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

Kelly Tolliday
  • 4.9 (29)
  • PLACES & TRAVEL
  • UPDATED WEEKLY

Are you sitting behind your desk craving an adventure to make you feel alive again? But with thousands of travel options out there, where do you begin? Transform With Travel is designed for busy professionals who want more bucket lists trips that reignite adventure, go beneath the surface and feel unique to you WITHOUT the overwhelm of planning, the endless midnight scroll and the crowded tourist traps.

  1. APR 22

    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 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 💬

    17 min

  2. APR 14

    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 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 coastlines All 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

    13 min

  3. JAN 6

    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: 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 forever We 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 next Resources & 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: KELTOL11 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: kelly@travelkinship.com

    11 min

  4. 12/30/2025

    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: 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 travelers We 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 TRAVELTAILORS 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 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: kelly@travelkinship.com

    31 min

  5. 12/23/2025

    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 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-COVID We 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 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/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: kelly@travelkinship.com

    40 min

  6. 12/16/2025

    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 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 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 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 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

    16 min

  7. 12/09/2025

    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 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 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

    12 min

  8. 12/02/2025

    109: Travel Without People Pleasing, How to Hold Boundaries on Any Trip | Intentional Travel Series Ep 4

    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 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 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 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

    10 min
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4.9
out of 5
29 Ratings

About

Are you sitting behind your desk craving an adventure to make you feel alive again? But with thousands of travel options out there, where do you begin? Transform With Travel is designed for busy professionals who want more bucket lists trips that reignite adventure, go beneath the surface and feel unique to you WITHOUT the overwhelm of planning, the endless midnight scroll and the crowded tourist traps.

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