Episode 79

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Published on:

6th May 2025

079: 3 Ways Parents Self-Sabotage Their Family Vacations (And What to Do Instead)

Ever felt more frazzled than fulfilled during a family trip? You're not alone—and you're definitely not failing.

In this solo episode, host Kelly Tolliday pulls back the curtain on the three sneaky ways parents unintentionally sabotage their own family travels. From luggage that could double as a moving van to itineraries tighter than your kid’s shoes after a growth spurt, Kelly’s calling out the chaos—and offering kinder alternatives.

If you've ever packed “just in case” and ended up schlepping “never used,” this one's for you.

In this episode, Kelly shares:

  • Why packing everything but the kitchen sink sets you up for stress, not success
  • How overstuffed itineraries rob your family of joy, connection, and spontaneous magic
  • The myth of the “perfect” family vacation—and how releasing it gives you the freedom to actually enjoy your trip
  • Real talk and practical tips to make travel smoother, lighter, and way more fun for everyone

Whether you're prepping for your first big trip with kids or you're a seasoned nomadic parent wondering why it still feels hard, this episode will help you shift from surviving your travels to actually transforming through them.

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Don’t forget to subscribe, rate, and review Transform With Travel. Happy travels in 2025! ✈️

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About the Podcast

Transform With Travel
Go On An Adventure
Welcome to the Transform with Travel Podcast, where we share stories of personal transformation and life lessons through our experiences of traveling and exploring the world. We believe travel has the power to transform your life, one trip at a time. So we bring on every day adventurers to tell their stories of inspiration, as well as Industry Experts to enhance and optimize your travels. I’m your host - Kelly Tolliday, Founder of Transform With Travel - and it’s my mission to inspire you to live life to its fullest, travel with an open-mind & Heart, and let the world show you a new perspective.

About your host

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Kelly Tolliday

Kelly is the Founder of Transform With Travel, with over 11 years in the travel industry. She's a Wellness Travel Expert, Retreat Facilitator, Travel Advisor & Podcast Host.

She's also a 500-Hr Registered Yoga Teacher & an Accredited Continued Education Provider for the Yoga Industry.

She's traveled to over 45 countries and lived across 4 continents. Now, it's her mission to inspire and support you in stepping outside of your comfort zone and into the life of your dreams.

She's passionate about immersive and transformational travel. She believe when you travel with intention, by combining wellness, adventure & cultural enrichment, you can truly transform your life, one trip at a time.

She's now based in South Florida, and she's married to her husband Sam with 2 beautiful daughters & 2 crazy dogs.