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

Your itinerary can make or break your trip, and today we’re rewriting the rules.

In this episode of Transform With Travel, Kelly guides you through how to build a balanced, aligned, and feels-good travel plan that supports your goals instead of draining your energy.

From creating a “loose plan” to building in yes days, rest days, and space for spontaneity, this episode helps you design an itinerary that elevates your whole trip. You’ll learn how to avoid overscheduling, reduce in-transit exhaustion, and plan activities that actually match your intention for your travels.

Whether you’re heading into a wellness reset, a family adventure, or a long-awaited dream destination, this episode gives you the framework to craft an itinerary that feels expansive, flexible, and deeply aligned with your season of life.

Inside this episode:

• How to build a “loose plan” itinerary that leaves room for flow
• Why one planned activity per day is the magic number
• How to organize your trip around energy, not obligation
• Why free days and “yes days” make trips more meaningful
• The art of scheduling rest, rituals, and restorative moments
• How to mix culture, nature, adventure, and downtime
• Special tips for traveling with kids and avoiding travel burnout
• How to make sure your itinerary reflects your deeper travel intention

If you’re ready to come home from your next trip relaxed and inspired instead of exhausted, this episode is your blueprint.

📍 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 Balanced Itineraries Matter
• 02:00 The Magic of a Loose, Flexible Travel Plan
• 03:00 One Activity Per Day Rule
• 04:00 Why Overscheduling Leads to Stress and Burnout
• 05:00 Adding Free Days and Yes Days
• 05:40 Local Recommendations, Hidden Gems, and Spontaneity
• 06:00 Scheduling Rest, Rituals, and Recharging
• 07:00 Balancing Culture, Nature, Adventure, and Relaxation
• 07:50 Traveling With Kids, Energy Management, and Expectations
• 08:20 Aligning Itinerary Choices With Your Big Travel Intention
• 09:00 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 

Where you go matters, but why you go matters even more.

In this episode of Transform With Travel, we dive into the art of destination selection – helping you choose where to travel based on your goals, values, and energy. Whether you’re planning a health reset, a romantic getaway, or a creative sabbatical, Kelly shows you how to pick a destination that truly supports your intention.

From Greece’s healing blue zones to the quiet beauty of Costa Rica’s jungles, this episode explores how to bring more meaning to your adventures and make every trip feel like it was designed just for you.

Inside this episode:

• How to align your destination with your travel intention
• The difference between “destination-first” vs. “intention-first” travel
• How your budget shapes where (and how) you travel
• The truth about “Instagram vs. Reality” tourism
• When to travel for best experiences (low, shoulder, or high season)
• How to avoid travel stress and find destinations that match your season of life

If you’re ready to make your 2026 travels intentional, transformational, and totally aligned with you, this episode is your roadmap.

📍 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  
• 01:10 Why Destination Choice Matters  
• 02:00 How to Pick Health, Wellness, or Connection Destinations  
• 04:00 Budget, Season, and Reality Checks  
• 06:00 Avoiding Overtourism and Stress  
• 07:10 Timing, Seasons, and Restrictions  
• 08:00 How to Align Your Destination With Your Goals  
• 08:30 What’s Next: Building a Balanced Itinerary  

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 

What if your next trip could change your life, not just your location?

In this episode of Transform With Travel, we kick off the Intentional Travel Planning Series, where I share how to plan bucket-list trips that align with your goals, values, and season of life.

Discover how to plan your 2026 adventures with purpose, whether it’s a healing solo trip to Greece, a yoga retreat in the islands, or a digital detox in Sweden. I guide you through how to set travel intentions, choose destinations that match your energy, and make every journey an act of self-discovery.

Inside this episode:

• How to align your travel plans with your personal goals and values
• Turning bucket-list trips into meaningful, mindful experiences
• Why intentional travel doesn’t mean boring travel
• Real stories of transformation through travel
• How to start planning your 2026 adventures now, stress-free

If you’re craving adventure that feels good for your soul and your schedule, this series is for you.

📍 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 to Transform With Travel | What Is Intentional Travel  
• 01:30 Intentional Travel Isn’t Boring | A Healing Trip to Greece  
• 03:30 Align Your Life Goals With Travel Goals  
• 05:00 Travel for Health, Growth, and Relationships  
• 07:00 Purposeful Career Travel and Sabbatical Inspiration  
• 08:00 Hobby-Based and Joyful Travel Ideas  
• 09:20 Practical Steps to Plan Your Trip With Intention  
• 10:15 What’s Coming Next | The Perfect Destination for You   

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 

Are you ready to transform your travel experiences and maybe even your career through the world of travel?

In this episode of the Transform with Travel podcast, I sit down with Henley Vasquez, the CEO and co-founder of Fora. This conversation illuminated the evolving landscape of the travel industry, the rise of travel advisors, and the growing interest in wellness travel. 

We got into the changes in the travel industry, particularly post-pandemic. The demand for travel advisors has surged as travelers seek guidance through the more complex travel landscape. The conversation highlighted the growing need for flexibility and the ability for last-minute planning, as people are still wary of committing to travel plans far in advance.

Fora aims to revolutionize the travel advising industry by offering a modern platform that supports advisors with training, efficient booking tools, and community connection. This approach not only helps seasoned advisors but also makes it easier for newcomers to enter the field and succeed.

Henley shared some exciting travel trends, including a move towards exploring less touristy areas in popular destinations like Italy and the rise of far-flung destinations such as Bhutan. She also noted the continued popularity of domestic travel within the United States, with destinations like the American West offering unique experiences.

We talk about:

• 00:00 Intro
• 04:56 The Evolution of the Travel Industry
• 09:17 Introducing Fora: A Modern Travel Agency
• 16:25 The Power of Community in Travel Advising
• 20:12 Becoming a Standout Travel Advisor
• 22:41 The Power of Word of Mouth in Travel
• 24:02 The Rise of Wellness Travel
• 28:05 Emerging Travel Trends and Destinations
• 33:17 The Value of Local and Simple Travel
• 42:16 Final Thoughts and Becoming a Travel Advisor

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 Henley 

• https://www.foratravel.com/ 
• https://www.instagram.com/hellofora/ 
• https://www.instagram.com/henleyv/ 

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 holds an unparalleled ability to transform lives. It’s not just about the destinations visited but the personal growth and self-discovery that happen along the way. In this episode of Transform with Travel, I sit down with Gabriella Arbesu, a long-time friend and avid traveler, about the profound impacts of her travel journey.

Gabi shares the influence of her Cuban-American heritage on her identity, painting a vivid picture of growing up in a bustling and loud Cuban household against the backdrop of a quieter American culture. This duality of cultures shaped her into a bold, unapologetic individual, proud of her heritage and open to the world’s diversity.

This episode is a testament to the power of travel and personal growth. It’s a reminder that we all have the power to transform our lives through our journeys, both literal and metaphorical. I encourage you to embrace the unknown, pursue your passions, and let the world open your minds and hearts to new perspectives.

Share your thoughts: How has travel transformed you? Join the conversation and let us know your story of transformation through travel!

We talk about:

• 00:00 Intro
• 01:47 Exploring Cuban-American Heritage and Growing Up in South Florida
• 05:09 Gabby's Yoga Journey: From Trauma to Transformation
• 09:27 The Art of Holding Space: Lessons from Yoga and Retreats
• 09:53 The Impact of Travel on Personal Growth and Cultural Connection
• 29:14 Navigating Relationships and Travel: Moving to Central America
• 29:51 The Reality of Living Abroad: Challenges and Triumphs
• 35:21 Falling in Love with Nicaragua
• 36:13 The Decision to Buy Land
• 36:59 Understanding Property Ownership in Nicaragua
• 37:42 Building a Dream: From Vision to Reality
• 39:41 Exploring the Future of Yoga Retreats
• 41:57 Embracing Creativity: The OnlyFans Journey

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 Gabi

• Instagram: https://www.instagram.com/gabriella__cristina
• https://hoo.be/gabriellacristina

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

Are you yearning for an experience that could transform not just your family’s outlook on the world, but also improve your own as a parent? 

Are you curious about how different cultures parent their children? 

In today’s fast-paced, technology-driven world, the notion of slow travel can create the perfect environment for personal growth and connection. Join Elodie Ferchaud, co-founder of Boundless Life, and I as we navigate the world of travel for families.

Elodie’s journey started out as an expat family, where she observed the differences in parenting across cultures - Swedish, French, Japanese and American. Because of this cross-cultural experience, she was able to blend the best of all 4 parenting styles into her own version of mothering.

Boundless Life stands out with its thoughtfully crafted communities in places like Greece, Portugal, and Bali, aiming to provide holistic family living solutions. These include schooling based on experiential learning and tight-knit support networks for parents and children alike. 

Boundless Life’s approach to education is innovative, emphasizing growth mindset and holistic child development through modular, multi-age learning environments. Kids not only partake in culturally immersive activities but also benefit from stable, supportive learning surroundings that mitigate the transitions typically associated with frequent relocations. 

We talk about:

• 00:00 Intro
• 03:08 Parenting Across Cultures
• 08:23 Elodie's Expat Life Before Boundless Life
• 24:39 Living the Boundless Life: Experiences in Portugal, Greece, and Bali
• 28:00 The Impact of Travel on Parenting and Personal Growth
• 32:21 Boundless Life Program Details and Flexibility
• 33:44 Traveling with Familiar Faces
• 34:13 Creating a Consistent Learning Environment
• 35:21 The Benefits of Multi-Age Learning
• 37:53 Growth Mindset in Education
• 38:50 Parental Growth Through Travel
• 45:11 The Power of Community in Parenting
• 50:13 Joining Boundless Life
• 53:52 Future Plans for Boundless Life

Resources & Links:

• Ready for your next adventure? Click here to view our Trip Planning Packages & 2025 Pricing: https://transform-with-travel.captivate.fm/packages
• Bringing Up Bébé: https://a.co/d/hz9QYTB  
• There’s No Such Thing As Bad Weather: https://a.co/d/9sp4ZI2 
• French Children Don’t Throw Food: https://a.co/d/10wtCy7 

Connect with Elodie

• Instagram: www.instagram.com/boundlesslife 
• https://www.boundless.life/

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 

Are you ready to transform your travel experiences into moments of depth and personal growth? In today's fast-paced world, travel has become more than just checking destinations off a list. It's about immersing yourself in new cultures, embracing challenges, and living with intention. This concept of intentional travel was the highlight of our recent conversation with Kelly Fischer.

Traveling often promises the allure of adventure and the temptation of Instagram-worthy spots. Yet, as Kelly shares, it's about the deeper experiences found beyond the crowded tourist traps and social media snapshots. These are the moments where you find yourself truly present, whether you're savoring a buttery croissant in France or navigating an unknown village in northern Italy.

Kelly's adventures highlight how stepping into the unknown isn't just about seeing new places; it's about personal growth. Surrounded by the unfamiliar, she found a deeper trust in herself and an ability to embrace the unexpected twists of travel. Her story reminds us that even the journey itself, with all its challenges and surprises, is just as rewarding as the destination.

We talk about:

• 00:00 Intro
• 03:25 Building Conscious Brands
• 05:58 Living with Depth and Presence
• 12:39 Kelly's Journey to Italy
• 15:38 Embracing Uncomfortable Growth
• 19:40 The Value of Intentional Travel
• 24:22 Advice on Taking Leaps of Faith
• 26:36 The Power of Curiosity and Learning
• 28:33 Living in the Present Moment
• 32:03 Maintaining Wellness Routines While Traveling
• 34:50 The Concept of Pocketing Experiences
• 41:24 Rapid Fire Travel Questions

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 Kelly Fischer:

• Website: www.depththeory.com 
• Instagram: www.instagram.com/depththeory 

Connect with Kelly

• 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

Are you willing to step into the unknown to bring your dreams to life? In this episode of the Transform with Travel podcast, I had an enlightening conversation with Marisa Folz McConnell, a visionary entrepreneur behind The Wander Shop. 

The Wander Shop was born out of Marisa's love for travel and fashion. Initially envisioned as a mobile store, Marisa's ingenuity and grit saw it evolve into a lifestyle boutique that supports local brands and artisans. With every change in her business model, from pop-up events and roaming Airstreams to stable retail locations, Marisa demonstrates the importance of flexibility and intuition in entrepreneurial success.

Travel has been a major influence on Marisa's fashion sense and business ethos. She draws inspiration from California’s laid-back style and Italy's classic elegance, incorporating versatile, timeless fashion pieces in her store. Trend forecasting for 2025 sees the return of baggy jeans and bold colors, and Marisa advises building a capsule wardrobe that balances the trendy with the timeless.

Marisa's story is a reminder to trust your instincts and seize opportunities when they arise. Her willingness to embrace risks and adapt to new circumstances offers a valuable lesson for anyone looking to transform their vision into reality.

We talk about:

• 00:00 Intro
• 04:50 The Origin of The Wander Shop
• 08:14 Challenges and Evolutions
• 09:43 Embracing Change and Growth
• 11:17 Balancing Routine and Spontaneity
• 23:10 Travel Influences and Style
• 25:56 Packing Tips for Overpackers
• 28:16 Photo Tips and Background Remover
• 28:33 Packing Strategies and Outfit Planning
• 29:33 Content Creation and Brand Building
• 30:20 Revisiting Favorite Travel Destinations
• 38:38 Planning the Perfect Girls Trip
• 43:40 Fashion Trends for 2025
• 46:08 Running a Small Business

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 Marisa

• Instagram: https://www.instagram.com/tothewandershop 
• TikTok: https://www.tiktok.com/@tothewandershop 
• https://thewandershop.com/ 

Connect with Kelly

• 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 

In this milestone 100th episode of Transform With Travel, we highlight the transformative power of travel in shaping lives, relationships, and legacies while acknowledging the resurgence of travel post-pandemic and its associated challenges like overtourism and stressed ecosystems. 

We talk about the role of travel advisors in promoting sustainable and responsible travel choices, aiming to shift from being mere consumers to stewards of travel. As we look forward to the future, I hope for more intentional, community-supportive, and culturally preservative travel.

Thanks for tuning in and celebrating 100 episodes, here’s to the next 100!

We talk about:

• 00:00 Intro
• 01:11 The State of Global Travel Post-Pandemic
• 01:30 The Impact of Overtourism
• 02:28 Responsible Travel Choices
• 03:22 The Role of Travel Advisors
• 04:35 Future of Travel and Podcast Vision
• 05:38 Final Thoughts 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 Kelly

• 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 

Have you ever wondered what it's like to view the world from the cockpit of an airplane? Or perhaps you're one of the many travelers who experience a tinge of anxiety every time you buckle up for a flight. In today's episode, we unravel these mysteries with insights from a seasoned pilot, Simon Brackett, and learn practical ways to manage in-flight anxiety.

Travel can open up new perspectives and enhance the quality of our lives. Traveling can be transformational, however, for many, stepping on an airplane introduces a wave of nervousness, often due to turbulence or unfamiliar sounds during a flight. Understanding the process and realities of flying can ease anxiety, allowing one to fully embrace the adventurous spirit that travel promises.

One of the most common fears associated with flying is turbulence. Simon Brackett, a commercial pilot and former Air Force special operations pilot, clarifies that turbulence doesn't mean danger. He compares it to a boat riding over choppy water — uncomfortable but manageable. Simon reassures us that he's never encountered structural damage to an aircraft due to turbulence. He also shares his best tips for staying safe, as well as for managing flight anxiety.

Understanding the mechanics and safety of flying, coupled with mindful practices, can vastly improve your travel experience. Embrace these tips and insights next time you embark on your journey, and remember to keep exploring the horizons, grounded in the confidence of a safe flight.

We talk about:

• 00:00 Intro
• 00:50 Coping with Flight Anxiety
• 05:36 Understanding Flight Safety
• 11:25 Simon Brackett's Aviation Journey
• 18:43 The Reality of Turbulence
• 25:31 Seatbelt Safety Explained
• 33:44 Overcoming Claustrophobia on Flights
• 34:53 Understanding Flight Delays
• 39:21 Pilot Communication Styles
• 42:38 Traveling with Young Children
• 45:49 Addressing Passenger Concerns
• 50:07 The Joys of Being a Pilot
• 54:20 Travel Tips and Life Lessons
• 01:05:41 Conclusion and Next Steps

In this episode:

• Episode 43: https://transform-with-travel.captivate.fm/episode/043-how-yoga-and-meditation-can-help-you-become-a-better-traveler-with-justin-liebman 

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 Kelly

• 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