Traveling with My Parents

How Traveling with My Parents as an Adult Brought Us Closer

By Jessica Monroe
Bridging generations through shared sunsets, stories, and long walks.

The Decision to Go (and the Doubts That Came With It)

It started with a text from my mom: “Dad and I are thinking about doing a little trip this fall. Want to join?”

I stared at my screen longer than I care to admit. I loved my parents, truly—but the idea of spending a week with them as an adult, in shared hotel rooms or over long dinners with no escape route, gave me pause.

Still, something inside me said yes. Maybe it was nostalgia. Maybe it was guilt. Maybe it was the realization that time was slipping faster than I cared to admit. So I replied, “Count me in.”

We picked Italy. My dad’s grandparents were from near Florence. My mom had always dreamed of seeing the Amalfi Coast. I figured if we were going to do this, let’s make it a bucket-list-worthy experiment.

New Roles, Old Rhythms

From the first airport coffee to the final train ride, the experience felt surreal. Suddenly, I was the one booking tickets, navigating train schedules, and handling the language barrier. I wasn’t the kid anymore. And yet, our old roles crept in.

My mom still reminded me to put on sunscreen. My dad still tried to carry my bag—even when I told him three times I had it. But there was something softer about it now. Less parental control, more instinctual care.

And slowly, something shifted in me, too. I started seeing them not just as my parents, but as people. Two humans who had lived, and loved, and worried, and made mistakes long before I ever entered the picture.

The Power of Unscheduled Time

Some of my favorite moments weren’t the major sights. They were the slow mornings sipping espresso on our Airbnb terrace. The meandering walks down cobblestone alleys where we’d peek into quiet courtyards and speculate about who lived there.

In Positano, we sat in silence watching the sun melt into the sea. My dad said, “I never thought I’d see this in real life.” My mom just held his hand.

That moment cracked something open in me. I saw their wonder. I saw their gratitude. And I saw myself in both of them—in the way I chase beauty, in the way I hold on to people.

Conversations That Wouldn’t Have Happened at Home

Travel peeled away the layers. Without the distractions of everyday routines, we had space for conversations that went deeper than “How’s work?” or “What’s new?”

Over wine in Florence, my mom told me about a solo trip she took in her twenties. I had never heard the story before. In Rome, my dad admitted he wished he had taken more risks earlier in life.

And one night, while we shared a bottle of limoncello, they asked me questions—not like parents monitoring a child, but like friends genuinely curious about my thoughts, my fears, my dreams. I answered honestly.

The Minor Meltdowns (and Why They Didn’t Matter)

Of course, it wasn’t all dreamy. We got lost. My dad misplaced his passport for an entire hour. My mom cried when she couldn’t figure out how to use the hotel’s European-style coffee machine. I snapped once when they wouldn’t stop debating which turn to take.

But those moments passed. Because we weren’t just navigating a country—we were navigating each other. And the grace we gave one another, despite the imperfections, made everything more real. More human.

Coming Home with Something New

When we got back, something had shifted. We didn’t talk every day, but when we did, the conversations felt richer. I found myself texting my mom for her risotto recipe. I sent my dad photos of sunsets that reminded me of Italy.

And I noticed I felt closer to them—not just because of the trip, but because of who we had allowed ourselves to be while traveling. Vulnerable. Curious. Open.

We hadn’t just visited Italy. We’d rediscovered each other.

Go Now, Not Later

If you’ve ever considered traveling with your parents as an adult—do it. Don’t wait for the perfect time. Don’t wait for the big occasion.

Go before you think you’re ready. Because there’s something sacred about watching your parents marvel at the world. And there’s something healing about letting them see the adult you’ve become.

You won’t regret the missed buses or awkward hotel breakfasts. But you might regret the chance not taken.

Have you traveled with family in adulthood and found unexpected closeness? Share your story with @AffordableJourney using #GenerationsOnTheGo.