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 visit, but as a place to actually live and work. Trust me, those are two very different things!
Since 2012, we’ve based ourselves in dozens of countries around the globe.
Some spots (like Thailand, Malta, Barbados, Guatemala, Bali, and Montana USA), we spent around 2 months there. While others like Lisbon, Playa del Carmen, China & Grenada, we ended up spending between 6 months…or more than a year!
These days, we call Bulgaria our home base, but we leave for around half the year to experience other parts of the world.
Over time, we’ve developed a checklist – a set of filters we run every new destination through before we commit to spending more than a month there.
If you’re trying to figure out where to plant your laptop next, here’s exactly what we look for in a digital nomad destination, and what you might want to consider as well.
1. Nature (Our Non-Negotiable)
This one tops 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 won’t work for us. Nature is always the first filter we apply.
Of course, what that looks like varies by destination. In Thailand it was jungle and beaches, and in Montana it was mountains and wide open sky. In Barbados, Mexico and Grenada it was the sea – literally steps away.
Even during our city stay in Lisbon, there was the Tagus River running along the city, and the beaches were nearby as well.
Bulgaria actually 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. It’s a big part of why 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 vs. Quality of Life Ratio
This is the one people get wrong most often. They either look for the cheapest destinations possible, or assume spending more money automatically means living better – which isn’t always the case.
The real sweet spot is where your money stretches far enough that you’re not stressed, but you’re not sacrificing quality of life to save a few dollars either.
For us, this means good food options (local AND international), comfortable accommodation, and the ability to easily afford experiences like day trips, restaurants, and activities.
We’ve found incredible value in places like Southeast Asia (Vietnam, Indonesia & 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 ourselves here? If yes, we’re in the right place.
Another great way to save on accommodation costs is to become a house and pet sitter (in exchange for taking care of someone’s home and pet, you receive free accommodation).
This is something we did for many years and had the best experiences living in Costa Rica, Grenada and Barbados. We found our jobs through Trusted Housesitters and they’re currently running a promo of 30% off the signup fee. Click here for details.
3. Amenities
This one sounds boring until you’re 2 weeks into a base and realize you can’t find decent coffee, a gym, or a grocery store that stocks anything beyond the basics. Just like when you’re living at home, amenities matter.
By this, I mean the practical infrastructure of daily life. Being able to find reliable supermarkets, good restaurants and cafés (especially ones with wifi you can work from), coworking spaces, gyms or yoga studios, pharmacies, banks, reliable transport, etc.
The more months you plan to stay somewhere, the more these everyday details affect your quality of life.
Grenada and Barbados were incredible for nature and relaxed lifestyle, but the amenities were limited compared to a city like Lisbon, Buenos Aires, or the digital nomad hub of Bali. So, this is something worth factoring in if you have specific needs.
This one took us years to fully appreciate. In our early days, we thought community was a “nice to have.” Now we think it might be one of the most important factors – especially for long-term mental health and motivation.
When you’re surrounded by people who are also building businesses, working remotely, and living location-independently, it’s energizing.
You swap tips, create collaborations, and make real friends. When you’re isolated, even the most beautiful place starts to feel lonely…
Look for cities with active nomad 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, built-in nomad community.
5. Fun Things to Do
Of course, it’s not all about working on your laptop! You also need to actually live wherever you are. A destination with nothing to do outside of work hours gets old quickly, no matter how cheap or well-connected it is.
Things to do looks different for everyone. For us it’s hiking, fly-fishing, exploring local culture, wine and beer bars, trying new food, or weekend road trips. For you it might be nightlife, live music, museums, or a surf break.
This is also where having a “base” really pays off. When you’re staying somewhere for a month or more rather than passing through as a tourist, you get to dive deeper into the destination and live a little more like a local rather than a tourist.
We had house and pet-sitting jobs in Costa Rica, Grenada and Barbados, and it was such a great way to properly experience the places we were visiting.
6. Connectivity (WiFi & Data)
As a digital nomad, you’ll know the importance of a strong internet connection. It doesn’t matter how many amenities or amazing restaurants somewhere has, when you have to work and the internet isn’t stable, all the amenities in the world won’t matter.
Before committing to staying somwehwere, we research the average wifi 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 the internet speeds – upload and download.
Choosing a destination with a coworking scene is also a good option – even if the apartment wifi is slow, a good coworking space is the backup plan. We’ve never been huge coworkers, but in Bansko we gave it a try for a month or so and really enjoyed the community vibe.
On the data side, one thing we’ve come to rely on over the years is travelling with a global eSIM. We’ve used them across multiple countries and we definitely don’t miss the days of physical SIM cards – having to find them was always a nightmare.
With a global eSIMYou load it before you leave, and you’re online when you land. Whether you’re doing a trial run at a potential new base, or making weekend trips from your new base, having data sorted before you arrive removes one more thing to stress about.
Plus, you can use your phone as a hotspot and tether your laptop! Check out the Mozillion Travel eSIM – it covers 201 countries with their Global Plan on a single reusable eSIM, which is exactly what this kind of lifestyle calls for.
7. Location (Airport Access & Proximity)
This is a practical one that’s easy to overlook when you’re dreaming about a destination…until you’re stuck doing 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 close is the nearest international airport? How well connected is it? How long and expensive is the journey if we need to be home in Canada at the last minute?
Bulgaria does pretty well in this category. We wish the airport was closer (it’s a little over 2 hours to drive to the Sofia airport). But, it has direct flights across Europe and beyond, and we can be in most major European cities in under three hours.
When we were based in Playa del Carmen, the Cancún airport was just a 45-minute drive and served by direct flights to most of North America. Being an island in the Caribbean, Grenada was the trickiest – beautiful, but getting anywhere else involved connections and expense.
You have to consider what your goals/plans are. If you’re a frequent traveller within your nomad life, this factor alone can save you enormous amounts of time and money over the course of a year.
8. Healthcare
Not the most exciting thing to research, but one of the most important – especially if you’re planning to stay somewhere for months at a time. I’ll be honest, we’ve only recently started really considering healthcare on the road (we’re getting older, after all!).
These days, we always look at: Is there a decent hospital or clinic nearby? Is private healthcare affordable? Are we covered by travel insurance that works here? What’s the standard of care like for more serious issues?
In most of Southeast Asia and Europe, private healthcare is excellent and affordable. In some smaller island destinations in the Caribbean, and places in Latin America, the infrastructure is more limited – which doesn’t mean you shouldn’t go, but it does mean having solid travel insurance is essential.
In our personal experience, Bulgaria is definitely a mixed bag when it comes to healthcare. There are pros and cons for sure.
Pros being that you can see a specialist within a day, and that it’s very affordable. Cons being the quality of facilities in some cases and the bedside manner. But, we have international travel insurance for any serious issues. For digital nomads and remote workers, SafetyWing has insurance plans that work well for this lifestyle.
9. Safety
Safety is contextual and definitely personal. What feels comfortable to one person might feel stressful to another (especially men vs. women), and crime statistics don’t always match the lived experience on the ground.
My advice is to read recent first-person accounts from nomads who’ve actually been there, not just government travel advisories.
You’ll usually find the real picture of day-to-day safety in Facebook groups, Reddit threads, YouTube videos and blog posts from people currently based there.
Beyond safety in terms of crime, think about daily comfort as well.
Is it easy/safe to get around? Can you walk to a restaurant at night without stress? Are there neighbourhoods that are clearly better to stay in than others? What about getting ripped off?
And also, consider environmental safety. Maybe try to avoid known hurricane seasons in certain destinations (we’ve experienced 2 hurricanes…), or visiting in the high season with extreme heat, and consider mountain and ocean safety as well.
Do your research, be street-smart, and don’t let fear-based headlines stop you from exploring.
10. Visa Situation
Unless you plan on moving around every month or so, nothing is more annoying than realizing you have to do a border run every 30 days. Before basing ourselves anywhere, we always figure out the visa situation.
The good news is there are more options than ever right now!
Countries like Spain, Portugal, Colombia, Cyprus, Croatia, Bali, and Georgia all have clear pathways for digital nomads – official nomad visas, long-stay tourist visas, or remote worker 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 offers a year-long stay as well.
Thailand now has the Destination Thailand Visa (DTV), a 5-year multiple-entry visa that lets you stay up to 180 days per entry (extendable to 360), which is one of the most flexible long-stay options we’ve seen anywhere.
Mexico doesn’t have an official digital nomad visa, 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 their legal pathway to live and work there long-term.
Do your homework before you land. Know how long you can legally stay, what the extension options are, and whether there are any restrictions on earning income remotely.
Plus, everyone’s tax situation is different, so it’s important to speak with an accountant to make sure you don’t trigger tax residency.
It’s not as complicated as it sounds once you’ve done it a couple of times, but it’s always worth sorting out before you book the flight.
Trust Your Gut After Week One
All the research in the world doesn’t replace actually being on the ground. After a week in any destination, you just know whether it has the right energy for you.
Maybe somewhere sounds good on paper, but you just don’t jive with it. Don’t ignore your instincts. If you’re planning to stay for a couple of months, try to do a trial run before committing to a longer stay.
Do a week or two before you sign a three-month lease, and give yourself permission to change it up if you’re just not feeling it! That’s kind of the whole point of this lifestyle, isn’t it?
