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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 lossMultiple surfing and back injuries Why having a built-in village through Boundless Life changed everythingThe unexpected transformation that happens when you allow new people into your life overseasThis 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 programThe emotional reality of leaving a strong support system at homeBuilding deep friendships quickly while living abroadThe “week 4 slump” many families experience during long-term travelHow the Boundless Life community became a true support networkWhy village and community matter more than locationReflections on parenting, identity, and personal growth overseasSurfing injuries, SI joint rehab, and navigating healthcare abroadMid-cohort travel to Punta del Diablo & Santa Teresa National ParkThe beauty and difficulty of creating a life outside your comfort zone
Mentioned in This Episode:Boundless LifeLa Barra, UruguayWorkschoolingEpisode #55: Parenting Across Cultures with Elodie Fourchaud
Boundless Life Discount Code :)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.)
Connect & Follow Along :)Podcast: Transform With TravelInstagram: @kelly.tollidayFollow the family’s Uruguay & worldschooling journey for more honest reflections on travel, parenting, surf life, and building community abroad :)
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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 familiesInside 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 worldMy 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 wayThe community aspect has been one of the biggest unexpected winsUruguay is not a “cheap” destination—but it does feel safe, calm, and easy to live inIf 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 easierExpect cost of living similar to the U.S. (especially groceries + dining)Take advantage of nearby gems like Portal Bosque and surrounding beach townsPack (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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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 JapanTraveling from Florida → Montevideo → La BarraThe real prep process (spoiler: it’s a lot 😅)Renting out our home + what we wish we knewTraveling 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 LifeBoundless 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, UruguayCloser to Eastern Time Zone for workSpanish immersion for our familySurf + beach lifestyle 🌊Slower, more peaceful destination
🌴 First ImpressionsLa Barra feels like:
Bali (Canggu vibes)Australia (Byron Bay / Bondi energy)California coastlinesAll wrapped into one relaxed, beautiful, under-the-radar destination.
💡 Tips If You're Considering ThisStart preparing your home WAY earlier than you thinkGive yourself grace—the final month is intenseArrive a few days (or a week!) early to settle inExpect things to take longer than planned—and that’s okay
📅 What’s Coming NextFirst week of school with Boundless LifeCo-working space reviewDaily routines + family rhythmMore local exploring
💬 Let’s ConnectHave 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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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 me
Follow 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: [email protected]
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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 TRAVELTAILORSWhy Portuguese culture is rooted in tradition, community, and rural lifeThe difference between seeing Portugal’s cities and truly understanding the countryHow gastronomy and wine experiences reveal the heart of Portuguese cultureWhy small, family-owned businesses are central to sustainable travelWhat makes private, intimate experiences more meaningful than mass tourismRegions in Portugal advisors should emphasize beyond Lisbon and PortoWhy time, space, and immersion are the new luxury in travelHow Portugal is evolving as a destination for repeat visitors and premium travelersWe talk about:
00:00 Intro 02:30 Paula’s childhood between the U.S. and rural Portugal04:00 Life in northern villages, family traditions, and simplicity06:00 The inspiration behind Portugal by TRAVELTAILORS07:30 Portuguese culture, tradition, and rural life vs modern cities09:30 Northern Portugal, villages, animals, landscapes, and architecture11:00 Gastronomy, cooking workshops, and wine-making experiences13:00 Harvest season, grape stomping, and authentic timing15:00 Working with artisans, chefs, and small producers17:00 Sustainability, relationships, and supporting family-owned businesses19:00 Intimacy vs mass tourism and why small experiences matter21:00 Regions advisors should promote beyond Lisbon & Porto23:00 Northern Portugal, national parks, forests, waterfalls, and villages25:00 Rethinking “touristy” and embracing cultural icons responsibly27:00 Luxury as time, space, and immersion29:00 Paula’s personal connection to northern Portugal31:00 Festivals, folklore, crafts, and living traditions33:00 The future of tourism in Portugal35:00 Islands, private stays, and immersive accommodations37:00 How advisors and travelers can connect with Portugal by TRAVELTAILORSResources & Links:
Ready for your next adventure? Click here to view our Trip Planning Packages & 2025 Pricing: https://transform-with-travel.captivate.fm/packagesConnect with Portugal by TRAVELTAILORS
Website: https://portugalbytraveltailors.com/Connect with me
Follow 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: [email protected]
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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 practicesWhy luxury adventure travel sits at the intersection of challenge and comfortWhat travel advisors should look for in an adventure DMC, especially for high-risk itinerariesHow Adventure International expanded from Tanzania into Nepal, Peru, and EcuadorWhy eco domes, glamping, and conservation-led travel are shaping the futureWhat families should consider when planning adventure travel across age rangesWhy nature-based travel is becoming essential in a screen-heavy worldHow North America is emerging as a powerful adventure destination post-COVIDWe talk about:
00:00 Intro 01:00 Travel Kinship, DMCs, and the role of ethical operators02:00 The origin story, Tanzania, Kilimanjaro, and “doing it the right way”04:00 Ethical operations, wages, training, and industry shifts06:00 Expanding into Nepal, Peru, and Ecuador09:00 Eco domes, safari camps, and conservation impact12:00 Luxury surf travel and concierge-style itineraries13:30 COVID, U.S. National Parks, and family adventure travel16:00 What makes a great adventure DMC and risk management realities21:00 Setting expectations for iconic treks and crowd realities23:00 Building balanced itineraries with elevated extensions25:00 Why adventure travel is rising as nervous system medicine28:00 Transformational moments and shared humanity on the trail32:00 Family travel guidance and age considerations35:00 Slowing down, North America focus, and full-circle travel39:00 Closing reflections and next stepsResources & Links:
Ready for your next adventure? Click here to view our Trip Planning Packages & 2025 Pricing: https://transform-with-travel.captivate.fm/packagesConnect with Adventure International
Facebook: https://www.facebook.com/100063483463682/info/#YouTube: https://www.youtube.com/AdventureIntnlInstagram: https://www.instagram.com/adventureinternational/Website: https://adventure-international.com/Connect with me
Follow 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: [email protected]
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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 oneWhy intentional travelers benefit from retreats and interest led group travelHow travel insurance protects both your finances and your nervous systemWhy Kelly never travels without a Jetset Meds medical kitHow the US Smart Traveler Program adds a powerful layer of safetyThe best apps for flights, hotels, airport transfers, and private staysHow to book hotels the smart way for better upgrades and perksThe pros and cons of major tour platforms versus local guidesThe best itinerary builder for visual trip planningHow to manage international payments and group expenses stress freeWhy the right tools turn good trips into transformational experiencesIf 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:
00:00 Welcome + What This Series Covers 01:00 Why tools and resources matter for intentional travel02:00 Travel advisors vs travel coaches and sabbatical support04:00 Solo travel, retreats, and interest led group trips06:00 Travel insurance and medical safety while abroad07:00 Jetset Meds, the travel medical kit Kelly never leaves without08:00 The Smart Traveler Program and emergency protection09:00 Best apps for flights and transfers10:00 How to research and book hotels the right way11:30 Private homes and vetted luxury stays12:30 Tours, excursions, and booking local guides13:30 Digital itinerary builders for seamless travel14:15 International payments and group expense tracking15:00 Final reflections and how to plan your next intentional tripResources & Links:
Ready for your next adventure? Click here to view our Trip Planning Packages & 2025 Pricing: https://transform-with-travel.captivate.fm/packages Jetset Meds Discount Code: Use code TRANSFORM10 for 10% off your first kitConnect with me
Follow 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
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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 travelHow to set a powerful pre trip intention tied to your real life goalsThe three journaling phases that make your trip more meaningfulHow to capture daily moments of presence and nervous system regulationWhat to reflect on before you return home so insights do not disappearThe formula for integration as intention plus actionWhy choosing one small habit creates lasting changeHow to avoid the post trip crash and reintegrate into work smoothlyOut of office strategies that protect your nervous systemHow 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:
00:00 Welcome + What This Series Covers 01:00 What integration really means in travel02:00 Using trips to support larger life goals03:00 Pre trip intention setting and visualization04:00 How to track meaningful moments during your trip06:00 Post trip reflection and identifying what lit you up07:30 The integration formula, intention plus action08:40 Choosing one daily habit that actually sticks09:50 Returning home without chaos and burnout11:00 Out of office strategies and gentle work reintegration12:00 What is coming next on Transform With TravelResources & Links:
Ready for your next adventure? Click here to view our Trip Planning Packages & 2025 Pricing: https://transform-with-travel.captivate.fm/packagesConnect with me
Follow 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#TransformWithTravel #IntentionalTravel #TravelIntegration #PostTripGrowth #MindfulTravel #TravelTransformation #SustainableHabits #NervousSystemRegulation #WellnessTravel2026 #SlowTravelMovement #TravelWithPurpose #PersonalGrowthTravel
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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 partnersWhy every group trip needs a clear leader and shared responsibilitiesHow to avoid resentment by defining what you will and won’t take onThe power of color coding activities for family travel fairnessSolo travel boundaries around safety, comfort, and confidenceHow to practice solo travel at home to build your independence muscleWellness travel boundaries like alcohol free trips or digital detoxingHow to communicate your goals to your group so you feel supportedWhy honoring your intention prevents burnout, people pleasing, and regretIf 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 Travel02:00 Group Travel Boundaries and Choosing Who Comes With You03:00 How to Share Planning Responsibilities Without Resentment04:00 Expense Splitting, Chores, and Group Harmony05:00 Multi Generational Travel and Color Coding Activities06:00 Solo Travel Boundaries, Safety, and Building Confidence07:00 Practicing Solo Travel Before Your Trip07:40 Boutique Hotels, Retreats, and Supportive Solo Options08:00 Wellness Travel Boundaries, Alcohol Free Trips, and Digital Detoxes09:00 Letting Your Group In on Your Goals so They Can Support You09:40 What’s Coming Next in the Intentional Travel SeriesResources & Links:
Ready for your next adventure? Click here to view our Trip Planning Packages & 2025 Pricing: https://transform-with-travel.captivate.fm/packagesConnect with me
Follow 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
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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 flowWhy one planned activity per day is the magic numberHow to organize your trip around energy, not obligationWhy free days and “yes days” make trips more meaningfulThe art of scheduling rest, rituals, and restorative momentsHow to mix culture, nature, adventure, and downtimeSpecial tips for traveling with kids and avoiding travel burnoutHow to make sure your itinerary reflects your deeper travel intentionIf 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 Matter02:00 The Magic of a Loose, Flexible Travel Plan03:00 One Activity Per Day Rule04:00 Why Overscheduling Leads to Stress and Burnout05:00 Adding Free Days and Yes Days05:40 Local Recommendations, Hidden Gems, and Spontaneity06:00 Scheduling Rest, Rituals, and Recharging07:00 Balancing Culture, Nature, Adventure, and Relaxation07:50 Traveling With Kids, Energy Management, and Expectations08:20 Aligning Itinerary Choices With Your Big Travel Intention09:00 What’s Coming Next in the Intentional Travel SeriesResources & Links:
Ready for your next adventure? Click here to view our Trip Planning Packages & 2025 Pricing: https://transform-with-travel.captivate.fm/packagesConnect with me
Follow 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
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Where you go matters, but why you go matters even more.
In this episode of Transform With Travel, we dive into the art of destination selection – helping you choose where to travel based on your goals, values, and energy. Whether you’re planning a health reset, a romantic getaway, or a creative sabbatical, Kelly shows you how to pick a destination that truly supports your intention.
From Greece’s healing blue zones to the quiet beauty of Costa Rica’s jungles, this episode explores how to bring more meaning to your adventures and make every trip feel like it was designed just for you.
Inside this episode:
How to align your destination with your travel intentionThe difference between “destination-first” vs. “intention-first” travelHow your budget shapes where (and how) you travelThe truth about “Instagram vs. Reality” tourismWhen to travel for best experiences (low, shoulder, or high season)How to avoid travel stress and find destinations that match your season of lifeIf you’re ready to make your 2026 travels intentional, transformational, and totally aligned with you, this episode is your roadmap.
📍 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 01:10 Why Destination Choice Matters 02:00 How to Pick Health, Wellness, or Connection Destinations 04:00 Budget, Season, and Reality Checks 06:00 Avoiding Overtourism and Stress 07:10 Timing, Seasons, and Restrictions 08:00 How to Align Your Destination With Your Goals 08:30 What’s Next: Building a Balanced ItineraryResources & Links:
Ready for your next adventure? Click here to view our Trip Planning Packages & 2025 Pricing: https://transform-with-travel.captivate.fm/packagesConnect with me
Follow 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
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What if your next trip could change your life, not just your location?
In this episode of Transform With Travel, we kick off the Intentional Travel Planning Series, where I share how to plan bucket-list trips that align with your goals, values, and season of life.
Discover how to plan your 2026 adventures with purpose, whether it’s a healing solo trip to Greece, a yoga retreat in the islands, or a digital detox in Sweden. I guide you through how to set travel intentions, choose destinations that match your energy, and make every journey an act of self-discovery.
Inside this episode:
How to align your travel plans with your personal goals and valuesTurning bucket-list trips into meaningful, mindful experiencesWhy intentional travel doesn’t mean boring travelReal stories of transformation through travelHow to start planning your 2026 adventures now, stress-freeIf you’re craving adventure that feels good for your soul and your schedule, this series is for you.
📍 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 to Transform With Travel | What Is Intentional Travel 01:30 Intentional Travel Isn’t Boring | A Healing Trip to Greece 03:30 Align Your Life Goals With Travel Goals 05:00 Travel for Health, Growth, and Relationships 07:00 Purposeful Career Travel and Sabbatical Inspiration 08:00 Hobby-Based and Joyful Travel Ideas 09:20 Practical Steps to Plan Your Trip With Intention 10:15 What’s Coming Next | The Perfect Destination for YouResources & Links:
Ready for your next adventure? Click here to view our Trip Planning Packages & 2025 Pricing: https://transform-with-travel.captivate.fm/packagesConnect with me
Follow 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
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Are you ready to transform your travel experiences and maybe even your career through the world of travel?
In this episode of the Transform with Travel podcast, I sit down with Henley Vasquez, the CEO and co-founder of Fora. This conversation illuminated the evolving landscape of the travel industry, the rise of travel advisors, and the growing interest in wellness travel.
We got into the changes in the travel industry, particularly post-pandemic. The demand for travel advisors has surged as travelers seek guidance through the more complex travel landscape. The conversation highlighted the growing need for flexibility and the ability for last-minute planning, as people are still wary of committing to travel plans far in advance.
Fora aims to revolutionize the travel advising industry by offering a modern platform that supports advisors with training, efficient booking tools, and community connection. This approach not only helps seasoned advisors but also makes it easier for newcomers to enter the field and succeed.
Henley shared some exciting travel trends, including a move towards exploring less touristy areas in popular destinations like Italy and the rise of far-flung destinations such as Bhutan. She also noted the continued popularity of domestic travel within the United States, with destinations like the American West offering unique experiences.
We talk about:
00:00 Intro04:56 The Evolution of the Travel Industry09:17 Introducing Fora: A Modern Travel Agency16:25 The Power of Community in Travel Advising20:12 Becoming a Standout Travel Advisor22:41 The Power of Word of Mouth in Travel24:02 The Rise of Wellness Travel28:05 Emerging Travel Trends and Destinations33:17 The Value of Local and Simple Travel42:16 Final Thoughts and Becoming a Travel AdvisorResources & Links:
Ready for your next adventure? Click here to view our Trip Planning Packages & 2025 Pricing: https://transform-with-travel.captivate.fm/packagesConnect with Henley
https://www.foratravel.com/ https://www.instagram.com/hellofora/ https://www.instagram.com/henleyv/Connect with me
Follow 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
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Travel holds an unparalleled ability to transform lives. It’s not just about the destinations visited but the personal growth and self-discovery that happen along the way. In this episode of Transform with Travel, I sit down with Gabriella Arbesu, a long-time friend and avid traveler, about the profound impacts of her travel journey.
Gabi shares the influence of her Cuban-American heritage on her identity, painting a vivid picture of growing up in a bustling and loud Cuban household against the backdrop of a quieter American culture. This duality of cultures shaped her into a bold, unapologetic individual, proud of her heritage and open to the world’s diversity.
This episode is a testament to the power of travel and personal growth. It’s a reminder that we all have the power to transform our lives through our journeys, both literal and metaphorical. I encourage you to embrace the unknown, pursue your passions, and let the world open your minds and hearts to new perspectives.
Share your thoughts: How has travel transformed you? Join the conversation and let us know your story of transformation through travel!
We talk about:
00:00 Intro01:47 Exploring Cuban-American Heritage and Growing Up in South Florida05:09 Gabby's Yoga Journey: From Trauma to Transformation09:27 The Art of Holding Space: Lessons from Yoga and Retreats09:53 The Impact of Travel on Personal Growth and Cultural Connection29:14 Navigating Relationships and Travel: Moving to Central America29:51 The Reality of Living Abroad: Challenges and Triumphs35:21 Falling in Love with Nicaragua36:13 The Decision to Buy Land36:59 Understanding Property Ownership in Nicaragua37:42 Building a Dream: From Vision to Reality39:41 Exploring the Future of Yoga Retreats41:57 Embracing Creativity: The OnlyFans JourneyResources & Links:
Ready for your next adventure? Click here to view our Trip Planning Packages & 2025 Pricing: https://transform-with-travel.captivate.fm/packagesConnect with Gabi
Instagram: https://www.instagram.com/gabriella__cristinahttps://hoo.be/gabriellacristinaConnect with me
Follow 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
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Are you yearning for an experience that could transform not just your family’s outlook on the world, but also improve your own as a parent?
Are you curious about how different cultures parent their children?
In today’s fast-paced, technology-driven world, the notion of slow travel can create the perfect environment for personal growth and connection. Join Elodie Ferchaud, co-founder of Boundless Life, and I as we navigate the world of travel for families.
Elodie’s journey started out as an expat family, where she observed the differences in parenting across cultures - Swedish, French, Japanese and American. Because of this cross-cultural experience, she was able to blend the best of all 4 parenting styles into her own version of mothering.
Boundless Life stands out with its thoughtfully crafted communities in places like Greece, Portugal, and Bali, aiming to provide holistic family living solutions. These include schooling based on experiential learning and tight-knit support networks for parents and children alike.
Boundless Life’s approach to education is innovative, emphasizing growth mindset and holistic child development through modular, multi-age learning environments. Kids not only partake in culturally immersive activities but also benefit from stable, supportive learning surroundings that mitigate the transitions typically associated with frequent relocations.
We talk about:
00:00 Intro03:08 Parenting Across Cultures08:23 Elodie's Expat Life Before Boundless Life24:39 Living the Boundless Life: Experiences in Portugal, Greece, and Bali28:00 The Impact of Travel on Parenting and Personal Growth32:21 Boundless Life Program Details and Flexibility33:44 Traveling with Familiar Faces34:13 Creating a Consistent Learning Environment35:21 The Benefits of Multi-Age Learning37:53 Growth Mindset in Education38:50 Parental Growth Through Travel45:11 The Power of Community in Parenting50:13 Joining Boundless Life53:52 Future Plans for Boundless LifeResources & Links:
Ready for your next adventure? Click here to view our Trip Planning Packages & 2025 Pricing: https://transform-with-travel.captivate.fm/packages Bringing Up Bébé: https://a.co/d/hz9QYTB There’s No Such Thing As Bad Weather: https://a.co/d/9sp4ZI2 French Children Don’t Throw Food: https://a.co/d/10wtCy7Connect with Elodie
Instagram: www.instagram.com/boundlesslife https://www.boundless.life/Connect with me
Follow 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
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Are you ready to transform your travel experiences into moments of depth and personal growth? In today's fast-paced world, travel has become more than just checking destinations off a list. It's about immersing yourself in new cultures, embracing challenges, and living with intention. This concept of intentional travel was the highlight of our recent conversation with Kelly Fischer.
Traveling often promises the allure of adventure and the temptation of Instagram-worthy spots. Yet, as Kelly shares, it's about the deeper experiences found beyond the crowded tourist traps and social media snapshots. These are the moments where you find yourself truly present, whether you're savoring a buttery croissant in France or navigating an unknown village in northern Italy.
Kelly's adventures highlight how stepping into the unknown isn't just about seeing new places; it's about personal growth. Surrounded by the unfamiliar, she found a deeper trust in herself and an ability to embrace the unexpected twists of travel. Her story reminds us that even the journey itself, with all its challenges and surprises, is just as rewarding as the destination.
We talk about:
00:00 Intro03:25 Building Conscious Brands05:58 Living with Depth and Presence12:39 Kelly's Journey to Italy15:38 Embracing Uncomfortable Growth19:40 The Value of Intentional Travel24:22 Advice on Taking Leaps of Faith26:36 The Power of Curiosity and Learning28:33 Living in the Present Moment32:03 Maintaining Wellness Routines While Traveling34:50 The Concept of Pocketing Experiences41:24 Rapid Fire Travel QuestionsResources & Links:
Ready for your next adventure? Click here to view our Trip Planning Packages & 2025 Pricing: https://transform-with-travel.captivate.fm/packagesConnect with Kelly Fischer:
Website: www.depththeory.com Instagram: www.instagram.com/depththeoryConnect with Kelly
Follow 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
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Are you willing to step into the unknown to bring your dreams to life? In this episode of the Transform with Travel podcast, I had an enlightening conversation with Marisa Folz McConnell, a visionary entrepreneur behind The Wander Shop.
The Wander Shop was born out of Marisa's love for travel and fashion. Initially envisioned as a mobile store, Marisa's ingenuity and grit saw it evolve into a lifestyle boutique that supports local brands and artisans. With every change in her business model, from pop-up events and roaming Airstreams to stable retail locations, Marisa demonstrates the importance of flexibility and intuition in entrepreneurial success.
Travel has been a major influence on Marisa's fashion sense and business ethos. She draws inspiration from California’s laid-back style and Italy's classic elegance, incorporating versatile, timeless fashion pieces in her store. Trend forecasting for 2025 sees the return of baggy jeans and bold colors, and Marisa advises building a capsule wardrobe that balances the trendy with the timeless.
Marisa's story is a reminder to trust your instincts and seize opportunities when they arise. Her willingness to embrace risks and adapt to new circumstances offers a valuable lesson for anyone looking to transform their vision into reality.
We talk about:
00:00 Intro04:50 The Origin of The Wander Shop08:14 Challenges and Evolutions09:43 Embracing Change and Growth11:17 Balancing Routine and Spontaneity23:10 Travel Influences and Style25:56 Packing Tips for Overpackers28:16 Photo Tips and Background Remover28:33 Packing Strategies and Outfit Planning29:33 Content Creation and Brand Building30:20 Revisiting Favorite Travel Destinations38:38 Planning the Perfect Girls Trip43:40 Fashion Trends for 202546:08 Running a Small BusinessResources & Links:
Ready for your next adventure? Click here to view our Trip Planning Packages & 2025 Pricing: https://transform-with-travel.captivate.fm/packagesConnect with Marisa
Instagram: https://www.instagram.com/tothewandershop TikTok: https://www.tiktok.com/@tothewandershop https://thewandershop.com/Connect with Kelly
Follow 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
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In this milestone 100th episode of Transform With Travel, we highlight the transformative power of travel in shaping lives, relationships, and legacies while acknowledging the resurgence of travel post-pandemic and its associated challenges like overtourism and stressed ecosystems.
We talk about the role of travel advisors in promoting sustainable and responsible travel choices, aiming to shift from being mere consumers to stewards of travel. As we look forward to the future, I hope for more intentional, community-supportive, and culturally preservative travel.
Thanks for tuning in and celebrating 100 episodes, here’s to the next 100!
We talk about:
00:00 Intro01:11 The State of Global Travel Post-Pandemic01:30 The Impact of Overtourism02:28 Responsible Travel Choices03:22 The Role of Travel Advisors04:35 Future of Travel and Podcast Vision05:38 Final Thoughts and Next StepsResources & Links:
Ready for your next adventure? Click here to view our Trip Planning Packages & 2025 Pricing: https://transform-with-travel.captivate.fm/packagesConnect with Kelly
Follow 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
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Have you ever wondered what it's like to view the world from the cockpit of an airplane? Or perhaps you're one of the many travelers who experience a tinge of anxiety every time you buckle up for a flight. In today's episode, we unravel these mysteries with insights from a seasoned pilot, Simon Brackett, and learn practical ways to manage in-flight anxiety.
Travel can open up new perspectives and enhance the quality of our lives. Traveling can be transformational, however, for many, stepping on an airplane introduces a wave of nervousness, often due to turbulence or unfamiliar sounds during a flight. Understanding the process and realities of flying can ease anxiety, allowing one to fully embrace the adventurous spirit that travel promises.
One of the most common fears associated with flying is turbulence. Simon Brackett, a commercial pilot and former Air Force special operations pilot, clarifies that turbulence doesn't mean danger. He compares it to a boat riding over choppy water — uncomfortable but manageable. Simon reassures us that he's never encountered structural damage to an aircraft due to turbulence. He also shares his best tips for staying safe, as well as for managing flight anxiety.
Understanding the mechanics and safety of flying, coupled with mindful practices, can vastly improve your travel experience. Embrace these tips and insights next time you embark on your journey, and remember to keep exploring the horizons, grounded in the confidence of a safe flight.
We talk about:
00:00 Intro00:50 Coping with Flight Anxiety05:36 Understanding Flight Safety11:25 Simon Brackett's Aviation Journey18:43 The Reality of Turbulence25:31 Seatbelt Safety Explained33:44 Overcoming Claustrophobia on Flights34:53 Understanding Flight Delays39:21 Pilot Communication Styles42:38 Traveling with Young Children45:49 Addressing Passenger Concerns50:07 The Joys of Being a Pilot54:20 Travel Tips and Life Lessons01:05:41 Conclusion and Next StepsIn this episode:
Episode 43: https://transform-with-travel.captivate.fm/episode/043-how-yoga-and-meditation-can-help-you-become-a-better-traveler-with-justin-liebmanResources & Links:
Ready for your next adventure? Click here to view our Trip Planning Packages & 2025 Pricing: https://transform-with-travel.captivate.fm/packagesConnect with Kelly
Follow 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
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In this episode, I share the extraordinary journey of how I met my husband Sam.
The story spans continents and years, beginning with my decision to study abroad in Switzerland and culminating in a chance encounter at a pub crawl in Dublin.
As we relationship, we faced long-distance challenges and numerous adventures, ultimately leading me to move to Australia. Now, nearly a decade later, we are married with two children, and continue to infuse our lives with travel and exploration. Our story emphasizes the power of saying 'yes' to life’s adventures and how one decision can change everything.
We talk about:
00:00 Intro02:00 The Switzerland Study Abroad Experience03:20 The Ireland Adventure Begins07:15 Meeting Sam in Dublin16:26 A New Year's Reunion in Europe21:47 Building a Life Together29:33 Final ThoughtsResources & Links:
Ready for your next adventure? Click here to view our Trip Planning Packages & 2025 Pricing: https://transform-with-travel.captivate.fm/packagesConnect with Kelly
Follow 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
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