5 Top Spots to Start Your Digital Nomad Journey

Not all who wander are lost,” said J.R.R. Tolkien. In fact, for many, being a wanderer is the lifestyle of choice, especially if the alternative means sitting in commuter traffic and being chained to the same desk, day in and day out.

In our increasingly digital world, the idea of “the office,” with its rows of monochrome desks, florescent lighting, temperamental printers, and bland coffee, is quickly losing its status as the working-world’s modus operandi. Today’s office, whether there’s a physical location or not, exists primarily on the cloud and is accessible from anywhere that has WiFi.

The cloud office isn’t constrained by location or by traditional working hours, and it has equipped us with myriad fresh options when it comes to the workplace. The most exciting of which is the ability to take a more nomadic approach to earning an income.

Untethered workers, or digital nomads, are a growing group of people who have decided to rip up the old rules of the game and use these new advances in telecommunications to travel as much as possible and live in whatever part of the world they choose. Among their ranks you’ll find a whole spectrum of professions, including software developers, graphic designers, copywriters, and consultants—both working remotely for their employers and freelancing.

These benefits aren’t just the prerogative of millennials. Baby boomers are also taking to nomadic life in significant numbers, using it as a way to enjoy more travel, scout potential retirement destinations, take advantage of cheaper healthcare costs, and cut down on their workload.

Whether you’re thinking about remote working or creating a freelance income, or you already have one, there is a world of options available to you. To help you narrow in on a destination, and give you a taste of what the untethered life is all about, we’ve compiled our top five destination recommendations for boomer digital nomads.

Medellín, Colombia

Digital Nomad in Medellín, Colombia

After spending 10 years sitting in a cubical working as a data analyst for a U.S.-based company, Amanda Brightwater decided she had had enough. “I was feeling very confined working in an office,” she explains. “I could have stayed with my same company and worked remotely from home, but I wanted to see the world.”

With travel in mind, Amanda started her own online analytics business, sold her furniture, and packed a suitcase.

“When I started looking into places that were conducive to digital nomad lifestyle, Medellín kept popping up as an up-and-coming destination. I’ve met so many interesting people who are working here with just a laptop, a cellphone, and a comfortable place to hang out. I initially came for the comraderie, but discovered I love the weather, the culture, and the excitement of the city.”

Despite having nearly 3 million inhabitants, Medellín has a relaxed vibe, feeling more like an expanse of neighborhoods connected by parks and green spaces than a large metropolis. Yet there is no short supply of museums, art galleries, concert venues, restaurants, and places to whet your whistle. More than 30 universities add to the cultural life of the city, with regular free concerts, plays, and dance performances. For excursions away from your laptop, there are hiking trails through the nearby Antioquia Mountains, as well as horseback riding, and flying parepente (seated hang gliding).

Over the past few decades, Medellín has shaken off the shadow of its dark past to become one of the most progressive cities in the world, winning awards for innovation and design, and earning the moniker “Medellín Miracle” for its impressive social transformation. As such, it has attracted digital nomads in search of up-and-coming, low-cost destinations in droves, and now has a well-established remote working infrastructure.

Medellín has publicly available WiFi all over the city, but you won’t be short of cafés where you can find faster speeds. Airbnb rentals will typically offer speeds of between 10 and 20 mbps, but you can find between 100 and 300 mbps in many of the co-working spaces throughout the city.

During the past five years, the number of co-working spaces in Medellín has grown exponentially. You can find whatever type of space suits your working needs. They can be well-organized formal settings with a corporate, interactive vibe; quiet, small, intimate spaces; or hot desks (unassigned desk space in an open plan office). In Selina, a popular co-working space in the popular El Poblado area, a hot desk will only cost you $100 per month, or $8 for a day.

The exchange rate in Colombia has been hovering around 3,000 pesos to the U.S. dollar for about the past three years. This makes an already low cost of living even lower. It is possible to live on $1,500 to $2,000 per month in many parts of Medellín.

Lisbon, Portugal

Digital Nomad in Lisbon

“Lisbon is full of amazingly creative talent, cozy cafés, exciting co-working spaces with high-speed wireless internet, and a deep-rooted global view that’s hard to find anywhere else,” says Californian Kevin Mullins, who relocated to Portugal in 2010, fell in love with the country, and stayed. Today, he’s the managing director of Atomivox, a branding agency based in the seaside town of Cascais, just a few miles west of Lisbon.

“The wonderful coastal weather, amazing food and wine, and entrepreneurial spark among Portuguese friends and business associations made it so easy to settle here,” he says.

Lisbon was always a top candidate for the most popular city in Europe for digital nomads. It is one of the cheapest capital cities in Western Europe; it has 300 days of sunshine per year; the winters are mild; the nightlife, coffee, and food scene can compete with anywhere in the world; there is access to beaches; great healthcare; and the powerful allure of yellow trams, azulejos tiles, terracotta rooftops, and custard tarts make it irresistible.

But what makes Lisbon exceptional is how well it has adjusted to the influx of digital nomads. It has a reputation as one of the most welcoming digital nomad scenes in the world—designated both the fourth safest (Global Peace Index) and friendliest country in the world to expats (Far and Wide). There are digital nomad meetups held every week, with active Facebook groups and events run by digital nomad accommodation startups like NomadX. And, perhaps the biggest indicator of all that Lisbon aims to position itself as a digital nomad stronghold, the city has hosted the Web Summit, dubbed “the best technology conference on the planet” by Forbes Magazine, since 2016.

Lisbon has many co-working options available, and with a few exceptions, prices tend to hover around the same rate. You can easily find a hot desk to do your work for proximately $13 a day, or $112 to $250 for a month.

Each different co-working space offers something unique. In Lisbon’s Alcântara neighborhood, sunny, light-filled Impact Hub offers two private Skype booths. Community-minded, it sponsors events like movie screenings and wellness classes. A co-working space called Bworking offers a program for entrepreneurs that supports startups, the process of business development, and social and humanitarian projects. While another co-working space, called Workup, offers free cycling, walking, and running sessions for health conscious digital nomads.

Portugal has invested a lot in its WiFi infrastructure, with 90% coverage nationwide and an average internet speed of 21 mbps in Lisbon. You can find free WiFi in many of Lisbon’s parks and cafés, and most Airbnb’s will come equipped. But if you want your own landline internet connection, it will cost $20 to $30 a month, depending on speed.

You can rent in Lisbon from approximately $600 a month. However, as a digital nomad, you’ll probably be searching for shorter-term solutions. On Airbnb you can you find one-bedroom apartments in the city for $55 a night off-season, and $90 a night in the height of summer.

Chiang Mai, Thailand


Chiang Mai has long been considered the spiritual home of digital nomads, and is highly recommended for anyone starting out on their remote working journey.

What makes Chiang Mai such an easy starting point is that well before it became a popular digital nomad destination, it was a popular retirement haven for expats from around the world. This means that there is an established Westernized community within the fabric of the city, with plenty of cafés, restaurants, social groups, and entertainment networks for every kind of proclivity—dwarfing the size of most metropolitan digital nomad communities, many times over.

Aside from being low cost, with pleasant temperatures, Chiang Mai offers a more romantic reason for its popularity too. The ancient city, filled with temples and historic treasures, melds comfortably with the sprawling modern metropolis that has built up around it. It has a laidback atmosphere, and, it feels more like a sleepy country town than a chaotic city.

Canadian digital nomad Shikha Dhawan was once a marketing manager of a niche software company working 10-hour days. She recalls, “I was working intensely and not taking care of myself. I realized that I needed to create balance in my life. I just wasn’t happy. I wanted something different.

“Because everyone pretends to be happy with a conservative life, you think you are crazy for not being happy. I’d say to myself ‘Why am I still unhappy when I make good money and I can buy what I like?’ It just wasn’t right for me.” A $70,000 annual income was not enough to keep Shikha in the country that she grew up in.

Shikha decided to do research before she came to Chiang Mai. “There were three places I was interested in: Budapest, Hungary; Medellín, Colombia; and Chiang Mai, Thailand. Ultimately, I chose Chiang Mai. I love Asia, and I was looking to expand my travel repertoire. Chiang Mai has very welcoming nomad groups, I just post on the Facebook page and all my questions get answered. The community are so kind and so giving, and I love that. There are a lot of groups that meet face to face too. I’m even doing an improv course at the moment. I also love street food.”

Shikha’s costs are minimal compared with her costs of living in Canada. To survive in her city of Toronto, she would need at least $5,000 per month to pay living expenses. In Chiang Mai, however, things are very different. Not only can digital nomads save thousands per month while living in Chiang Mai, they compromise on nothing in terms of lifestyle experiences. Her rent is $500 a month, she pays $20 a month for internet, $200 (maximum) on food, $13 on water bills, $20 on electricity, $200 on business expenses, and $100 on a personal assistant—allowing Shikha to work just 10 hours per week while she builds her health and wellbeing business, The Millionaire Hippy.

Internet speeds in Chiang Mai are fast and services are cheap. You also have access to the massive amount of WiFi hotspots all over the city—to the point where you’re rarely without a connection as you walk the streets.

However you really don’t need to worry about internet if you’re planning on using a co-working space, and at the prices available in Chiang Mai, you really should. To give you an example, at a co-working space called Addicted to Work, you can rent a desk by the hour for 63 cents, or for eight hours for just $3.75 (including one drink). Monthly co-working passes rarely exceed $100, and most spaces are open 24/7.

Mexico City, Mexico


Mexico City shares a similar story to Medellín, in that it has entirely regenerated as a city in recent years, becoming one of the most powerful cultural and economic hubs in Latin American.

At over 573 square miles, the city feels massive, but most expats and digital nomads—as well as the capital’s 1,200-plus startups—tend to congregate in just a few central districts.

“There’s an ease to moving about the city, it’s very inviting and nomad-friendly,” says Karina Cobb, a business consultant currently working remotely in Mexico City. “I am enjoying how walkable the neighborhoods of Roma and Condesa are, all the green spaces, parks, and avenues, and how easy it is to find a co-working space or coffee shop to sit and work from.”

Colonias Juarez, Condesa, Roma, San Rafael, St. Maria de Ribera, and Polanco are all within walking distance from the city’s incredible museums, parks, and monuments. Nightlife is electric, from dance clubs to underground jazz bars and salsa dives. But also within these buzzing districts, startup activity is attracting many local meetups, big name conferences, recognized accelerators, and a community of co-working spaces.

The international co-working brand WeWork has six locations here (costing about $160 a month for a hot desk)—monster spaces with hundreds of shoulder rubbing opportunities with other freelancers and entrepreneurs. Smaller co-working spaces like a.255 Social Working Club in Condesa (starting at $250 a month) or Impact Hub (starts at $145 a month) in Roma, come in more intimate sizes.

Amy Martyn, a freelance writer who used a co-working space called We are Todos in Roma, says that she was the only American using the space, but everyone made her feel welcome. “There were all sorts of creative things going on. One person was starting a sewing business, others were working in digital media.”

Internet speed here is excellent and available in most coffee shops and businesses. Even though there is no free citywide system, you can get WiFi in many of the central parks and several lines of the metro.

The city is also extremely affordable. In Colonias, Roma, and Condesa (three of the most popular for visitors) average rent is $500 to $900 a month. Airbnb has meant lots of great spaces have opened up that allow temporary residents to really dig into neighborhoods and the city.

Food in restaurants, on the street, and in the markets, is relatively inexpensive and you can find products and cuisines from across the country and around the world. A remote worker can easily live in Mexico City on $2,000 a month and that includes everything: rent, food, utilities, and transportation.

Sharing a time zone with the U.S. makes it easy to do business remotely, and Mexico City is just a quick, inexpensive trip for a meeting, conference, or to visit family or friends. As a major travel hub, it’s also an ideal place to base yourself for visiting the rest of Latin America.

Tallinn, Estonia


The beauty of being a digital nomad is that you don’t have to find that perfect forever destination. You can go to Berlin for the nightlife, Paris for the cafés, or Bali for the surfing, enjoying all of their best qualities without having to settle for any of them. Because you’re never tied down to one place, you can enjoy a destination when the weather is good, then travel to the other side of the world when it starts to turn wintery. And certainly for this next location you’ll need to time it right.

Tallinn, Estonia is not a year-round destination. Winter temperatures can fall as low as -20 F, with heavy snow. Summers are milder, reaching the mid70s F. But what it lacks in climate, it makes up for elsewhere.

What Tallinn offers above all else is a glimpse of the future for digital nomads. In Estonia, internet access is enshrined as a human right and everything happens online. With the second fastest public WiFi in the world (next only to its Eastern European neighbor, Lithuania), citizens can vote, secure mortgages, open bank accounts, and even open businesses in minutes, without ever leaving their café table.

Recently, Estonia announced the first official visa for digital nomads. The permit will entitle nomads to 365 days of working in Estonia, including 90 days’ travel in the Schengen area. They have also created an e-residency program, making it possible to start an EU-based company online.

By all accounts, Estonia is creating the framework for the new digital nomad world, and Tallinn is at the heart of it.

Garrett Oden and his wife, Lauren, made Tallinn their first stop on their digital nomad adventure once they realized that they could earn from anywhere while freelancing. “We wanted to start somewhere that was affordable, somewhat familiar Western cultural norms, and was still a bit off the beaten path. Tallinn seemed perfect for a month-long stay in August,” says Garrett.

“The city has approximately 500,000 people, but despite its size, Tallinn actually feels small and quiet. The streets aren’t jammed with traffic, calm green parks were everywhere, and even in one of the most busy intersections, at the crossroads of old town and the modern tech town, Hobujaama, you never feel like you’re in a large city. Tallinn is very pedestrian-friendly. There are countless tree-lined paths and forest walkways throughout the city.

“The city has a stunning blend of modern, soviet brutalist, and ancient architecture,” says Garrett. “But old town, the most fascinating area of Tallinn features colorful, fairytale-esque buildings, all smashed close to each other, lined by cobblestone streets.

“Restaurant food is typically $8 to $15 per meal. A comfortable and modern Airbnb on the edge of town is $800 for the month. An Uber costs just $3 to $6 for a ride into downtown. The city bus system was also affordable, at $30 for the month, and very pleasant to use—the most pleasant buses we’ve ever used.

As a growing tech hub, Tallinn doesn’t disappoint when it comes to internet and remote working infrastructure. “The internet speed in our Airbnb was incredible, and we easily found WiFi in restaurants, coffee shops (so many great ones), and even throughout one of the most beautiful parks I’ve ever seen—Kadriorg Park,” says Garrett.

For anyone attempting to turn a business idea into reality, there is hardly a better environment in the world. Local accelerators include Startup Wise Guys, Elevator Startups, and Buildit while other top incubators include TÜ Ideelabor and Startup Incubator. Coworking spaces dot the city, with hot desks available from about $6 per day or $106 per month.

“The nomad community was definitely smaller in Tallinn compared to other places I visited, like Athens, Greece and Antigua, Guatemala,” says Garrett. “I think that’s changing quickly though—more and more people are learning about the fascinating city of Tallinn, and with their upcoming ‘nomad visa,’ the city will probably see far more nomad visitors.”

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