113: How to Experience Portugal Like a Local, Traditions, Villages, and Authentic Travel | Paula Alves

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

I’m back with another update from our family’s adventure in La Barra, Uruguay with Boundless Life 🌎 In this episode, I’m sharing what the past couple of weeks have really looked like—from settling into school and coworking life, to sneaking away for a wedding in Argentina, to the unexpected things that have surprised me (hello… mosquitoes 😅). If you’ve been curious about worldschooling, slow travel with kids, or what daily life actually feels like inside a Boundless Life program… this one’s for you. Thinking about Boundless Life for your family? Use my code KELTOL11 for a discount on your first program with Boundless Life ✨ IN THIS EPISODE: * What the welcome week experience looks like for families * Inside the school + coworking setup (and how it actually flows day-to-day) * Our quick trip to Mendoza for a wedding (with kids!) * How the kids adjusted to school + extracurriculars (surfing, art, cooking 🎨🌊) * What parent life looks like (coworking, community, social events) * The magic of being surrounded by 18 like-minded families from around the world * My honest take: is Boundless Life too good to be true? * Learning Spanish in Uruguay (and why it’s actually easier here) * The BIG surprise… the mosquito situation 🦟 * Practical tips: getting around, cost of living, and what to expect 🌊 REAL TALK HIGHLIGHTS: * This experience feels like life slowed down—in the best way * The community aspect has been one of the biggest unexpected wins * Uruguay is not a “cheap” destination—but it does feel safe, calm, and easy to live in * If you want to truly learn Spanish… this is the place 🚗 HELPFUL TIPS IF YOU’RE CONSIDERING LA BARRA: * A car or e-bike will make your life much easier * Expect cost of living similar to the U.S. (especially groceries + dining) * Take advantage of nearby gems like Portal Bosque and surrounding beach towns * Pack (a lot of) bug spray 💛 WHY WE’RE LOVING IT: There’s this rhythm here that just works—surf in the morning, work during the day, community and connection woven throughout. It feels full, aligned, and honestly… how life is meant to be lived. 🎁 THINKING ABOUT BOUNDLESS LIFE? Use my code KELTOL11 for a discount on your first program with Boundless Life 📩 LET’S CONNECT: Have questions about worldschooling, Uruguay, or Boundless Life? Drop them in the comments or reach out—I’m happy to share more 💬

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

Thinking about worldschooling with your family? Curious what life is actually like in Uruguay? This is your real, unfiltered Week 1 update from our 3-month adventure with Boundless Life in La Barra. I’m taking you behind the scenes of our experience—from the chaos of preparing to leave, to first impressions of this dreamy surf town, to what it actually feels like to land in a brand new country with kids, work, and zero routine. If you’ve been Googling, YouTubing, and trying to piece together what Boundless Life is really like (same 🙋‍♀️)… this series is for you. ✨ IN THIS EPISODE: * What Boundless Life is (think: study abroad… but for families) * Why we chose Uruguay over Europe, Bali, or Japan * Traveling from Florida → Montevideo → La Barra * The real prep process (spoiler: it’s a lot 😅) * Renting out our home + what we wish we knew * Traveling with dogs (and what we did instead 🐾) * First impressions of La Barra (Bali + Australia + California vibes 👀) * Our first week exploring: beaches, forests, surf, and nearby towns 📍 ABOUT BOUNDLESS LIFE Boundless Life is a global worldschooling program for families: * 🌍 8 locations around the world * 🏡 Fully set up homes or apartments * 🎓 Education center for kids (18 months–teens) * 💻 Co-working spaces for remote-working parents * 🤝 Built-in community of like-minded families 👉 Learn more: https://boundless.life [https://boundless.life] 💸 Use code KELTOL11 for €400 off your next program 🏄‍♀️ WHY WE CHOSE LA BARRA, URUGUAY * Closer to Eastern Time Zone for work * Spanish immersion for our family * Surf + beach lifestyle 🌊 * Slower, more peaceful destination 🌴 FIRST IMPRESSIONS La Barra feels like: * Bali (Canggu vibes) * Australia (Byron Bay / Bondi energy) * California coastlines All wrapped into one relaxed, beautiful, under-the-radar destination. 💡 TIPS IF YOU'RE CONSIDERING THIS * Start preparing your home WAY earlier than you think * Give yourself grace—the final month is intense * Arrive a few days (or a week!) early to settle in * Expect things to take longer than planned—and that’s okay 📅 WHAT’S COMING NEXT * First week of school with Boundless Life * Co-working space review * Daily routines + family rhythm * More local exploring 💬 LET’S CONNECT Have questions about Boundless Life or Uruguay? Drop them in the comments—I’m sharing everything I wish I knew before booking. 👍 If this helped you, like & subscribe for weekly updates from Uruguay! 💸 Ready to be Boundless? Use code KELTOL11 for €400 off your next program

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

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 [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 [http://www.instagram.com/transformwithtravel] 2. Follow Kelly Tolliday on IG: http://www.instagram.com/kelly.tolliday [http://www.instagram.com/kelly.tolliday] 3. Transform With Travel Website: https://www.transformwithtravel.co [https://www.transformwithtravel.co] 4. Email: kelly@travelkinship.com [kelly@travelkinship.com]

113: How to Experience Portugal Like a Local, Traditions, Villages, and Authentic Travel | Paula Alves

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 [https://transform-with-travel.captivate.fm/packages] Connect with Portugal by TRAVELTAILORS 1. Website: https://portugalbytraveltailors.com/ [https://portugalbytraveltailors.com/] Connect with me 1. Follow the Podcast on IG: http://www.instagram.com/transformwithtravel [http://www.instagram.com/transformwithtravel] 2. Follow Kelly Tolliday on IG: http://www.instagram.com/kelly.tolliday [http://www.instagram.com/kelly.tolliday] 3. Transform With Travel Website: https://www.transformwithtravel.co [https://www.transformwithtravel.co] 4. Email: kelly@travelkinship.com [kelly@travelkinship.com]

112: The Future of Adventure Travel, Luxury Trekking, National Parks, and Transformational Trips | Frank Castro

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 [https://transform-with-travel.captivate.fm/packages]  Connect with Adventure International * Facebook: https://www.facebook.com/100063483463682/info/# [https://www.facebook.com/100063483463682/info/#] * YouTube: https://www.youtube.com/AdventureIntnl [https://www.youtube.com/AdventureIntnl] * Instagram: https://www.instagram.com/adventureinternational/ [https://www.instagram.com/adventureinternational/] * Website: https://adventure-international.com/ [https://adventure-international.com/]  Connect with me * Follow the Podcast on IG: http://www.instagram.com/transformwithtravel [http://www.instagram.com/transformwithtravel]    * Follow Kelly Tolliday on IG: http://www.instagram.com/kelly.tolliday [http://www.instagram.com/kelly.tolliday]  * Transform With Travel Website: https://www.transformwithtravel.co [https://www.transformwithtravel.co]  * Email: kelly@travelkinship.com [kelly@travelkinship.com]