What I Learned from a Once-in-a-Lifetime Sibling Trip

In June, I went on an unforgettable trip to Greece with my brother and sister.✈ No spouses, no kids—just the three of us. Six days, six nights. It was something we had dreamed about and planned together, and it turned out to be even better than I imagined.

We ate, we drank, we drove across stunning landscapes, and we explored so many beautiful places. But more than anything, we connected. It was the kind of experience that stays with you, and I’ve been reflecting on a few things I learned along the way.

Lesson One: I’m so lucky ☘

Lucky that I could afford the trip. Lucky that my husband and kids supported me disappearing at a very chaotic time of year. Lucky that my siblings carved time out of their own busy lives to say yes to a shared adventure. That kind of support and flexibility is not something I take for granted. I know how rare it is—and how meaningful.

Lesson Two: Same family, totally different people

If I had to describe us, I’d say I’m the Disney princess of the group. I like nice hotels, great meals, and the occasional pampering. My sister? She’s more the adventurous, hike-into-the-wilderness, sleep-under-the-stars type. My brother is a true mix of both, happy to glamp one night and enjoy a luxury dinner the next.

I was worried those differences might cause tension. I imagined debates about where to stay, what to do, or even how early to get up. But something beautiful happened. We didn’t clash. We adapted. We appreciated each other’s quirks. We leaned into what made each of us unique, and somehow that made the trip even better. Our bond grew stronger, not in spite of our differences, but because of them. 

Lesson Three: My body needs better travel support 🛏

I’ll just say it—my neck hated this trip. The charming little beds and European pillows did me no favors. Long flights and long car rides added to the strain, and I came home realizing I need to care for my body like it’s going with me on every trip—which it is. The adventure was incredible, but nothing felt better than being back in my own bed. I’ve already invested in a very cute memory foam travel pillow for future trips. This is 50, apparently.

Lesson Four: I’m a proud overpacker

Let’s just say... I haven’t changed. If you’ve read my past blog post about packing (link here), you know I struggle with it. The anxiety, the last-minute decisions, the sheer volume of “just in case” items. I overpacked again: checked bag, carry-on, backpack, but I didn’t feel guilty about it. I gave myself permission to pack the way I needed to, and honestly, it was the best choice ever. I used my beloved packing cubes. I took pictures of what worked (and what didn’t). I even made a list for next time. But I still overpacked, and I’m standing by it. 😊

Lesson Five: I am loved 💕

This trip was part of my 50th birthday celebration and reaching that milestone gave people a reason to reach out. Friends, family, colleagues—all shared memories, kind words, and heartfelt wishes. For someone like me, an ADHDer who tends to forget the positive, it was a powerful reminder that I’m not alone. That I’m surrounded by people who care.

If you’re one of the people who reached out—thank you. And if you meant to but forgot (because... ADHD), I still know you love me. And I love you right back.

There are more stories I could share, and maybe I will. But for now, I’m grateful for the memories, the lessons, the laughter, and the reminder that love and connection show up in many different ways; including overpacked suitcases, aching necks, and a makeup bag I didn’t use once.

Even though I’ve been calling this a once-in-a-lifetime trip, I really hope it wasn’t. I hope we find a way to travel together again.🙂

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