Dose #2 Jet-Set Go: How to Pick Your Digital Nomad Travel Destination?

6 things to consider when deciding your travel destination with insights from my travel experience!

Hello there!

How are you doing this week? I, for one, can tell you that the past week has been very sunny. I had a migraine for 2 days straight and spent most of the day walking around indoors in sunglasses. People must have thought that I had a hangover.

Did I tell you it’s sunny here?

Now that we've got the weather updates out of the way, let’s delve into why we are here.

In the last edition of the newsletter, we explored answers to the questions:

  • Who is a Digital Nomad?

  • What are the pros and cons of being a digital nomad?

  • Where to start if you want to become a nomad? Read them here

As Mark Mason says, "The solution to one problem is merely the creation of the next one." So let’s start solving our next problem.

How to Pick Your Digital Nomad Travel Destination?

Deciding on the city to plant your roaming roots is more than just throwing a dart on a map. It's about aligning the place with your pace.

Let’s go into how you can pick a destination that not only meets your wanderlust cravings but also fits well with your lifestyle.


Before diving into the endless pool of possible destinations, take a moment to reflect. What fuels your spirit—mountains, beaches, bustling cities, or quiet towns? What kind of cultures intrigue you?

Jot down your preferences; it’s the first step in aligning your travel goals with your heart’s desires.

I love bustling cities but cities like Chiang Mai (Thailand) and Pokhara (Nepal) were more memorable. So it’s safe to say that I prefer nature.


Now, let’s do some digging. Explore various destinations online, read blogs, and engage in travel communities. Note down your preferences for the shortlisted spots under each of the following topic when you are researching;

Best Time to Travel & Climate

Timing is everything, isn’t it? The climate and the season can be game-changers. Here’s a little rundown on how to factor in the skies and the calendars:

  1. Seasons: Each place has its rhythm with the seasons. Some destinations are magical in winter, while others bloom in spring. Research the best seasons to visit your shortlisted spots.

  2. Festivals and Events: Local festivities can be a treasure trove of cultural and community experiences. Check the local calendars for events or festivals that pique your interest. It could add a whole new dimension to your stay!
    From my experience, both Malaysia and Singapore are excellent destinations to witness Chinese New Year (CNY) celebrations, and Kathmandu, Nepal to witness Deepavali (Diwali)! Since I work with startups, I do my research around tech and community conferences as well.

  3. Weather Patterns: If you're someone who thrives in the sunshine, a place with a mild, sunny climate might be up your alley. Look into the typical weather patterns to ensure you pack right and set up shop comfortably.
    I try to avoid Monsoon seasons in Thailand and Sri Lanka at all costs. The weather in San Francisco is nice from September - November it seems. I can tell you for sure that it’s at its best in October. With Climate Change weather patterns have changed a bit, so better to cross-check with locals to confirm the weather in a city.

  4. Off-Peak Travel: Travelling during the off-peak season could be a smart move. It often means fewer tourists, lower prices, and a more relaxed pace. Plus, it's easier to find a quiet corner in a cafe to work on your laptop.
    I travelled to the Southern part of Sri Lanka (Hiriketiya and Ahangama) during off-peak and had the best time exploring beaches and nature quietly.

  5. Climate-Driven Activities: Are you a surf enthusiast or a snow sports lover? Your hobbies could very well dictate your next stop. Pick a place where the climate aligns with your outdoor interests.
    Sri Lanka is a great surf spot with two surf seasons and plenty of yoga retreats and tropical fun-time activities!

Did you spot the cute dog with a marigold garland? This is a Deepavali (Diwali) festival tradition I witnessed while I was in Nepal.

Budget Considerations

Find out the cost of living of the city you want to travel to. You can do a simple Google search and find that out using multiple blogs and websites that do such calculations. When reading up, make a note of these costs - accommodation, flights and other transportation costs, telecommunication expenses (purchasing a SIM and Wi-Fi), food, coffee, and recreation costs.

It would be overwhelming at first but don’t forget that there are amazing budget-friendly destinations that don’t skimp on the adventure! This is an extensive topic that we can dig deep into later.

Health and Safety

Your health and safety should never take a backseat. Look into travel advisories, local health precautions, and necessary vaccinations. It’s better to purchase travel insurance when entering some countries, so make a point to research if such requirements exist and what other travellers/digital nomads do.

Visa and Entry Requirements

Don’t let visa woes clip your wings. Check the visa requirements and other entry protocols of your chosen destinations. Some places offer digital nomad visas, which could be your golden ticket.

As a Sri Lankan Passport holder, I have had my fair share of visa-processing drama 😄 

So here are 2 tips for those who travel with a relatively weak passport:

  1. If you are a first-time traveller or if you have travelled only to a very few destinations, don’t choose countries like the UK, Schengen, and US on the get-go. They are said to have strict visa entry requirements. Choose tourist-friendly countries as your first few stops. For example, Thailand, Vietnam, and Malaysia are great destinations!*

  2. Choose countries with visa-on arrival: Every passport is qualified for a set of countries for visa-on arrival. Find which countries your passport qualifies for a visa-on arrival and add 1 or 2 of them to your list. Please note that the visa-on arrival is valid for a certain period and it differs from country to country. So check all the applicable conditions before making a decision.*

Digital Nomad-Friendly Amenities

A reliable internet connection is your lifeline, and a cosy co-working space is a must. Ensure your chosen locale caters to your digital needs. It’s all about blending work with your explorations seamlessly.

I still remember having a hard time with connectivity while exploring certain parts of Penang in Malaysia! It was entirely my fault since I didn’t plan the exploring and working properly on that day, but you’ll face frustrating moments like this, now and then.


Being around like-minded can be the cherry on top of your nomadic adventures. Look for places with thriving digital nomad communities. It’s not only about the shared Wi-Fi but the shared experiences and inspirations.

I am connected to a vibrant community called Asian Wonder Women, and I get in touch with fellow community members before travelling to a country, so that we can meet up!

Always get to explore different sides to the cities I visit with the friends I have made on this journey!

Your perfect destination is not just a point on the map, but a match to the lifestyle you want. So use the above guidance and find what works best for you!

These are honestly simple things I consider when planning a trip.

I do my planning and prepping on Notion. I’ll share more details in the next edition on how I prep for a trip using a Notion template along with a few recommended apps to use.

This is it for this week, let me know what you think by hitting a reply to this email or connecting with me on LinkedIn.

Disclaimer: The insights shared in this newsletter are based on my personal experiences and research. They are not meant as legal or official travel advice. For such guidance, please consult relevant authorities or professionals. Happy exploring!

I want to help you to travel better, be productive and remote work effortlessly.

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