before the physical journey - with comprehensive research. I make use of YouTube and articles to gather information about my destination and create a list of must-visit places.


With my destination decided, my first move is to turn to YouTube. I find it to be an excellent source for getting a taste of what awaits me in my next stop. In this case, I hit the search bar and enter "Sofia Bulgaria what to see" and "Sofia Bulgaria best things to do". There is something about seeing the city come alive in video form that fuels my anticipation and gives me a clearer sense of what to expect. It is like getting a sneak peek of my upcoming adventure.

Step-by-Step: How I, as a Digital Nomad, Plan Trips to New Places. Research Phase

Step 2. Mapping

Next, I take my research from Step 1 and place it into a more tangible form - on Google Maps. Creating a dedicated list for the trip helps me visualize my plans and organize my thoughts. If I am not planning to get a SIM card for the destination, I rely on as it allows offline access to detailed maps.


In this first step, my search led me to a captivating video titled, "Watch before you go! 🇧🇬 There is so much to see in SOFIA BULGARIA България." As I watched, I diligently pinned each highlighted location onto my Google Maps list called "Sofia, what to see". This living document will serve as my personal travel guide, continually expanding as I discover more unique places during my trip. See the image below for a snapshot of my ongoing map.

Step-by-Step: How I, as a Digital Nomad, Plan Trips to New Places. Mapping PhaseBy the way, if you are interested in seeing my personalized list and perhaps drawing some inspiration for your own travels, feel free to direct message me on Twitter. I am always delighted to share my nomadic findings with fellow travelers!

Step 3. Transportation

Finding the best way to reach my destination is often an adventure in itself. Depending on the location, the options range from planes and buses to ferries and cars.For flights, I usually kick-start my search with aggregators such as Aviasales and Skyscanner, then proceed to the websites of budget airlines, which often provide deals not shared with the aggregators. For European destinations, my go-to airlines are Ryanair, EasyJet, and Wizzair, while for Asia, I often check AirAsia.

A crucial tip here is to utilize a VPN and open incognito tabs when browsing for flights. This is because airlines frequently display different prices for various regions. For overland travel or more alternatives, I check out platforms like Rome2Rio and

When it comes to exploring Europe, bus travel is an excellent, cost-effective option. Services like Flixbus and Ecolines offer extensive networks across the continent, providing another feasible choice for moving from city to city.

Lastly, always considering nearby cities as potential starting points can lead to significant savings. For instance, even though Siem Reap in Cambodia has its own airport,it can be cheaper to fly to Bangkok and then take a bus from there. Flexibility with travel dates can also yield better deals, so It is worth having an open schedule whenever possible.


As I embarked on my journey from The Hague to Sofia, I quickly realized that my best option would be to fly due to the substantial distance between the two cities. I diligently scoured through flights from all Dutch airports, focusing primarily on Amsterdam and Eindhoven, and all flights heading to Sofia.
To broaden my search and possibly discover a cheaper or more convenient option, I also checked for combinations of flights and bus rides that might work in my favor. This involved looking into flights going to Belgrade and then catching a Flixbus from there to Sofia.
After thorough research using Skyscanner, the winner emerged - a flight from Eindhoven to Sofia on the budget airline Wizzair.

Step-by-Step: How I, as a Digital Nomad, Plan Trips to New Places. Transportation Phase

Step 4. Accommodation

Once I have locked down my travel dates, It is time to find a place to stay. To understand the best areas to stay, I either refer back to my Google Maps list or check out Hoodmaps, a tool that gives insights into the best and upcoming areas in a city.

Then, I open up Airbnb,, or and start my search. Remembering to use a VPN here too is crucial, as prices can vary based on location, and often offers better prices on its mobile app than on its website. It is also worth noting that checking the websites of the hotels you find might result in better deals, as direct purchases can be cheaper.

For budget management, I recommend opting for a place with a kitchen and washing machine, which helps reduce costs on meals and laundry.


Once I knew my arrival date in Sofia, I explored Hoodmaps to grasp the best neighborhoods (check the image below). Then, I compared prices on Booking, Trip, and Airbnb. In the end, an Airbnb with a kitchen and washer offered the best value for my stay.

Step-by-Step: How I, as a Digital Nomad, Plan Trips to New Places. Accommodation Phase

Conclusion 1. Embrace Flexibility

One of the most important parts of being a digital nomad is the ability to stay open to changes. The booked apartment may not meet your expectations, or the area may not be what you anticipated. Being able to adapt and modify plans is key to maintaining a stress-free nomadic lifestyle.

Conclusion 2. Further Reading

For more insights into my digital nomad lifestyle, consider checking out my book, "Digital Nomad Life: Ultimate Guide". It offers a comprehensive look at my experiences and lessons learned from leading a life of travel and remote work.

Stay up to date

Get notified when I publish something new, and unsubscribe at any time.