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

After three months living in Uruguay with Boundless Life from April - June, we wrapped up this chapter—but apparently not quite ready to leave. In fact, we loved it so much that we’ve decided to come back for another three months in September.

In this final episode of the Boundless Life series, I’m sharing a short and honest reflection on what these three months have meant for our family—the highs, the hard moments, and everything in between.

This experience wasn’t always easy. We navigated a death in the family, a major back injury, and plenty of the emotional ups and downs that come with living overseas with young kids. But somehow, Uruguay gave us exactly what we needed: a slower pace, a strong sense of community, more time together, and the space to actually experience life rather than constantly rushing through it.

We talk about what surprised us most about Uruguay, why we’ve fallen in love with this little corner of the world, our experience with Boundless Life’s education program, and why their new fully bilingual English/Spanish program in Uruguay is especially exciting for our family.

I also share what slow travel has taught us about how we want to travel and raise our kids—and why spending three to six months in one place feels so much better for our family than constantly moving from destination to destination.

And yes… we’re coming back. 🇺🇾

• Our honest final reflections after three months with Boundless Life
• The highs and lows of living overseas with young kids
• Why Uruguay completely surprised us
• The sense of safety, community, and belonging we found here
• How slow travel has changed the way we think about family travel
• Our experience with Boundless Life’s education program
• Why the new bilingual Spanish/English program in Uruguay is such a big deal for us
• The value of Spanish immersion and cultural immersion for our kids
• Why we decided to return to Uruguay for another three months
• What this experience has taught us about how we want to travel, live, and raise our family
• A big thank you to the Boundless Life team and teachers in Uruguay

If you’ve been following this Boundless Life series, thank you for coming along for the ride. And if you’re considering trying Boundless Life yourself, you can use code KELTOL11 for €400 off your program.

I receive referral credits for future Boundless Life programs when the code is used, but I am not paid directly.

This might be the end of this particular series—but definitely not the end of our Uruguay story.

🎧 Listen to the full Boundless Life series from the beginning for the complete behind-the-scenes experience.

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

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:

1. Why Kelly chose to start the year without vision boards or goal-setting content
2. How the podcast shaped her personal and professional growth over the last two and a half years
3. What a travel representation company does and why Travel Kinship felt like a natural next step
4. How ethical, sustainable, adventure-led travel has guided Kelly’s career decisions
5. Why her family chose to live abroad in Uruguay with Boundless Life
6. What global living offers children through education, community, and cultural immersion
7. Why time is the most valuable resource in intentional travel and intentional living
8. How to recognize when it’s time to pause something you love
9. Why stepping back does not mean stepping away forever

We talk about:

1. 00:00 Intro
2. 01:00 Reflecting on two and a half years of podcasting
3. 02:00 Gratitude for listeners and the growth of the show
4. 03:00 Announcing Kelly’s role at Travel Kinship
5. 04:00 What travel representation companies do
6. 05:00 Why working with on-the-ground partners matters
7. 06:00 Scaling back travel advising and shifting priorities
8. 07:00 Living abroad in Uruguay with Boundless Life
9. 08:30 World schooling, community, and slow travel with kids
10. 09:30 Referral resources and Boundless Life episodes to revisit
11. 10:30 Choosing focus, presence, and family
12. 11:30 The decision to pause the podcast
13. 12:30 Why this pause is intentional, not an ending
14. 13:30 Encouragement to revisit past episodes
15. 14:30 Gratitude for the team behind the podcast
16. 15:30 Closing reflections and what comes next

Resources & Links:

1. Ready for your next adventure? Click here to view our Trip Planning Packages & 2025 Pricing: https://transform-with-travel.captivate.fm/packages
2. Boundless Life Discount Code: KELTOL11

Connect with me

1. Follow the Podcast on IG: http://www.instagram.com/transformwithtravel
2. Follow Kelly Tolliday on IG: http://www.instagram.com/kelly.tolliday
3. Transform With Travel Website: https://www.transformwithtravel.co
4. Email: [email protected]

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:

1. How Paula’s childhood in rural northern Portugal inspired the creation of Portugal by TRAVELTAILORS
2. Why Portuguese culture is rooted in tradition, community, and rural life
3. The difference between seeing Portugal’s cities and truly understanding the country
4. How gastronomy and wine experiences reveal the heart of Portuguese culture
5. Why small, family-owned businesses are central to sustainable travel
6. What makes private, intimate experiences more meaningful than mass tourism
7. Regions in Portugal advisors should emphasize beyond Lisbon and Porto
8. Why time, space, and immersion are the new luxury in travel
9. How Portugal is evolving as a destination for repeat visitors and premium travelers

We talk about:

1. 00:00 Intro
2. 02:30 Paula’s childhood between the U.S. and rural Portugal
3. 04:00 Life in northern villages, family traditions, and simplicity
4. 06:00 The inspiration behind Portugal by TRAVELTAILORS
5. 07:30 Portuguese culture, tradition, and rural life vs modern cities
6. 09:30 Northern Portugal, villages, animals, landscapes, and architecture
7. 11:00 Gastronomy, cooking workshops, and wine-making experiences
8. 13:00 Harvest season, grape stomping, and authentic timing
9. 15:00 Working with artisans, chefs, and small producers
10. 17:00 Sustainability, relationships, and supporting family-owned businesses
11. 19:00 Intimacy vs mass tourism and why small experiences matter
12. 21:00 Regions advisors should promote beyond Lisbon & Porto
13. 23:00 Northern Portugal, national parks, forests, waterfalls, and villages
14. 25:00 Rethinking “touristy” and embracing cultural icons responsibly
15. 27:00 Luxury as time, space, and immersion
16. 29:00 Paula’s personal connection to northern Portugal
17. 31:00 Festivals, folklore, crafts, and living traditions
18. 33:00 The future of tourism in Portugal
19. 35:00 Islands, private stays, and immersive accommodations
20. 37:00 How advisors and travelers can connect with Portugal by TRAVELTAILORS

Resources & Links:

1. Ready for your next adventure? Click here to view our Trip Planning Packages & 2025 Pricing: https://transform-with-travel.captivate.fm/packages

Connect with Portugal by TRAVELTAILORS

1. Website: https://portugalbytraveltailors.com/

Connect with me

1. Follow the Podcast on IG: http://www.instagram.com/transformwithtravel
2. Follow Kelly Tolliday on IG: http://www.instagram.com/kelly.tolliday
3. Transform With Travel Website: https://www.transformwithtravel.co
4. Email: [email protected]

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
• 02:00 The origin story, Tanzania, Kilimanjaro, and “doing it the right way”
• 04:00 Ethical operations, wages, training, and industry shifts
• 06:00 Expanding into Nepal, Peru, and Ecuador
• 09:00 Eco domes, safari camps, and conservation impact
• 12:00 Luxury surf travel and concierge-style itineraries
• 13:30 COVID, U.S. National Parks, and family adventure travel
• 16:00 What makes a great adventure DMC and risk management realities
• 21:00 Setting expectations for iconic treks and crowd realities
• 23:00 Building balanced itineraries with elevated extensions
• 25:00 Why adventure travel is rising as nervous system medicine
• 28:00 Transformational moments and shared humanity on the trail
• 32:00 Family travel guidance and age considerations
• 35:00 Slowing down, North America focus, and full-circle travel
• 39:00 Closing reflections and next steps

Resources & Links:

• Ready for your next adventure? Click here to view our Trip Planning Packages & 2025 Pricing: https://transform-with-travel.captivate.fm/packages 

Connect with Adventure International

• Facebook: https://www.facebook.com/100063483463682/info/#
• YouTube: https://www.youtube.com/AdventureIntnl
• Instagram: 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] 

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:

• 00:00 Welcome + What This Series Covers  
• 01:00 Why tools and resources matter for intentional travel
• 02:00 Travel advisors vs travel coaches and sabbatical support
• 04:00 Solo travel, retreats, and interest led group trips
• 06:00 Travel insurance and medical safety while abroad
• 07:00 Jetset Meds, the travel medical kit Kelly never leaves without
• 08:00 The Smart Traveler Program and emergency protection
• 09:00 Best apps for flights and transfers
• 10:00 How to research and book hotels the right way
• 11:30 Private homes and vetted luxury stays
• 12:30 Tours, excursions, and booking local guides
• 13:30 Digital itinerary builders for seamless travel
• 14:15 International payments and group expense tracking
• 15:00 Final reflections and how to plan your next intentional trip

Resources & 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 kit

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 

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:

• 00:00 Welcome + What This Series Covers  
• 01:00 What integration really means in travel
• 02:00 Using trips to support larger life goals
• 03:00 Pre trip intention setting and visualization
• 04:00 How to track meaningful moments during your trip
• 06:00 Post trip reflection and identifying what lit you up
• 07:30 The integration formula, intention plus action
• 08:40 Choosing one daily habit that actually sticks
• 09:50 Returning home without chaos and burnout
• 11:00 Out of office strategies and gentle work reintegration
• 12:00 What is coming next on Transform With Travel

Resources & Links:

• Ready for your next adventure? Click here to view our Trip Planning Packages & 2025 Pricing: https://transform-with-travel.captivate.fm/packages 

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 

#TransformWithTravel #IntentionalTravel #TravelIntegration #PostTripGrowth #MindfulTravel #TravelTransformation #SustainableHabits #NervousSystemRegulation #WellnessTravel2026 #SlowTravelMovement #TravelWithPurpose #PersonalGrowthTravel

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
• 03:00 How to Share Planning Responsibilities Without Resentment
• 04:00 Expense Splitting, Chores, and Group Harmony
• 05:00 Multi Generational Travel and Color Coding Activities
• 06:00 Solo Travel Boundaries, Safety, and Building Confidence
• 07:00 Practicing Solo Travel Before Your Trip
• 07:40 Boutique Hotels, Retreats, and Supportive Solo Options
• 08:00 Wellness Travel Boundaries, Alcohol Free Trips, and Digital Detoxes
• 09:00 Letting Your Group In on Your Goals so They Can Support You
• 09:40 What’s Coming Next in the Intentional Travel Series

Resources & Links:

• Ready for your next adventure? Click here to view our Trip Planning Packages & 2025 Pricing: https://transform-with-travel.captivate.fm/packages 

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