Episode 115

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Published on:

14th Apr 2026

115: Boundless Life in Uruguay: Week 1 in La Barra - Family Worldschool Adventure

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.

✨ In This Episode:

  • 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

📍 About Boundless Life

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

🏄‍♀️ Why We Chose La Barra, Uruguay

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

🌴 First Impressions

La Barra feels like:

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

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

💡 Tips If You're Considering This

  • 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

📅 What’s Coming Next

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

💬 Let’s Connect

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

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About the Podcast

Transform With Travel: Trip Planning Made Easy For Busy Professionals Craving Bucket List Adventures
Are you sitting behind your desk craving an adventure to make you feel alive again? But with thousands of travel options out there, where do you begin?

Transform With Travel is designed for busy professionals who want more bucket lists trips that reignite adventure, go beneath the surface and feel unique to you WITHOUT the overwhelm of planning, the endless midnight scroll and the crowded tourist traps.

About your host

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Kelly Tolliday

Kelly is the Founder of Transform With Travel, with over 11 years in the travel industry. She's a Wellness Travel Expert, Retreat Facilitator, Travel Advisor & Podcast Host.

She's also a 500-Hr Registered Yoga Teacher & an Accredited Continued Education Provider for the Yoga Industry.

She's traveled to over 45 countries and lived across 4 continents. Now, it's her mission to inspire and support you in stepping outside of your comfort zone and into the life of your dreams.

She's passionate about immersive and transformational travel. She believe when you travel with intention, by combining wellness, adventure & cultural enrichment, you can truly transform your life, one trip at a time.

She's now based in South Florida, and she's married to her husband Sam with 2 beautiful daughters & 2 crazy dogs.