How to Be a Digital Nomad Family and Travel Around the World With Kids

Shirly and Erez Weinstein had in many ways achieved the American dream. They immigrated to

Shirly and Erez Weinstein had in many ways achieved the American dream. They immigrated to the United States from Israel in the early aughts, bought a house in the suburbs of Atlanta with access to high-quality public schools for their two kids, and excelled in their tech careers. There was just one problem: They weren’t happy.

“Our life was just really busy,” Shirly Weinstein told me. “Work, school, after-school — we hardly had any down time or time as a family.”

They also weren’t satisfied with the education options for their kids. “We wanted something more from school,” Erez Weinstein said. “We tried Montessori, charter, public, but all these different options felt like more of the same.”

The kids felt similarly. “Life was boring,” Ella, their 11-year-old daughter, told me. So, to shake things up, in 2018 the family sold most of their possessions, bought an RV, and started traveling full time around the US and abroad while homeschooling.

For the next four years, the kids did not attend formal classes, instead learning from their experiences in different countries, and did occasional academic work on digital platforms like Khan Academy. Then, in 2022, the family learned about Boundless Life, a startup trying to build a global network for digital-nomad families, complete with built-in community, project-based education, and furnished homes where families live for three months at a time.

While the phrase “digital nomad” might conjure an image of a single 27-year-old software engineer writing code from a hostel in Chiang Mai, Thailand, Boundless Life — which has locations in Portugal, Indonesia, Italy, and Greece — targets a different demographic of long-term travelers: parents and their elementary-school-age children. The startup’s aim, according to its cofounder Mauro Repacci, is to allow parents “the freedom to travel as a single person might, but with your kids.”

Boundless Life is one of a handful of programs — like the Green School in Bali and The Hive in the Dominican Republic — that cater primarily to international students and their remote-working parents. While there isn’t great data on it, experts I spoke with say that only a small fraction of the estimated 35 million global digital nomads are traveling with children — which makes sense. Whether figuring out school or supporting kids’ ability to maintain lasting friendships, many parents are wary of uprooting their families’ lives for long-term travel.

But with the growth of remote work and newfound energy to reimagine education in response to the coronavirus pandemic, businesses are jumping at the opportunity to make “nomading” with children a real possibility.


Last summer I visited the Boundless campus in Sintra, Portugal. When I arrived by train from Lisbon, it was easy to see why the company had chosen the medieval mountain town as its pilot location. The Moorish castles and orange clay roofs give the town a classic European charm, and it has just the right amount of creature comforts and English-speaking waitstaff to please less adventurous travelers. At just shy of 400,000 inhabitants, Sintra is also big enough to absorb the 25 Boundless families without the expats dominating all the local haunts. 

A chef preparing a meal in a kitchen with a mosaic tile floor.

At school, kids are fed organic meals made by a local chef.

Simone Stolzoff



The Boundless community, which includes families from around the world, felt a bit like a family camp. Families each had their own private accommodations scattered throughout the city, but they frequently spent time at one another’s apartments for meals and aperitifs. Parents went out for afternoon espressos and lingered at school drop-off to chat about business opportunities before heading to a mosaic-tiled coworking space replete with WiFi and Portuguese custard tarts.

In the school, a remodeled two-story building blocks away from Sintra’s castles, mixed-aged groups of students hunched over tubs of water to learn about density and volume. For lunch, the kids ate organic meals provided by a local chef. After school, kids from different families entertained themselves in the cobblestone streets and parks under light adult supervision. 

Tim, a freelance computer programmer from Ohio, joined Boundless in 2022 after taking his kids out of school at the start of COVID. “The school said ‘Zoom Kindergarten,’ and I said screw that,” he told me.

One couple from Seattle — Edward, a marketing consultant, and Jessica, an entrepreneur — not only pulled their four kids under 13 out of school to sign on with Boundless Life, but they also persuaded another family to join them for the experiment. “We wanted to travel, but you can’t babysit a 1-year-old and homeschool a 7-year-old at the same time,” Jessica said. “Education was the question. If we could figure out the education piece, the rest would fall into place.”

According to Boundless’ cofounder and head of education, Rekha Magon, Boundless’ vision is for families to hop to Sintra for a semester and then to Italy’s Tuscany region for another, all while their children progress through the same curriculum, which extends from preschool to age 12. “Education should be removed from a single building and exist in the world,” she told me. 

I’ve had more social interactions in the past week than months back home — and I didn’t have to send a single email to coordinate.

This was perfect for the Weinsteins, who consider themselves part of the worldschooling movement — a growing community of families who have decided to eschew traditional education in favor of long-term travel and “learning from the school of life,” as Erez Weinstein told me.

Compared with all the education options they had tried in Atlanta, Boundless was the first school that seemed to align with their desire for project-based learning with a global perspective. “If Boundless had locations all over the world, we would be set,” Shirly Weinstein said. “It’s beyond travel. It’s experiencing the world.” 

And while the kids seemed to be thriving, perhaps the true beneficiaries were the parents. As one Boundless parent told me, “I’ve had more social interactions in the past week than months back home — and I didn’t have to send a single email to coordinate.”

Boundless had recreated the village.


As a Brazilian from Montreal with Italian ancestry, Mauro Repacci is a fitting founder for a company that promotes global citizenship. The idea for Boundless came about after Repacci and his cofounder Marcos Carvalho sold their previous company, a home-buying platform called NestReady, and were looking to take a sabbatical. It was the summer of 2021. COVID restrictions were loosening and the built-up demand for travel was palpable.

“During the pandemic, like many people, we started to ask how we wanted to live our life, how we wanted to raise our kids,” Repacci told me. “And we felt like we were limiting ourselves by staying in the same country for a long time.” He added, “We felt something was missing.” He started to tell friends about his aspiration to travel and take time off — perhaps a few months in Costa Rica, another few in Europe or Southeast Asia. His friends were intrigued by the idea of long-term travel but had hesitations about their kids falling behind in school.

Sintra portugal

The Boundless founders chose the medieval mountain town of Sintra, Portugal as their first location.

Rolf E. Staerk/Shutterstock



Repacci and Carvalho started a WhatsApp group with dozens of friends and friends of friends who were all trying to figure out how to make long-term travel work with kids. They researched international schools and looked into the feasibility of hiring a private tutor to travel with them full time. Their brainstorming quickly transformed into a business idea. 

According to Lona Alia, the head of revenue for the nomad-travel-insurance provider SafetyWing, several factors have led to the growth of digital-nomad families. “There’s remote work, the availability of high-speed internet, flexible schooling, and Airbnb,” Alia, who is part of a digital-nomad family herself, told me. But perhaps the biggest factor is a cultural shift toward the value of experiences, Alia said. “Many people are realizing that the traditional path of acquiring material goods isn’t necessarily the key to happiness, and are instead choosing to invest in experiences, such as travel.”

For the Boundless founders, figuring out the education piece of the puzzle was key. For families to actually be able to make the leap, Boundless would need a curriculum that was rigorous enough to adhere to parents’ standards and flexible enough so families could bounce between locales without their kids falling behind. To solve the problem, Repacci and Carvalho brought on their head of education, Magon, and head of brand and product, Elina Zois. 

Boundless decided to base its educational model on the Nordic Baccalaureate, an interdisciplinary curriculum based on the Finnish education system that emphasizes project-based work, experiential learning, and cultural immersion. Classrooms are multiage and class sizes are kept small — fewer than 15 kids a class for students under 6 and fewer than 18 for those ages 6 to 12. During my visit, the school felt like a more expansive definition of what an education could be. Learning was not limited by the four walls of the classroom — it took place in parks, pottery studios, restaurants, and museums.  

Several educators I spoke with were skeptical about how the Boundless framework would translate into meaningful learning experiences for students from a range of academic needs, and how students would be able to integrate their Boundless experience if they transitioned back into more traditional school environments.

An outdoor play area

Learning at Boundless was not limited by the four walls of the classroom.

Simone Stolzoff



But parents I met told me Boundless had sparked a level of intellectual curiosity in its children that spilled over to “normal life” upon returning stateside. “Getting to try out a different type of school was life-changing,” one parent said. After returning to US public school this year, they said their kids were doing better than they had before doing Boundless. “Not because anything is better at their school this year than last year, but because they are different,” the parent said.

The company serves about 85 families and 250 kids during any given semester. But despite some early success, Boundless Education, like the organization itself, is still very much a startup. The school isn’t accredited — though it’s undergoing the accreditation process — and the administration is still figuring out the kinks, like how to quantitatively measure student growth and how to cater to older and more advanced students’ needs.

There are also financial and cultural barriers to joining Boundless. For one, there’s the price. It costs the equivalent of about $1,600 a child, a month, to take part in Boundless Education, and the equivalent of $460 a parent, a month, for coworking and concierge services — and that doesn’t include the cost of housing. Though participants were relatively diverse racially and culturally, most of the families I met in Sintra were high earners from North America.

Plus, there are cultural and logistical challenges to picking up your family and living around the world for months at a time. Boundless advises families on how to obtain digital-nomad visas for countries that offer them, but the prospect of working abroad long term can be challenging depending on your country of origin. 

“The biggest barriers to more people nomading are in-laws, grandparents, and a lack of imagination,” Andreas Wil Gerdes, a leader in the worldschooling movement, said. “For 200 years, the majority of people have lived in a work-centric model of existence. Finally, people are going back to a life-centric model, but it will take time to catch on.”

Gerdes is generally supportive of Boundless’ mission but commented that the company served a limited slice of those who might be able to benefit from living and learning abroad. “Boundless is the brain-dead solution for people who don’t want to have to make any decisions,” he said. “But it’s a step in the right direction.”


On my last night in Sintra, the Boundless families gathered together at Praia de Maçãs, a beach 20 minutes from downtown. Kids dashed in and out of the waves, occasionally running to shore to grab a snack or tug at their parents’ trunks. “How long have you guys known each other?” I asked a few preteens who were building castles in the sand. “I dunno. A few days,” one said, barely looking up.

Standing there on the edge of the European continent, I realized that although Boundless is cloaked in the sheen of a venture-backed startup, the business is actually a return to a more collective form of child-rearing. Sure, there’s an app that parents use to interact, a curriculum that uses the UN sustainability goals for lesson plans, and a business model that’s a response to a global workforce trend. But as I immersed myself in this network of families who were loosely looking after one another’s children, Boundless felt more retro-chic than modern. 

I came to Sintra thinking Boundless might be too good to be true, but perhaps that was a failure of my own imagination.

After leaving the beach, I joined the families for pizza at an outdoor restaurant. There were no iPads at the dinner table or calendar invites needed to organize the get-together. In a community full of families, conversations were not dominated by talk of academic tutors and afterschool programs. Everyone seemed to be enjoying themselves. 

I came to Sintra thinking Boundless might be too good to be true, but perhaps that was a failure of my own imagination. Maybe I, like so many others, am still too attached to the idea that school ought to look like 20 students facing the same way in a classroom for seven hours a day. Sure, Boundless is an expensive, turn-key study-abroad experience for elementary-school-age children and their parents, but it’s also a refreshing take on what it means to give a child an education, which, especially in America, is in need of a refresh.

Certainly there are risks of uprooting children from their routines and communities. Programs like Boundless may not be attractive or accessible to everyone, and it’s unclear whether Boundless will be able to scale its programming to meet the growing demand. But when I think about the atomization of our modern lives, each of us cordoned off in our little boxes made of ticky-tack, learning from textbooks and digital apps, I see Boundless as a welcome alternative. Perhaps the world is the classroom we’ve been waiting for.


Simone Stolzoff is a writer and author from San Francisco. His debut book, The Good Enough Job: Reclaiming Life from Work, was published by Penguin Random House earlier this year.