After more than a decade of living and working on the road, we’ve learned a lot about what makes or breaks a destination – not just as a place to stay. visitbut as a place to actually live and work. Believe me, these are two very different things!
Since 2012, we have been present in dozens of countries around the world.
Some places (like Thailand, MaltaBarbados, Guatemala, Baliand Montana USA), we spent about 2 months there. While others like Lisbon, Playa del CarmenChina & Grenadewe ended up spending between 6 months there… or more than a year!
Today we consider Bulgaria our home base, but we leave around half the year to discover other parts of the world.
Over time, we developed a checklist – a set of filters that we use for each new destination before committing to spending more than a month there.
If you’re trying to figure out where to install your laptop next, this is exactly what we’re looking for in a digital nomad destinationand what you might also want to consider.
1. Nature (Our Non-Negotiable)
This one is at the top of our list for a reason. No matter how good the wifi is or how affordable the cost of living is, if we’re surrounded by concrete with no access to the outdoors, it’s not going to work for us. Nature is always the first filter we apply.
Of course, what this looks like varies depending on the destination. In Thailand it was jungle and beaches, and in Montana it was mountains and wide open skies. In Barbados, Mexico and Grenada it was the sea, literally just a few steps away.
Even during our stay in Lisbon, the Tagus River flowed alongside the city and the beaches were also nearby.
Bulgaria ticks this box better than almost anywhere we’ve lived: it has mountains, rivers, hiking trails, and the Black Sea coast, all within a few hours. This is a large part of the reason we chose it as our home base.
Ask yourself: what kind of nature recharges you (if any)? Then make sure your base has it nearby. Without it, even the most “perfect” destination will start to feel like a cage.
2. Cost of living/quality of life ratio
This is where people go wrong most often. Either they are looking for the the cheapest possible destinations, or assuming that spending more money automatically means living better – which is not always the case.
The true sweet spot is where your money goes far enough that you’re not stressed, but you’re also not sacrificing quality of life to save a few dollars.
For us, that means great dining options (local AND international), comfortable accommodations, and the ability to easily indulge in experiences like day trips, restaurants, and activities.
We found incredible value in countries like Southeast Asia (Vietnam, Indonesia, and Thailand), Latin America (Argentina, Guatemala, Playa del Carmen), and Europe (Bulgaria, Cyprus, Montenegro, Croatia, Albania, Georgia).
We always think: can we live comfortably, cover all our business expenses, save money AND enjoy here? If yes, we are in the right place.
Another great way to save on hosting costs is to become a house and pet sitter (in exchange for taking care of someone’s house and pet, you get free accommodation).
This is something we have been doing for many years and have had best life experiences in Costa Rica, Grenada and Barbados. We found our job thanks Trusted house sitters and they currently run a 30% off promo registration fees. Click here for more details.
3. Amenities
This one seems boring until you’re in a 2 week base and realize you can’t find a decent coffee shop, gym, or grocery store that carries anything other than the basics. Just like when you live at home, amenities matter.
By this I mean the practical infrastructure of daily life. Being able to find reliable supermarkets, good restaurants and cafes (especially those with wifi for working), coworking spaces, gyms or yoga rooms, pharmacies, banks, reliable transportation, etc.
The longer you plan to stay somewhere for several months, the more these daily details affect your quality of life.
Grenada and Barbados were incredible for their nature and relaxed lifestyle, but amenities were limited compared to a city like Lisbon, Buenos Aires, or the digital nomad hub of Bali. This is therefore something to take into account if you have specific needs.
This one took us years to fully appreciate. When we started, we thought community was “nice to have.” We now believe that this could be one of the most important factors, especially for mental health and long-term motivation.
When you’re surrounded by people who are also starting businesses, working remotely, and living regardless of where they live, it’s empowering.
You exchange advice, create collaborations and make real friends. When you’re isolated, even the most beautiful place starts to feel lonely…
Look for cities with active nomadic Facebook groups, regular meetups, and coworking spaces that double as social hubs. Playa del Carmen, Uluwatu, Ubud, Canggu and Chiang Mai are classic examples of places with a strong and integrated nomadic community.
5. Fun things to do
Of course, it’s not just about working on your laptop! You must also actually live wherever you are. A destination that has nothing to do outside of working hours gets old quickly, no matter how cheap or well-connected it is.
Things to do are different for everyone. For us, it’s hiking, fly fishing, exploring local culture, going to wine and beer bars, trying new foods, or taking weekend road trips. For you, it might be nightlife, live music, museums or a surfing trip.
This is also where having a “base” really pays off. When you stay somewhere for a month or more rather than passing through as a tourist, you can dive deeper into the destination and live a little more like a local rather than a tourist.
We had house and pet care jobs in Costa Rica, Grenada and Barbados, and it was a great way to really get to know the places we were visiting.
6. Connectivity (WiFi and Data)
As a digital nomad, you will know the importance of a strong internet connection. No matter how many amenities or amazing restaurants there are somewhere, when you have to work and the internet isn’t stable, all the conveniences in the world won’t matter.
Before we commit to staying somewhere, we research average Wi-Fi speeds, look for recent reports from nomads in Facebook groups and Reddit threads, and if possible, we’ll even ask the host/owner to send us a screenshot of internet speeds – download and upload.
Choosing a destination with a coworking scene is also a good option – even if the apartment’s wifi is slow, a good coworking space is the backup plan. We were never great coworkers, but in Bansko we tried for about a month and really enjoyed the community vibe.
On the data side, one thing we’ve relied on over the years is traveling with a global eSIM. We’ve used them in several countries and we certainly don’t miss the days of physical SIM cards – having to find them has always been a nightmare.
With a global eSIM, you charge it before you leave and you’re online when you land. Whether you’re doing a trial run at a potential new base or taking weekend trips from your new base, sorting out the data before you arrive removes one extra point to worry about.
Plus, you can use your phone as a hotspot and connect your laptop! Discover the Mozilla Travel eSIM – it covers 201 countries with their Global diet on a single reusable eSIM, which is exactly what this type of lifestyle demands.
7. Location (airport access and proximity)
It’s a practical question that’s easy to forget when dreaming of a destination…until you’re forced to take a 36-hour journey every time you want to travel, visit family, or move on to your next base.
Here’s what we always consider: How far is the nearest international airport? How well connected is it? How long and how much does the trip cost if we have to return home to Canada at the last minute?
Bulgaria is doing quite well in this category. We wish the airport was closer (it’s a little over 2 hours drive to Sofia airport). But it offers direct flights across Europe and beyond, and we can reach most major European cities in less than three hours.
When we were based in Playa del Carmen, the Cancun airport was only a 45-minute drive away and had direct flights to most of North America. Being a Caribbean island, Grenada was the trickiest – beautiful, but going anywhere else involved connections and expense.
You need to think about your goals/projects. If you are a frequent traveler in your nomadic life, this factor alone can save you a huge amount of time and money over the course of a year.
8. Health care
It’s not the most exciting thing to look for, but one of the most important, especially if you plan to stay somewhere for months. I’ll be honest, it’s only recently that we’ve started to really think about healthcare on the road (we’re getting older, after all!).
Nowadays we always ask ourselves: is there a decent hospital or clinic nearby? Is private healthcare affordable? Are we covered by travel insurance that works here? What is the standard of care for more serious problems?
In most countries in Southeast Asia and Europe, private healthcare is excellent and affordable. In some smaller island destinations in the Caribbean and parts of Latin America, infrastructure is more limited – which doesn’t mean you shouldn’t go, but it does mean having solid travel insurance is essential.
From our personal experience, Bulgaria is definitely a mixed country when it comes to healthcare. There are definitely pros and cons.
The advantage is that you can consult a specialist within the day and it is very affordable. The disadvantages being the quality of the installations in some cases and the year-round bedside. But we have international travel insurance for any serious problems. For digital nomads and remote workers, Security wing has insurance plans that suit this lifestyle well.
9. Security
Security is contextual and definitely personal. What seems comfortable to one person may be stressful to another (especially men versus women), and crime statistics don’t always match actual experience on the ground.
My advice is to read recent accounts from nomads who have actually been there, not just government travel advisories.
You’ll usually find a real picture of day-to-day safety in Facebook groups, Reddit threads, YouTube videos, and blog posts written by people currently based there.
Beyond security in terms of crime, also think about everyday comfort.
Is it easy/safe to get around? Can you walk to a restaurant in the evening without stress? Are there any neighborhoods that are clearly better to stay in than others? What if we got scammed?
And also think about environmental safety. Maybe try to avoid known hurricane seasons in some destinations (we experienced 2 hurricanes…), or visit in peak season with extreme heat, and also consider mountain and ocean safety.
Do your research, be smart, and don’t let fear-based headlines stop you from exploring.
10. Visa situation
Unless you plan to travel every month or so, nothing is more annoying than realizing you have to make a border crossing every 30 days. Before settling somewhere, we always think about the visa situation.
The good news is that there are more options than ever right now!
Countries like Spain, Portugal, Colombia, Cyprus, Croatia, BaliAnd Georgia all have clear pathways for digital nomads – official nomad visas, long-stay tourist visas or remote work permits.
Georgia is still one of the most flexible countries in the world, with visa-free stays of up to a year for most nationalities. And for Americans, Albania also offers a one-year stay.
Thailand now has the Destination Thailand Visa (DTV), a 5-year multiple-entry visa that allows you to stay up to 180 days per entry (expandable to 360), which is one of the most flexible long-stay options we’ve seen.
Mexico does not have an official visa for digital nomads, but the Temporary resident visa works just as well in practice: it’s granted for one year and renewable for up to four, and thousands of remote workers use it as a legal route to live and work there long-term.
Do your homework before you land. Know how long you can legally stay, what extension options there are, and if there are any restrictions on earning income remotely.
Additionally, everyone’s tax situation is different, so it’s important to speak to an accountant to ensure you don’t trigger tax residency.
It’s not as complicated as it seems once you’ve done it a few times, but it’s always worth sorting it out before booking the flight.
Trust your instincts after the first week
All the research carried out in the world does not replace presence in the field. After a week in any destination, all you need is know if it has the right energy for you.
Maybe something looks good on paper, but you just don’t accept it. Don’t ignore your instincts. If you plan to stay for a few months, try giving it a trial run before committing to a longer stay.
Take a week or two before signing a three-month lease and give yourself permission to change it if you just aren’t feeling it! That’s kind of the whole point of this lifestyle, right?