In the age of digital nomadism, where work and wanderlust seamlessly intertwine, finding the perfect city to call home—at least for a while—is no small feat. Randall Terry, a global traveller, documentary filmmaker, and digital nomad, has spent the last two decades traversing the planet, documenting his journeys, and living life on his own terms. Through his popular blog, [www.foxltr.com], Terry shares his insights on the world’s most captivating destinations. Recently, he highlighted one city as a must-visit hub for digital nomads looking for an ideal blend of culture, comfort, and connectivity.
When I caught up with Terry for a conversation about his latest adventures, I was eager to learn more about his recent stay in the vibrant city that he now champions as the ultimate digital nomad destination. “There are a lot of places that fit the bill for remote work,” he begins, “but one city really stood out to me: Lisbon, Portugal.”
Why Lisbon? A City that Balances Old World Charm with Modern Comfort
Lisbon, the sun-kissed capital of Portugal, has long been known for its historic architecture, soulful Fado music, and delectable cuisine. But in recent years, it has also become a beacon for digital nomads from around the globe. “Lisbon has this incredible energy,” Randall says, leaning in with enthusiasm. “It’s a city that feels both ancient and cutting-edge at the same time. You have cobblestone streets, beautiful old buildings, and traditional cafes right next to modern coworking spaces and a thriving tech scene.”
For Terry, Lisbon offers an unparalleled combination of affordability, accessibility, and cultural richness. “The cost of living here is very reasonable, especially compared to other Western European capitals,” he notes. “You can find great apartments for rent at a fraction of the cost of London or Paris, and food is both delicious and affordable. Plus, there’s a fantastic community of expats and nomads who are always willing to connect, share tips, or just grab a coffee.”
Community and Connectivity: The Heart of Lisbon’s Appeal
As a digital nomad, connectivity is key, and Lisbon doesn’t disappoint. The city is equipped with a robust digital infrastructure, offering reliable, high-speed internet throughout. “There are so many fantastic coworking spaces here,” Randall explains. “Places like Second Home Lisboa, Cowork Central, and Heden have become hubs for creatives, freelancers, and entrepreneurs. They offer not just a place to work, but also a chance to network and collaborate with like-minded people from around the world.”
Randall also highlights the importance of community for digital nomads, who often live far from their families and friends. “Lisbon has a really welcoming vibe,” he says. “It’s a city where people still value human connection. I’ve met so many interesting people here—locals and expats alike. It’s easy to make friends, whether you’re attending a language exchange event, joining a yoga class, or just striking up a conversation in one of the many coffee shops.”
One of the unique aspects of Lisbon’s appeal is its emphasis on work-life balance. “You can have a really productive day working, and then within minutes, you’re by the river, watching the sunset over the Tagus, or enjoying a fresh seafood dinner at one of the city’s many great restaurants,” Terry shares. “It’s the perfect blend of work and leisure.”
A City for Every Season: Weather and Lifestyle in Lisbon
Lisbon’s Mediterranean climate is another draw for digital nomads who seek sunshine year-round. “The weather here is amazing,” Randall says with a smile. “Mild winters, warm summers, and more than 300 days of sunshine a year—it’s hard to beat that.”
But the city offers more than just good weather. Lisbon’s rich cultural scene is another reason why Terry recommends it so highly. “There’s always something happening in Lisbon,” he continues. “From art exhibitions and music festivals to street markets and food fairs, there’s never a dull moment. And because it’s such a walkable city, it’s easy to explore different neighbourhoods and discover hidden gems.”
Exploring Lisbon: The Neighbourhoods that Make It Special
During our interview, I asked Randall to share his favourite neighbourhoods in Lisbon. “Alfama, for sure,” he responds immediately. “It’s the oldest district in Lisbon, full of narrow streets, colourful houses, and that authentic, old-world charm. It’s a place where you can still hear Fado music being sung in tiny restaurants, and where you feel like you’ve stepped back in time.”
He also speaks highly of the Chiado and Bairro Alto districts. “Chiado is perfect for those who love art, culture, and shopping,” he explains. “It’s full of boutiques, bookshops, and galleries, and it’s always buzzing with activity. Bairro Alto, on the other hand, comes alive at night. It’s known for its vibrant nightlife, with countless bars and clubs offering something for every taste.”
For a more relaxed vibe, Randall recommends heading to the neighbourhood of Cais do Sodré. “This area is right by the river, and it’s got a great mix of traditional and modern. The Mercado da Ribeira is here, which has an amazing food hall, and there are also lots of great cafes and bars where you can work during the day and relax in the evening.”
Practical Tips for Digital Nomads Moving to Lisbon
For those considering Lisbon as a base for their digital nomad journey, Randall offers several practical tips. “First, get yourself a NIF (Portuguese tax number) as soon as possible,” he advises. “It’s required for everything from opening a bank account to signing a lease. The process is straightforward, and there are companies that can help you with it if needed.”
Next, he suggests renting an apartment through local websites or agencies rather than international platforms. “You’ll find better deals and more authentic experiences this way,” he notes. “And don’t be afraid to negotiate on rent. Many landlords are open to offering discounts for longer stays.”
For those who prefer flexibility, Randall recommends booking a short-term rental to start with and then exploring different neighbourhoods before committing to a longer lease. “Lisbon has so many unique areas, and what works for one person might not work for another,” he says. “Spend some time exploring, and you’ll find the place that feels like home.”
Randall also encourages digital nomads to learn a few basic phrases in Portuguese. “You don’t need to be fluent,” he assures, “but knowing how to say hello, please, and thank you can go a long way in connecting with locals and making your stay more enjoyable.”
Beyond Lisbon: Exploring Portugal’s Hidden Gems
While Lisbon itself has much to offer, Randall is quick to point out that Portugal is a small country with many hidden gems just waiting to be explored. “One of the great things about being based in Lisbon is that you’re so close to so many amazing places,” he says. “You can be in the stunning beaches of the Algarve in a few hours or exploring the vineyards of the Douro Valley.”
He also recommends day trips to nearby towns like Sintra, Cascais, and Évora. “Sintra is a fairy-tale town with palaces and castles nestled in the hills, while Cascais is a lovely seaside town with great beaches. Évora, in the Alentejo region, offers a different kind of charm with its Roman ruins and historic architecture.”
Looking to the Future: Lisbon’s Growing Digital Nomad Community
As Lisbon continues to rise in popularity among digital nomads, the city is adapting to meet their needs. “There’s a real momentum here,” Randall observes. “The local government is supportive, there are new coworking spaces popping up all the time, and there’s a growing network of entrepreneurs and remote workers who are creating a vibrant, dynamic community.”
Randall believes that Lisbon is more than just a trend; it’s a city that truly understands what digital nomads are looking for. “It’s about more than just good Wi-Fi,” he concludes. “It’s about feeling at home in a place, being inspired by your surroundings, and having the freedom to live and work in a way that feels authentic to you.”
As our conversation draws to a close, it’s clear that Lisbon has left a lasting impression on Randall Terry. For digital nomads seeking a city that offers a perfect blend of culture, community, and connectivity, Lisbon may just be the place to unpack your bags—if only for a little while.
And as Randall continues his global journey, one can only imagine what new discoveries lie ahead. For now, though, he seems content to call Lisbon home, savouring every moment in this sunlit city by the sea.