Some of the most unforgettable travel moments I’ve had didn’t happen at top-rated attractions or in front of famous landmarks. They happened in small shops, on sidewalks, and during ordinary moments that didn’t look like much at the time—but stuck with me.
Traveling with heart means going beyond the itinerary. It means not just visiting, but connecting. With people. With places. With your own presence.
Truthfully? I’m still learning how to do that. But one of the best teachers has been Tom.
1. Let Go of the Checklist (This One’s for Me)
I’m a planner. I love a good checklist, a well-mapped route, and the satisfaction of “we did it all.” But Tom? He slows me down—in the best way.
He doesn’t rush through a town just to hit the next destination. He talks to shop owners. He asks strangers about their dogs. A simple walk through a few shops becomes an opportunity for connection. And honestly? He’s right. That’s where the real stories happen.
So now, I’m trying to leave space in our plans. Room to meander. Room for a long conversation or a quiet bench. I don’t always get it right, but I’m better than I used to be.
This shift reminds me of what I wrote about in Redefining Success—sometimes doing less leads to something deeper.”
2. See People, Not Just Places
One of the biggest mindset shifts I’ve made is remembering that every place is someone’s home. The barista, the vendor, the person passing by with their kid or their dog—they’re part of the experience if you choose to engage. And research shows connecting with locals makes travel more memorable.”
Small talk isn’t something that comes naturally to me, but Tom’s a natural. He’ll strike up a conversation anywhere. And when I follow his lead? It’s almost always worth it. I walk away reminded that travel isn’t just about where you go—it’s about who you meet.
Like the couple who ran a little gift shop in Lauderdale-by-the-Sea—we stopped in just to browse, but ended up talking with them for nearly 30 minutes. We talked about their shop, the town, a little about life. By the time we left, it almost felt like we were saying goodbye to friends. It wasn’t planned. It wasn’t flashy. But it’s one of the things I remember most vividly from that trip.
Those are the moments that stay with you.
3. Find a Local Rhythm
One thing I’ve started doing on trips is picking just one local habit to adopt. Morning coffee with a view. A walk at the same time every day. A favorite spot to sit and reflect and maybe a little people watching.
It gives the trip some rhythm—and gives me something to come back to. A familiar moment in a brand-new place. And sometimes, that’s what makes a place feel meaningful.
4. Take the Photos—Then Write a Little, Too
Let’s be real—I take a lot of photos. I love capturing moments, views, food, scenery, all of it. But I’ve started adding something new: journaling.
Just a few lines—what we saw, how it felt, what I want to remember later. Sometimes I write it in my travel journal, sometimes it’s just a note on my phone. But those little reflections help me slow down and remember the feeling of the moment, not just the image. You think you will remember everything but you won’t. Write it down!
Rick Steves calls it ‘the zen of journaling’—a simple way to be more present and capture what really matters as you travel. His take on it is worth a read.
5. Embrace the In-Between Moments
Some of my favorite memories now are the ones that never made the highlight reel. Sitting with Tom after walking all day. Watching people stroll by. Laughing over something small. Stopping just to sit and breathe. I used to think travel had to be big to be meaningful. Now I know: the quiet parts matter too.
Final Thoughts: Travel Isn’t Just About Going Somewhere—It’s About Being There
I’ll probably always love my lists. But thanks to Tom—and to practice—I’m learning to leave space for the unexpected. The best part of the trip might be the place you almost skipped, the person you almost didn’t talk to, or the hour you spent doing nothing at all.
That’s the heart of it.
So next time you pack your bags, don’t just plan the trip. Make space for connection, curiosity, and being right where you are.