How to Plan Your Dream “Bucket List” Trip in 2026 + the Power of Travel to Transform with Kelly Tolliday
What if the key to planning your dream trip isn't choosing the right destination, but first figuring out what you actually need right now in your life?
Kelly Tolliday is the founder of Transform With Travel, a professional travel advisor and wellness travel expert with over a decade of industry experience, a retreat facilitator and 500-hour registered yoga teacher, and a podcast host. She has traveled to more than 45 countries and lived across four continents, including extended time in Australia, Thailand, and Costa Rica.
In this episode, Kelly walks through the step-by-step system she uses to plan bucket list trips and how anyone can apply the same framework to start planning their own dream trip today.
Kelly reframes the entire planning process in a way that most of us haven't considered, and it changes not just where you end up going, but how you show up when you get there. She also makes a strong case for why the best travel experiences often come from letting go, even when every instinct is telling you to hold on tighter. You'll not only get Kelly's framework, but destination recommendations and a call to action at the end that I hope you follow through on.
What's one destination that's been sitting on your bucket list for way too long, and what's actually been stopping you from booking it? I'd love to hear what they are, and I hope you’ll share them by sending me an audio message.
Tune In To Learn:
Why asking "what do I need right now?" is the most important first question in trip planning
How to use urgency as a real planning tool, and why some destinations carry a genuine now-or-never factor
Why mapping out your full route, including transfer time and cost, is often the step that saves the most money
How slow travel creates more space for the unscripted moments that people end up talking about for decades
Why booking independent, locally-owned tour operators almost always leads to more memorable experiences than going with the bigger names
How to approach accommodations with a "sense of place" mindset
Advice on when hiring a professional travel advisor makes sense versus planning a bucket list trip on your own
Why we both agree that physically demanding adventures should move to the top of your list sooner rather than later
Hidden gem destinations worth visiting now, including a little-known Thai island that has somehow stayed off the radar
How to reset your mindset when things go sideways on a trip
And so much more
Resources:
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Live Your Bucket List w/ Ryan Jacobson
Curiosity As Your Travel Guide + Exploring Overlooked Destinations with John McKenzie
7 Must-Visit Destinations for 2026 (Get There Before the Crowds Arrive!) with Lyn Hughes
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Kelly Tolliday is the founder of Transform With Travel, a professional travel advisor and wellness travel expert with over a decade of industry experience, a retreat facilitator and 500-hour registered yoga teacher, and a podcast host. She has traveled to more than 45 countries and lived across four continents, including extended time in Australia, Thailand, and Costa Rica.
In this episode, Kelly walks through the step-by-step system she uses to plan bucket list trips and how anyone can apply the same framework to start planning their own dream trip today.
Kelly reframes the entire planning process in a way that most of us haven't considered, and it changes not just where you end up going, but how you show up when you get there. She also makes a strong case for why the best travel experiences often come from letting go, even when every instinct is telling you to hold on tighter. You'll not only get Kelly's framework, but destination recommendations and a call to action at the end that I hope you follow through on.
What's one destination that's been sitting on your bucket list for way too long, and what's actually been stopping you from booking it? I'd love to hear what they are, and I hope you’ll share them by sending me an audio message.
Tune In To Learn:
Why asking "what do I need right now?" is the most important first question in trip planning
How to use urgency as a real planning tool, and why some destinations carry a genuine now-or-never factor
Why mapping out your full route, including transfer time and cost, is often the step that saves the most money
How slow travel creates more space for the unscripted moments that people end up talking about for decades
Why booking independent, locally-owned tour operators almost always leads to more memorable experiences than going with the bigger names
How to approach accommodations with a "sense of place" mindset
Advice on when hiring a professional travel advisor makes sense versus planning a bucket list trip on your own
Why we both agree that physically demanding adventures should move to the top of your list sooner rather than later
Hidden gem destinations worth visiting now, including a little-known Thai island that has somehow stayed off the radar
How to reset your mindset when things go sideways on a trip
And so much more
Resources:
Sign up for our FREE newsletter
Transform with Travel
Want More?
Live Your Bucket List w/ Ryan Jacobson
Curiosity As Your Travel Guide + Exploring Overlooked Destinations with John McKenzie
7 Must-Visit Destinations for 2026 (Get There Before the Crowds Arrive!) with Lyn Hughes
Thanks To Our Sponsors
Earn Cash Back and rewards on nearly every purchase with Rakuten.
Learn more about your ad choices. Visit megaphone.fm/adchoices