Travel has a magical way of touching our lives, often leaving an imprint far deeper than we realize at the moment. Sometimes, it’s a single trip that shapes our dreams, inspires our paths, and ignites a lifelong passion. At The Shameless Tourist, we’re guided by these transformative journeys, each uniquely powerful and deeply personal. Today, we’re excited to share the stories behind the trips that changed our lives, featuring stories from three of our extraordinary team members. These legacy journeys not only shaped their love for exploring the world but also sparked the desire to create unforgettable, pinch-me experiences for others. Join us as we reflect on those life-changing moments that remind us why we travel, why we share our passion, and why we’re committed to turning your ‘I wish’ into a lasting ‘Remember when.’
I still remember my first trip to Walt Disney World in 2002. My mom had called to make the reservation over the phone, because that’s how it worked back then, and the Cast Member told her, “You’ll want to book a Cinderella’s Royal Table reservation.” So she did. That was the full extent of our Disney planning.
It was me at six years old, my mom, my aunt, and my two-year-old cousin. We showed up bright-eyed and completely overwhelmed. No idea how to get from
park to park, what to prioritize, or how to do anything efficiently… but we still felt the magic.
I remember Mickey ice cream bars and watching the parade like it was the most incredible thing I’d ever seen. And I also remember my mom saying she wanted a do-over.
So we went again. And again. And again after that. Somewhere along the way, I realized I never wanted another mom to show up unsure of what to do or how to make the most of it. That very first trip? It’s the reason I became a travel agent specializing in Disney destinations. The magic is real, and it’s a whole lot easier to enjoy when someone’s guiding you through it.
As a travel advisor, I plan every detail to make your trip seamless and unforgettable. But things don’t always go as planned. And yet, it’s often those imperfect moments that bring the most unexpected beauty.
Our own family vacation to Maui was the perfect example. It wasn’t flawless—but it was rich, meaningful, and beautiful in so many ways.
We played hard at the beach and the pool, and we worked hard too—some of us logging early morning hours before the rest of the island was even awake.
We pushed outside our comfort zones. We supported each other, got frustrated with each other, and found moments of grace and forgiveness when our expectations didn’t match reality. There were indulgent moments—spa visits, rounds of golf—and there were meaningful conversations that spanned generations.
This trip reminded me that the most memorable vacations aren’t always the most “perfect”—they’re the ones that stretch us, connect us, and reveal something new.
When I think legacy trips, I immediately think of a cross-country road trip my family took in 2016, hitting 12 national parks. The time we spent together on the road, seeing some of the USA’s most beautiful landscapes and diversity, was incredibly valuable.
At the time, I was a pouty teenager who would’ve much rather spent my summer at the pool with friends, and boy did I put up a fight. But the wonders I saw and the time with my family have only grown more meaningful with time.
Some of my favorite memories are from that trip—stargazing in the wilderness, doing a ropes course with my dad, and reading books out loud to my siblings. I loved that we didn’t have to leave the country to find those special moments together. This trip was foundational when I think about the beginnings of my love for travel, nature, and connecting with this place we call home, even if I only came to recognize its significance in hindsight.
Each of these legacy trip stories beautifully illustrates the profound impact that travel can have—shaping dreams, inspiring life paths, and igniting enduring passions. Every journey is an opportunity to connect deeply with the world and those we love most. Ready to plan your next journey? Let’s turn your travel dreams into timeless memories!
