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Transform With Travel: Trip Planning Made Easy For Busy Professionals Craving Bucket List Adventures

Transform With Travel: Trip Planning Made Easy For Busy Professionals Craving Bucket List Adventures

Written by: Kelly Tolliday
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About this listen

 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.Copyright 2025 Transform With Travel Hygiene & Healthy Living Self-Help Social Sciences Success Travel Writing & Commentary
Episodes
  • 116. Life in Uruguay 🇺🇾 | Week 2 & 3 with Boundless Life + Honest Thoughts, Surprises & Tips

    116. Life in Uruguay 🇺🇾 | Week 2 & 3 with Boundless Life + Honest Thoughts, Surprises & Tips
    Apr 22 2026

    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

    ✨ In This Episode:
    • 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

    🌊 Real Talk Highlights:
    • 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

    🚗 Helpful Tips if You’re Considering La Barra:
    • 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

    💛 Why We’re Loving It:

    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.

    🎁 Thinking About Boundless Life?

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

    📩 Let’s Connect:

    Have questions about worldschooling, Uruguay, or Boundless Life? Drop them in the comments or reach out—I’m happy to share more 💬
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    17 mins
  • 115: Boundless Life in Uruguay: Week 1 in La Barra - Family Worldschool Adventure

    115: Boundless Life in Uruguay: Week 1 in La Barra - Family Worldschool Adventure
    Apr 14 2026

    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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    13 mins
  • 114: An Intentional Pause, A New Chapter, and Why Time Is the Ultimate Luxury

    114: An Intentional Pause, A New Chapter, and Why Time Is the Ultimate Luxury
    Jan 6 2026
    What happens when the life you’ve been intentionally building asks you to slow down instead of speed up?In the first episode of the year on Transform With Travel, host Kelly Tolliday shares a deeply personal, off-the-cuff conversation about growth, priorities, and choosing presence over productivity.Kelly reflects on nearly two and a half years of hosting the podcast, the lessons learned through travel, storytelling, and connection, and announces a major professional shift into her new role at Travel Kinship, where she now serves as Director of Sales and Marketing. She also shares an exciting family update, spending three months living abroad in Uruguay through Boundless Life, followed by extended travel beyond.With honesty and intention, Kelly explains her decision to place the podcast on pause for a few months, not as an ending, but as a conscious choice to honor time, focus, and family. This episode is a reminder that intentional living sometimes means stepping back, trusting the season you’re in, and knowing when enough truly is enough.You will learn:Why Kelly chose to start the year without vision boards or goal-setting contentHow the podcast shaped her personal and professional growth over the last two and a half yearsWhat a travel representation company does and why Travel Kinship felt like a natural next stepHow ethical, sustainable, adventure-led travel has guided Kelly’s career decisionsWhy her family chose to live abroad in Uruguay with Boundless LifeWhat global living offers children through education, community, and cultural immersionWhy time is the most valuable resource in intentional travel and intentional livingHow to recognize when it’s time to pause something you loveWhy stepping back does not mean stepping away foreverWe talk about:00:00 Intro 01:00 Reflecting on two and a half years of podcasting02:00 Gratitude for listeners and the growth of the show03:00 Announcing Kelly’s role at Travel Kinship04:00 What travel representation companies do05:00 Why working with on-the-ground partners matters06:00 Scaling back travel advising and shifting priorities07:00 Living abroad in Uruguay with Boundless Life08:30 World schooling, community, and slow travel with kids09:30 Referral resources and Boundless Life episodes to revisit10:30 Choosing focus, presence, and family11:30 The decision to pause the podcast12:30 Why this pause is intentional, not an ending13:30 Encouragement to revisit past episodes14:30 Gratitude for the team behind the podcast15:30 Closing reflections and what comes nextResources & Links:Ready for your next adventure? Click here to view our Trip Planning Packages & 2025 Pricing: https://transform-with-travel.captivate.fm/packages Boundless Life Discount Code: KELTOL11Connect with meFollow the Podcast on IG: http://www.instagram.com/transformwithtravel Follow Kelly Tolliday on IG: http://www.instagram.com/kelly.tolliday Transform With Travel Website: https://www.transformwithtravel.co Email: kelly@travelkinship.com
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    11 mins
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