In this deeply personal episode of Transform With Travel, Kelly Tolliday shares the emotional rollercoaster of weeks 4 - 6 in La Barra, Uruguay with Boundless Life.

What started as an exciting worldschooling adventure quickly turned into a crash course in the realities of living overseas — navigating injuries, grief, missing major family milestones back home, extreme weather, and the emotional complexity of leaving behind a strong village in Florida.

But through every hard moment, one thing became crystal clear: the power of community.

Kelly opens up about:

• Missing family milestones and family loss
• Multiple surfing and back injuries
• Why having a built-in village through Boundless Life changed everything
• The unexpected transformation that happens when you allow new people into your life overseas

This episode is an honest look at what people don’t always talk about when it comes to worldschooling, family travel, and relocating abroad: life doesn’t pause just because you move somewhere beautiful.

And yet… even through the hard moments, there’s still magic in slowing down, watching the ocean every day, and creating a life that feels deeply aligned.

• Why Kelly’s family chose Uruguay for their first Boundless Life program
• The emotional reality of leaving a strong support system at home
• Building deep friendships quickly while living abroad
• The “week 4 slump” many families experience during long-term travel
• How the Boundless Life community became a true support network
• Why village and community matter more than location
• Reflections on parenting, identity, and personal growth overseas
• Surfing injuries, SI joint rehab, and navigating healthcare abroad
• Mid-cohort travel to Punta del Diablo & Santa Teresa National Park
• The beauty and difficulty of creating a life outside your comfort zone

• Boundless Life
• La Barra, Uruguay
• Workschooling
• Episode #55: Parenting Across Cultures with Elodie Fourchaud

If you’re considering a Boundless Life program and want to ask questions about Kelly’s experience, feel free to reach out.

Use code KELTOL11 for €400 off your first program.

(And yes — Kelly shares transparently that she also receives a future program credit if you use the code.)

• Podcast: Transform With Travel
• Instagram: @kelly.tolliday
• Follow the family’s Uruguay & worldschooling journey for more honest reflections on travel, parenting, surf life, and building community abroad :)

I’m back with another update from our family’s adventure in La Barra, Uruguay with Boundless Life 🌎

In this episode, I’m sharing what the past couple of weeks have really looked like—from settling into school and coworking life, to sneaking away for a wedding in Argentina, to the unexpected things that have surprised me (hello… mosquitoes 😅).

If you’ve been curious about worldschooling, slow travel with kids, or what daily life actually feels like inside a Boundless Life program… this one’s for you.

Thinking about Boundless Life for your family? Use my code KELTOL11 for a discount on your first program with Boundless Life

• What the welcome week experience looks like for families
• Inside the school + coworking setup (and how it actually flows day-to-day)
• Our quick trip to Mendoza for a wedding (with kids!)
• How the kids adjusted to school + extracurriculars (surfing, art, cooking 🎨🌊)
• What parent life looks like (coworking, community, social events)
• The magic of being surrounded by 18 like-minded families from around the world
• My honest take: is Boundless Life too good to be true?
• Learning Spanish in Uruguay (and why it’s actually easier here)
• The BIG surprise… the mosquito situation 🦟
• Practical tips: getting around, cost of living, and what to expect

• This experience feels like life slowed down—in the best way
• The community aspect has been one of the biggest unexpected wins
• Uruguay is not a “cheap” destination—but it does feel safe, calm, and easy to live in
• If you want to truly learn Spanish… this is the place

• A car or e-bike will make your life much easier
• Expect cost of living similar to the U.S. (especially groceries + dining)
• Take advantage of nearby gems like Portal Bosque and surrounding beach towns
• Pack (a lot of) bug spray

There’s this rhythm here that just works—surf in the morning, work during the day, community and connection woven throughout. It feels full, aligned, and honestly… how life is meant to be lived.

Use my code KELTOL11 for a discount on your first program with Boundless Life

Have questions about worldschooling, Uruguay, or Boundless Life? Drop them in the comments or reach out—I’m happy to share more 💬

Thinking about worldschooling with your family? Curious what life is actually like in Uruguay? This is your real, unfiltered Week 1 update from our 3-month adventure with Boundless Life in La Barra.

I’m taking you behind the scenes of our experience—from the chaos of preparing to leave, to first impressions of this dreamy surf town, to what it actually feels like to land in a brand new country with kids, work, and zero routine.

If you’ve been Googling, YouTubing, and trying to piece together what Boundless Life is really like (same 🙋‍♀️)… this series is for you.

• What Boundless Life is (think: study abroad… but for families)
• Why we chose Uruguay over Europe, Bali, or Japan
• Traveling from Florida → Montevideo → La Barra
• The real prep process (spoiler: it’s a lot 😅)
• Renting out our home + what we wish we knew
• Traveling with dogs (and what we did instead 🐾)
• First impressions of La Barra (Bali + Australia + California vibes 👀)
• Our first week exploring: beaches, forests, surf, and nearby towns

Boundless Life is a global worldschooling program for families:

• 🌍 8 locations around the world
• 🏡 Fully set up homes or apartments
• 🎓 Education center for kids (18 months–teens)
• 💻 Co-working spaces for remote-working parents
• 🤝 Built-in community of like-minded families

👉 Learn more: https://boundless.life

💸 Use code KELTOL11 for €400 off your next program

• Closer to Eastern Time Zone for work
• Spanish immersion for our family
• Surf + beach lifestyle 🌊
• Slower, more peaceful destination

La Barra feels like:

• Bali (Canggu vibes)
• Australia (Byron Bay / Bondi energy)
• California coastlines

All wrapped into one relaxed, beautiful, under-the-radar destination.

• Start preparing your home WAY earlier than you think
• Give yourself grace—the final month is intense
• Arrive a few days (or a week!) early to settle in
• Expect things to take longer than planned—and that’s okay

• First week of school with Boundless Life
• Co-working space review
• Daily routines + family rhythm
• More local exploring

Have questions about Boundless Life or Uruguay? Drop them in the comments—I’m sharing everything I wish I knew before booking.

👍 If this helped you, like & subscribe for weekly updates from Uruguay!

💸 Ready to be Boundless? Use code KELTOL11 for €400 off your next program