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

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]

111: The Best Travel Apps, Tools, and Resources for Intentional Trips in 2026 | Intentional Travel Series Ep 6

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 [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 [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]

110: How to Integrate Your Travel Experience Into Your Real Life | Intentional Travel Series Ep 5

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 [https://transform-with-travel.captivate.fm/packages]  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]  #TransformWithTravel #IntentionalTravel #TravelIntegration #PostTripGrowth #MindfulTravel #TravelTransformation #SustainableHabits #NervousSystemRegulation #WellnessTravel2026 #SlowTravelMovement #TravelWithPurpose #PersonalGrowthTravel