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Traveling as a family of six might sound crazy – as mom Jessica Webster cheerfully puts it, “with four kids, life is bonkers” – but that hasn’t stopped the Webster family from embracing Boundless Life adventures across the world.

Jessica and her husband Ed have four children (now ages 10, 8, 7, and 3). They’re a big family unit with a lot of littles!

Since joining Boundless Life in 2022, the Websters have experienced Boundless Life in Portugal, Greece, and Montenegro, and are now gearing up for their first ever 3-month cohort in Spain.

Along the way, they’ve figured out creative solutions to make a “Boundless” life and travel feasible for a large family – from budget hacks to safety plans and travel tricks – all the while keeping their sanity.

In this family profile, we highlight how Jessica’s crew makes Boundless Life work for them. If you’re wondering how to handle housing, transportation, safety, and fun for a big family abroad, their experience offers plenty of helpful tips. Jessica’s advice shows that with flexibility and planning, even a bonkers big family can live the travel digital nomad life.

How a Change in Schooling Has Lead to a New Opportunity

The Webster family's approach to Boundless Life evolved naturally. Initially, they were limited to summer getaways, due to the school's attendance policies. However, a move to Texas and a new school that was supportive of their family's travel goals, has ultimately opened up a world of new possibilities.

Their current educational setup allows them the best of both worlds: traditional schooling's structure, combined with Boundless Life's enriching global perspective. Jessica admits the arrangement involves a bit of logistical juggling, but it's exactly what their family is seeking to thrive both at home and abroad.

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Remote Work and Travel

Jessica and Ed both manage their careers remotely. Jessica runs her own business Little Stints, organizing small-group, family-oriented travel experiences. Her work involves creating end-to-end guided trips in adventurous locations, such as Mexico and Morocco.

Ed, meanwhile, consults for private equity firms and manages various projects remotely, including writing and podcasting.

Together their remote jobs which they’ve created for themselves, allow the entire family the flexibility to maintain their global adventures without compromising their professional lives.

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Freedom From Overscheduling

Jessica loves how Boundless removes the stress of overscheduling that’s common back home. “I’m not driving the kids all over everywhere – or saying “no” to playdates because I can’t get the kids there,” she says.

With most activities at the Education Center or within walking distance, the kids can make their own choices and even walk to a friend’s house independently. “The answer is almost always yes, go!” Jessica explains. This freedom gives the children independence while giving parents more breathing room and one-on-one time with their kids. “And I’m not stuck in a car. Everyone wins.”

Multi-Generational Memories

Another highlight for the Websters has been inviting grandparents to share the Boundless experience. Jessica explains how her parents joined them in Sintra as part of the founding families. They’re “exploring the world with the grandkids, making global memories, learning together about new places, cultures and food.” She adds, they’ll soon join again in Spain.

For Jessica, this is one of the most special parts of Boundless: the chance for kids and grandparents to connect deeply while discovering a new place together.

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Money-Saving Tips for a Family of Six

One of the Webster family’s biggest challenges, as with any large family, is budgeting for travel. As Jessica acknowledges, once you add up accommodation, flights, school fees, and daily expenses for four kids, “it all adds up.”

Instead of walking away from the opportunity of travel, the Websters found smart ways to experience Boundless Life and to make the budget go even further. Here they kindly share some of their key money-saving strategies.

Creative Approaches to Housing

With four children, the Websters have learned to think creatively about housing arrangements during their Boundless stays.

Jessica explains the need to embrace flexibility as a family. For example, in their last cohort they took a smaller apartment and the four children shared one room. They’ve also had their children sharing travel cribs. It’s just about thinking outside the box and keeping a relaxed approach to sleep routines and configurations, which as a result also means their children become further adaptable to new situations.

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Bring Your Own Childcare

With four young kids, and juggling remote work commitments, an extra set of hands is vital. The Websters occasionally bring an au pair along on their travels. This is a win-win as the kids have a familiar caregiver, and Jessica and Ed have reliable support without breaking the bank. By traveling with an au pair, they get ample childcare and even enjoy quality one-on-one outings and activities with their children.

DIY Activities and Local Fun

Boundless Life offers wonderful excursions and extracurriculars, but for a large family those fees multiply quickly. The Websters learned to hunt out experiences on their own, discovering cheap or even free opportunities, enabling further connection into everyday local life, culture and community.

These budget-conscious choices mean the Websters can invest in what matters, like travel and education, without feeling pinched. Small savings add up when multiplied by four children. As Jessica’s experience shows, don’t be afraid to look for alternatives – whether it’s housing, childcare, or activities – that fit your family’s size and budget.

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On the Road: Transportation Hacks for Large Families

Getting a big family from point A to B, C and beyond, is no small feat. The Websters have experimented with various transportation strategies and seem to have the formula down packed. Here are some of their recommended tips.

Pack Portable Safety Gear

Jessica admits she’s a stickler for car seat safety. But “there’s no way in the world we could schlep around three car seats,” she points out. Their solution was to use foldable travel car seat vests for the older kids.

These vests, such as the Ride Safer, are U.S. safety approved and pack down small enough to fit in a backpack. The kids simply wear the vest and buckle in with a normal seatbelt, safe and sound.

For their youngest, who was just a baby at the time, they carried a lightweight “bucket” infant car seat, since it clicks easily in and out of taxis. With this setup, the family can hop into an Uber or taxi anywhere without lugging bulky car seats wherever they go.

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Strollers, Carriers… or Both

When it comes to moving little ones around foreign towns, Jessica emphasizes knowing your destination and your children. Sometimes a stroller is a lifesaver while other times it’s unnecessary.

For instance, in hilly Syros, Greece, “it is almost pointless to have a stroller,” she notes – the cobblestone lanes and stairs meant their stroller mostly got used for grocery runs.

Her advice, plan your approach (stroller, backpack carrier, or both) based on the locale and your child’s ability. During one cohort, the Websters brought a double stroller – when their kids were ages 1, 4, 5, and 6, they “definitely had times where all four were in that stroller!”

In other words, evaluate what gear will keep you mobile (and sane), and be ready to adjust as your children grow.

Rethink Car Rentals

Interestingly, the Websters have never rented a car during Boundless Life cohorts. Instead, they’ve relied on walking, public transit, and rideshare options.

In many European cities, renting a huge vehicle isn’t practical or necessary. Jessica says they’ve had good experiences using ride-share services when needed. “We have found Uber XL – in Spain and in Greece – those will fit our family.” By using an Uber or taxi van for the occasional trip, they avoid the hassle and cost of renting a minivan for months. Daily life in Boundless locations also tend to be walkable, so ultimately rental vehicles would become an unnecessary expense.

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Staying Safe and Healthy Abroad

Safety is a top concern for any parent considering world travel. It’s a perfectly normal concern to have reservations about healthcare and emergencies practices in foreign countries. But the Webster family’s experiences have been very reassuring, and Jessica has practical tips to help families feel secure.

Have a Medical Game Plan

Before arriving in a new country, Jessica suggests noting down the nearest hospital or clinic. “Have a sense for where the emergency rooms are, which one you would go to – good first step,” she advises.

The Websters unfortunately did have a couple of medical incidents on the road, but because they knew where to go, they handled each swiftly. In one case, their toddler’s fingers got caught in a door in Portugal – every parent’s nightmare.

Yet the outcome was surprisingly positive: “Our experience there was fabulous,” Jessica recalls. The local ER staff spoke English, they treated the injury quickly, and were even apologetic about the cost – which after an X-ray and seeing a specialist came to only about $80 USD total. “In the grand scheme of American healthcare, [that’s] nothing,” she says.

The takeaway for other families: incidents can happen anywhere, but if you do a bit of homework, carry insurance, know your emergency options, you can feel confident that “help is there when you need it,” often far more straightforward than you might expect.

Everyday Safety & Support

Beyond medical needs, the Boundless Life community itself provided a safety net. With staff and other families on site, the Websters never feel alone in handling challenges. For example, Boundless Life coordinators are always ready to help with recommended trusted local services.

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Embracing Flexibility: The Webster Family Travel Philosophy

Perhaps the Webster family’s biggest “secret” to success is flexibility – with schedules, routines, and expectations. Jessica emphasizes that traveling with four children demands letting go of rigid plans and embracing a go-with-the-flow mindset.

Roll with Different Routines

At home, many of us have carefully orchestrated routines. For example – dinner, bath, bedtime at the scheduled time, and each child in their own bed. On the road, the Websters learned to loosen up those routines and it’s made it easier for everyone. “Some parents are very rigid that kids need their own bed and exact bedtime… that makes travel tougher,” Jessica observes.

Instead, they helped their children practice being adaptable sleepers. Embracing flexible bedtimes and nap spots means the family can handle the unpredictable.

Don’t Overplan – Let Kids Lead

Perhaps counterintuitively, doing less can make an experience richer when traveling with young children. Jessica cautions against packing your itinerary too tight. “People sometimes think, if you’re going for a month or a summer, ‘we need to do all the things’… No.” The reality is, the trip becomes about the kids and the family, not checking tourist sites off a list.

With four children ranging from toddler to preteen, the Websters find joy in simple, local activities rather than exhaustive sightseeing. “Be where you are,” Jessica urges – go to the playgrounds, eat ice cream, wander the streets and see what catches their attention.

Don’t feel guilty about skipping famous landmarks if your children are exhausted or uninterested. “What the kids remember is not going to each of the castles in Sintra,” Jessica reminds. And that’s okay! Ultimately children remain engaged and happy, and parents avoid the burnout of trying to see it all.

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Takeaways on Big Family Travel

Every family’s journey is different, but the Webster family shows that there’s no one-size-fits-all approach to a ‘Boundless’ life – even a larger-than-average family can travel and thrive in this lifestyle, crafting a version that works for them.

For Jessica, the effort has been more than worth it. Her children are growing up with confidence and curiosity, and the family has a treasure trove of shared memories from all around the world.

In the end, the Websters’ story is both inspiring and practical. It’s proof that big families can live out big travel adventures – with some creativity, support, and a dash of courage.

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