- Tayler Gill spent a month in 2022 with a remote-work program in Ponta do Sol, Portugal.
- Ponta do Sol has a population of fewer than 9,000, and is encouraging remote workers to move there.
Tayler Gill started working abroad in May 2018, when she spent 11 months bouncing around New Zealand house sitting while on a working holiday visa.
It gave her the taste for life abroad. Since then, the 35 year old has worked from Australia, Bali, Vietnam, South Korea, France, Switzerland, and the United Kingdom, while building her business as a digital nomad coach. In the role, she helps others transition from working in an office to working from destinations across the globe, as she has.
The digital nomad community has grown in tandem with the rise of remote work. Almost 17 million Americans described themselves as digital nomads in 2022. That's a 9% increase from 2021, and a 131% increase from 2019, according to a MBO Partners' 2022 State of Independence study of more than 6,000 US adults.
Opportunities available to digital nomads have grown in that time, too.
Gill took a job with Hacker Paradise, a travel company that organizes extended group trips for remote workers, as a community facilitator and operations associate in 2021.
In June 2022, she had the opportunity to travel with the company and about 20 other avowed remote workers to the Digital Nomad Village in Ponta do Sol on the island of Madeira in Portugal, about a 2 1/2-hour ferry ride from the mainland.
Gill said her trip was paid for by the company, as she was an employee, but people opting into the experience paid about $2,800 for the month-long stay, including housing.
The Digital Nomad Village was established in February 2021 by the Regional Government of Madeira through Startup Madeira. Its goal is to attract remote workers to Madeira with its "natural beauty, activities in nature, culture, and fantastic climatic conditions throughout the year," according to Startup Madeira.
"By the time we got there, the Digital Nomad Village was already pretty established," Gill told Insider. "Their whole thing was to build a community and foster that community for digital nomads coming in."
It's easy for the village's digital nomads to socialize with each other
Ponta do Sol's Digital Nomad Village isn't just a perch in the sun for folks with laptops.
The village provides support for people choosing to work remotely from there, including a free-to-use coworking space with desks, chairs, and strong WiFi.
"The weather was super nice, so the doors on the patio were always open and there were outdoor spaces in the shade or the sun that you could also sit and work," Gill said. "Everything inside was completely silent. There was no talking, but you could step outside and talk and work and socialize out there."
The community's active Slack, an instant messaging platform for groups, was another perk of the village. Gill said it was the place to check for adventures outside of work.
Activities included mindfulness exercises, scuba diving, hikes, and other ventures exploring the roughly 17-square-mile municipality as well as neighboring cities like Funchal, the capital city of the Madeira archipelago that's about a 30-minute drive away.
"One of my absolute favorite hikes I've ever been on was this sunrise hike at the very top of the tallest mountain on the island," Gill said. "You watched the sun rise over the clouds and then you hike through the clouds to this other mountaintop."
It isn't as easy to make a connection with the locals
Most digital nomads travel solo, Gill said, adding that the best way to meet people is through traveling groups, like Hacker Paradise.
While Gill was able to meet other Americans, Europeans, and Australians during her stay, she said it wasn't as easy to meet locals. And the tightly knit digital-nomad community that already existed in Ponta do Sol made it even more difficult to hang outside the group.
Gill's wisdom for other traveling workers: You have to make an effort to meet locals — it won't just happen.
"I think that was definitely an issue for us," Gill said. "Not only were we part of our own group program" with Hacker Paradise, "but then you also have the digital nomad program, which is just another step removed from the locals."
Ponta do Sol is tiny, and only has about 8,200 inhabitants. Gill often ran into the same people, but because of the group dynamics it was hard to intermingle.
"You do see those same workers over and over, but we weren't becoming friends with them or hanging out with them outside of work," she said. "No matter what city you're in and where you go, you have to make an effort to do things that locals do and be where locals are."
Have you worked remotely in a different country and had a unique experience? Tell us about some of your experiences traveling while working. Email reporter Jordan Pandy at jpandy@insider.com to share your story.