The Question Everyone Asks
Favorite moments, quiet lessons, and what travel taught me
#39
One of the questions we’re asked again and again — especially after our first six-month adventure — is: What was your favorite place?
For Tim, the answer is easy. Costa Rica. The beaches, the water, the expansiveness. It was also the place where he had one of the most profound, personal experiences of the entire journey — a single day at the beach that opened something deep and lasting for him.
For me, it’s never been one place.
It’s moments. Snapshots. Experiences. The way something lands in my body and stays there.
And that was true again during this most recent chapter in Europe.
On our very first date, Tim asked me what my favorite city in the world was. I answered without hesitation: Rome. I grew up Italian, deeply connected to my mother’s heritage, and Rome was the place I’d traveled to most often over the years. Tim had never been, and getting to share that city with him felt like a dream come true.
And yet — interestingly — while Rome was beautiful and meaningful, it didn’t end up being one of my biggest highlights.
That’s the thing about growth. As we change, so does what resonates with us.
One of my most memorable moments this time around came on the Greek island of Serifos — and it’s a bit of a paradox. I have a video of it. It’s dramatic. Powerful. Visually stunning. And yet… it’s not a day I go back to often in my heart.
That day, I walked seven to eight miles across the island — from one side to the other, climbing all the way up to a church perched high on the hill. Midway through, I was hit with a massive thunderstorm and torrential rain. And at the end of it all, something extraordinary unfolded — a moment so full of awe and joy that it’s all captured on film, my voice filled with wonder as it happened.
That walk has become a metaphor for how I see life.
The road felt long. The conditions were unpredictable. There were moments when turning back would have made sense. But I stayed open — to shortcuts, to guidance, to ease where it was offered. I asked Spirit for direction. And even through the storm, I reached the top and received far more than I could have imagined.
That morning, Tim wanted a beach day to himself. I asked myself a simple question: What would make me happiest today? I looked across the horizon, saw the church I’d been curious about for days, packed a small backpack with water and snacks, pulled on a swimsuit and cover-up — and just went.
No overthinking.
No perfect plan.
Just movement.
We can live our lives this way, too.
We don’t always need to analyze every step or wait for certainty. When something lives in your heart, it’s because it wants to become real. Sometimes the most powerful thing you can do is simply say yes — and take the first step.
That same energy guided my move to Texas.
Even after I shared it, many people didn’t quite believe it was actually happening. And sure — when I arrived, I hit an unprecedented week-long snowstorm. You could argue that was proof it wasn’t the right move.
I see it differently.
Life will always happen. Delays will arise. Conditions won’t always cooperate. That doesn’t mean you chose wrong — it means you’re being asked to meet the moment with grace.
So I made soup. I rested. I learned my new job. I adjusted.
After ten months of travel in fifteen months, being snowed into a cozy apartment felt… glorious. Not having to move. Having a gym downstairs. Letting my nervous system land.
That pause gave me time to research and purchase a new car — something Tim and I had talked through together before parting ways. A dear friend of his, who lives nearby, spent an entire day helping me navigate the logistics. I didn’t have to do it alone. It was another reminder of how supported I am — and how life meets us when we allow it to.
I named the car White Light. 🤍
When I look back on this adventure, one of the things I’m most grateful for is how well Tim and I traveled together. The first six months we ever traveled, we were figuring everything out in real time. I had just lost my job. Money felt uncertain. We hadn’t lived together before. And I was carrying one too many bags — which feels like a metaphor for life back then.
This time, things were different. More settled. More intentional. More partnership. And that made all the difference.
Some moments that will stay with me forever include standing inside the Sistine Chapel and Vatican again, feeling the weight of history resonate in my cells; early mornings in Paros, walking painted cobblestone streets to the bakery as the town slowly woke up; and Christmas in Sardinia — twinkling lights, ancient streets, and the most incredible seafood antipasti platter on Christmas Eve.
That’s what travel gives us.
Memories we carry forward.
Moments that soften us.
Stories that live inside our hearts long after we’ve moved on.
And if you’re curious to see the walk that became one of my greatest metaphors — you can watch that favorite video of climbing to the top of the hill over on the travel channel.
Blessings and highest and best for a beautiful week.
To your highest and best,
Dianna
💌 Love this story? Want more like it — straight to your inbox?
Join the Travels With Spirit newsletter for soulful travel, personal growth, and freedom-filled inspiration.