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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.
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117. The Harsh Reality of Living Overseas: Week 4 - 6 in Uruguay with Boundless Life
Episode 117
Thursday, May 21, 2026 • Duration 23:14
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.
In This Episode:
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
Follow the family’s Uruguay & worldschooling journey for more honest reflections on travel, parenting, surf life, and building community abroad :)
116. Life in Uruguay 🇺🇾 | Week 2 & 3 with Boundless Life + Honest Thoughts, Surprises & Tips
Episode 116
Wednesday, April 22, 2026 • Duration 17:09
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
115: Boundless Life in Uruguay: Week 1 in La Barra - Family Worldschool Adventure
Episode 115
Tuesday, April 14, 2026 • Duration 12:36
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:
💸 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💡 Tips If You're Considering This📅 What’s Coming Next💬 Let’s Connect
114: An Intentional Pause, A New Chapter, and Why Time Is the Ultimate Luxury
Episode 114
Tuesday, January 6, 2026 • Duration 11:02
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 content
How the podcast shaped her personal and professional growth over the last two and a half years
What a travel representation company does and why Travel Kinship felt like a natural next step
How ethical, sustainable, adventure-led travel has guided Kelly’s career decisions
Why her family chose to live abroad in Uruguay with Boundless Life
What global living offers children through education, community, and cultural immersion
Why time is the most valuable resource in intentional travel and intentional living
How to recognize when it’s time to pause something you love
Why stepping back does not mean stepping away forever
We talk about:
113: How to Experience Portugal Like a Local, Traditions, Villages, and Authentic Travel | Paula Alves
Episode 113
Tuesday, December 30, 2025 • Duration 30:46
What if your trip to Portugal went beyond the highlights and into the heart of everyday life?
In this episode of Transform With Travel, Kelly sits down with Paula Alves, co-founder of Portugal by TRAVELTAILORS, to explore what it truly means to experience Portugal through culture, tradition, and human connection.
Paula shares how her childhood spent between the United States and rural Portugal shaped her passion for preserving traditions, supporting small family-run businesses, and designing deeply personal itineraries that go far beyond Lisbon, Porto, and the Algarve. From village festivals and granite stone homes in the north to food, wine, crafts, and multi-generational storytelling, this conversation reveals why Portugal is best discovered slowly, thoughtfully, and with the right local partners.
This episode is an invitation to step off the checklist, reclaim time as the ultimate luxury, and experience Portugal as a living, breathing culture.
You will learn:
How Paula’s childhood in rural northern Portugal inspired the creation of Portugal by TRAVELTAILORS
Why Portuguese culture is rooted in tradition, community, and rural life
The difference between seeing Portugal’s cities and truly understanding the country
How gastronomy and wine experiences reveal the heart of Portuguese culture
Why small, family-owned businesses are central to sustainable travel
What makes private, intimate experiences more meaningful than mass tourism
Regions in Portugal advisors should emphasize beyond Lisbon and Porto
Why time, space, and immersion are the new luxury in travel
How Portugal is evolving as a destination for repeat visitors and premium travelers
We talk about:
00:00 Intro
02:30 Paula’s childhood between the U.S. and rural Portugal
112: The Future of Adventure Travel, Luxury Trekking, National Parks, and Transformational Trips | Frank Castro
Episode 112
Tuesday, December 23, 2025 • Duration 40:25
What if your next big adventure did more than give you a view, what if it gave you perspective?
In this episode, Kelly sits down with Frank Castro, founder of Adventure International, a luxury adventure outfitter known for high-end trekking and mountaineering experiences rooted in ethical guiding, fair wages, and deep respect for the local teams who make expeditions possible.
Frank shares how his early years operating in Tanzania sparked a mission to raise the standard for Kilimanjaro outfitting, not just through elevated logistics and top-tier gear, but through meaningful investment in guides, porters, cooks, training, and long-term community impact.
From there, Adventure International expanded into the Himalayas, Peru, and Ecuador, later growing into eco-dome glamping, conservation-driven safari camps, luxury surf travel, and privately guided U.S. National Parks experiences.
This conversation explores what makes a truly exceptional adventure DMC, why risk management is everything in high-altitude travel, and why more travelers are seeking experiences that reset the nervous system and reconnect them to what matters.
You will learn:
How Adventure International began as a high-level Kilimanjaro operator grounded in ethical labor practices
Why luxury adventure travel sits at the intersection of challenge and comfort
What travel advisors should look for in an adventure DMC, especially for high-risk itineraries
How Adventure International expanded from Tanzania into Nepal, Peru, and Ecuador
Why eco domes, glamping, and conservation-led travel are shaping the future
What families should consider when planning adventure travel across age ranges
Why nature-based travel is becoming essential in a screen-heavy world
How North America is emerging as a powerful adventure destination post-COVID
We talk about:
00:00 Intro
01:00 Travel Kinship, DMCs, and the role of ethical operators
111: The Best Travel Apps, Tools, and Resources for Intentional Trips in 2026 | Intentional Travel Series Ep 6
Episode 111
Tuesday, December 16, 2025 • Duration 16:26
What if planning your next trip felt calm, intentional, and fully supported instead of overwhelming and chaotic?
In the final episode of the Intentional Travel Series on Transform With Travel, Kelly shares her favorite travel apps, tools, companies, and resources that help create high ROI, stress free, deeply intentional trips in 2026 and beyond.
From flight research and airport transfers to hotel booking strategies, medical travel kits, insurance, group travel, retreats, financial tools, and vetted tour platforms, this episode is your complete intentional travel planning toolkit.
You will learn:
The difference between a travel advisor and travel coach and how to choose the right one
Why intentional travelers benefit from retreats and interest led group travel
How travel insurance protects both your finances and your nervous system
Why Kelly never travels without a Jetset Meds medical kit
How the US Smart Traveler Program adds a powerful layer of safety
The best apps for flights, hotels, airport transfers, and private stays
How to book hotels the smart way for better upgrades and perks
The pros and cons of major tour platforms versus local guides
The best itinerary builder for visual trip planning
How to manage international payments and group expenses stress free
Why the right tools turn good trips into transformational experiences
If you are traveling in 2026 and want your trip to feel aligned, safe, elevated, and easeful from planning to landing, this episode is your new travel companion.
📍 Watch the full Intentional Travel Planning Series for a step-by-step guide to creating trips that inspire growth, healing, and joy.
We talk about:
110: How to Integrate Your Travel Experience Into Your Real Life | Intentional Travel Series Ep 5
Episode 110
Tuesday, December 9, 2025 • Duration 12:22
Travel does not end when your plane lands, it actually begins when you return home. In this episode of the Intentional Travel Series on Transform With Travel, Kelly breaks down the missing piece most travelers never plan for, integration. How you turn what you felt, learned, and experienced on your trip into lasting habits, clarity, and life change.
Kelly walks you through a simple three phase integration framework including pre trip intention setting, mindful awareness during your travels, and post trip reflection that leads to real action. You will learn how to capture meaningful moments, identify what truly lit you up, and choose one small daily habit that keeps the energy of your trip alive long after you unpack your suitcase.
This episode also covers the emotional and logistical side of returning home, from reintegrating into work without overwhelm to avoiding the burnout that often follows even the most beautiful adventures. If you have ever come home from a trip inspired but unsure how to carry that inspiration forward, this episode will give you the tools to make your travel experiences truly transformational.
Inside this episode:
Why integration is the most overlooked part of intentional travel
How to set a powerful pre trip intention tied to your real life goals
The three journaling phases that make your trip more meaningful
How to capture daily moments of presence and nervous system regulation
What to reflect on before you return home so insights do not disappear
The formula for integration as intention plus action
Why choosing one small habit creates lasting change
How to avoid the post trip crash and reintegrate into work smoothly
Out of office strategies that protect your nervous system
How intentional travel creates sustainable lifestyle shifts
📍 Watch the full Intentional Travel Planning Series for a step-by-step guide to creating trips that inspire growth, healing, and joy.
We talk about:
109: Travel Without People Pleasing, How to Hold Boundaries on Any Trip | Intentional Travel Series Ep 4
Episode 109
Tuesday, December 2, 2025 • Duration 09:38
Intentional travel isn’t just about where you go or what you do, it’s also about how you protect your energy along the way.
In this episode of Transform With Travel, Kelly dives deep into the one thing most travelers forget to plan for boundaries. Whether you’re heading on a girls’ getaway, a multi-generational family trip, a solo retreat, or a wellness focused adventure, boundaries are the secret to making sure your trip actually supports your intention instead of derailing it.
From navigating group dynamics to avoiding resentment, from staying aligned with your wellness goals to practicing solo travel safety, Kelly breaks down practical, compassionate ways to communicate what you need and honor your intention without guilt.
Inside this episode:
How to set boundaries with friend groups, family, and travel partners
Why every group trip needs a clear leader and shared responsibilities
How to avoid resentment by defining what you will and won’t take on
The power of color coding activities for family travel fairness
Solo travel boundaries around safety, comfort, and confidence
How to practice solo travel at home to build your independence muscle
Wellness travel boundaries like alcohol free trips or digital detoxing
How to communicate your goals to your group so you feel supported
Why honoring your intention prevents burnout, people pleasing, and regret
If you’ve ever come home from a vacation feeling drained, frustrated, or like you never got what you needed from the trip, this episode will help you change that story for good.
📍 Watch the full Intentional Travel Planning Series for a step-by-step guide to creating trips that inspire growth, healing, and joy.
We talk about:
00:00 Welcome + What This Series Covers
01:00 Why Boundaries Matter in Intentional Travel
02:00 Group Travel Boundaries and Choosing Who Comes With You
108: How to Build a Balanced Travel Itinerary That Won’t Burn You Out | Intentional Travel Series Ep 3
Episode 108
Tuesday, November 25, 2025 • Duration 09:39
Your itinerary can make or break your trip, and today we’re rewriting the rules.
In this episode of Transform With Travel, Kelly guides you through how to build a balanced, aligned, and feels-good travel plan that supports your goals instead of draining your energy.
From creating a “loose plan” to building in yes days, rest days, and space for spontaneity, this episode helps you design an itinerary that elevates your whole trip. You’ll learn how to avoid overscheduling, reduce in-transit exhaustion, and plan activities that actually match your intention for your travels.
Whether you’re heading into a wellness reset, a family adventure, or a long-awaited dream destination, this episode gives you the framework to craft an itinerary that feels expansive, flexible, and deeply aligned with your season of life.
Inside this episode:
How to build a “loose plan” itinerary that leaves room for flow
Why one planned activity per day is the magic number
How to organize your trip around energy, not obligation
Why free days and “yes days” make trips more meaningful
The art of scheduling rest, rituals, and restorative moments
How to mix culture, nature, adventure, and downtime
Special tips for traveling with kids and avoiding travel burnout
How to make sure your itinerary reflects your deeper travel intention
If you’re ready to come home from your next trip relaxed and inspired instead of exhausted, this episode is your blueprint.
📍 Watch the full Intentional Travel Planning Series for a step-by-step guide to creating trips that inspire growth, healing, and joy.
We talk about:
00:00 Welcome + What This Series Covers
01:00 Why Balanced Itineraries Matter
02:00 The Magic of a Loose, Flexible Travel Plan
03:00 One Activity Per Day Rule
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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 💬
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
00:00 Intro
01:00 Reflecting on two and a half years of podcasting
02:00 Gratitude for listeners and the growth of the show
03:00 Announcing Kelly’s role at Travel Kinship
04:00 What travel representation companies do
05:00 Why working with on-the-ground partners matters
06:00 Scaling back travel advising and shifting priorities
07:00 Living abroad in Uruguay with Boundless Life
08:30 World schooling, community, and slow travel with kids
09:30 Referral resources and Boundless Life episodes to revisit
10:30 Choosing focus, presence, and family
11:30 The decision to pause the podcast
12:30 Why this pause is intentional, not an ending
