<![CDATA[Transform With Travel: Trip Planning Made Easy For Busy Professionals Craving Bucket List Adventures]]>e9f1eae1-d75b-52f2-ad0f-d3db999c9535Tue, 06 Jan 2026 11:00:41 +0000Captivate.fmKelly Tollidayhttps://artwork.captivate.fm/0b63dba1-81a2-4e9f-96a0-fec2dfb4c1f4/q01HXFYi9eLw5mLMMa3XYPEu.jpegTransform With Travel: Trip Planning Made Easy For Busy Professionals Craving Bucket List AdventuresKelly TollidayKelly TollidayAre 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.https://www.transformwithtravel.co/pages/podcastfalseepisodicnopodcast114: An Intentional Pause, A New Chapter, and Why Time Is the Ultimate Luxury114: An Intentional Pause, A New Chapter, and Why Time Is the Ultimate LuxuryWhat 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. 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: kelly@travelkinship.com

    ]]>    91bf0f1c-5ab6-4a31-8f77-f049a1eb6ba5Tue, 06 Jan 2026 06:00:00 -050011:02falsefull114114113: How to Experience Portugal Like a Local, Traditions, Villages, and Authentic Travel | Paula Alves113: How to Experience Portugal Like a Local, Traditions, Villages, and Authentic Travel | Paula AlvesWhat 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]]>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: kelly@travelkinship.com

      ]]>      40cbe970-68d2-4eda-a4fc-327286102f7dTue, 30 Dec 2025 06:00:00 -050030:46falsefull113113112: The Future of Adventure Travel, Luxury Trekking, National Parks, and Transformational Trips | Frank Castro112: The Future of Adventure Travel, Luxury Trekking, National Parks, and Transformational Trips | Frank CastroWhat 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:


      Connect with Adventure International