Choosing Travel Based on Your Emotional Season
How to plan trips that support how you actually feel—not how you think you should feel
We tend to plan travel around logistics: time off, flight prices, school calendars, bucket lists. What we rarely ask—before clicking “book now”—is a much simpler question:
How am I actually feeling right now?
Because here’s the thing no one tells you: the same destination can feel wildly different depending on the emotional season you’re in. A packed itinerary might feel exhilarating one year and utterly exhausting the next. A quiet beach might feel boring—until it feels like exactly what your nervous system has been asking for.
Psychology backs this up. Research on stress, novelty, and emotional regulation suggests that our capacity for stimulation changes depending on what we’re carrying internally. In other words, travel isn’t inherently restorative. Alignment is.
Over the years, I’ve learned that the most meaningful trips weren’t the most impressive ones—but the ones that matched the season I was in.
What Do I Mean by an “Emotional Season”?
An emotional season isn’t a diagnosis or a permanent identity. It’s a snapshot. A chapter. A state of being shaped by life circumstances—connection, grief, curiosity, burnout, growth.
When we choose travel that supports that state instead of fighting it, something shifts. Travel stops being an escape and starts being a companion.
Here’s what that’s looked like in my own life.
A Season of Connection: Sardinia
Some trips are about seeing a place. Others are about being welcomed into it.
Our time in Sardinia was firmly a season of connection. We traveled there with neighbors who are originally from the island, and instead of following a guidebook, we followed people. They showed us their Sardinia—introducing us to family, friends, local traditions, and places we never would’ve found on our own.
We didn’t just visit; we belonged. We celebrated their mother’s 70th birthday surrounded by laughter, food, stories, and that unmistakable feeling of being folded into something meaningful.
Psychologically, connection is one of the strongest buffers against stress. Research consistently shows that shared experiences—especially novel ones—deepen relationships and enhance emotional well-being. Sardinia wasn’t about ticking boxes. It was about being known. And that made it unforgettable.
A Season of Growth: Switzerland
Switzerland marked a milestone in more ways than one. It was my 50th birthday—and the first big international trip Bryan and I took without the kids.
There was excitement, of course. And also tenderness. I missed them. But there was something quietly profound about rediscovering how we travel together—how we explore, wander, talk, and simply be—the way we did before parenthood expanded our world.
It felt full circle. Growth often does.
Developmental psychology tells us that novelty paired with emotional safety supports identity expansion. This trip wasn’t about reinvention; it was about remembering. Growth doesn’t always mean adding something new. Sometimes it means returning to a version of yourself with more wisdom in your pocket.
A Season of Grief: Virginia Beach
After my father died, I didn’t need adventure. I needed calm.
At the time, we lived in Virginia, but I grew up in Florida, and the beach has always been my place of emotional regulation. So even though I was far from home, I found my way back to water.
Virginia Beach became a place to breathe. Quiet walks. Sunsets that didn’t ask anything of me. Journaling by the pool. Naps when the grief felt heavy. It was a low-maintenance trip for a healing heart.
Grief research is clear: environments that reduce sensory load—gentle rhythms, natural settings, predictable routines—can support emotional processing. That trip didn’t fix my grief. But it held it. And sometimes, that’s enough.
A Season of Burnout: Cruises
When we’re burned out, decision fatigue is real. And this is where cruises shine for us.
No cooking. No planning every meal. Teenagers with endless entertainment. Parents with access to a quiet, adults-only pool area. When burnout is the season, we skip excursions entirely. While others are rushing around ports, we lean into the quieter ship—reading, resting, floating, doing absolutely nothing impressive.
From a nervous-system perspective, this matters. Burnout thrives on chronic demand. Removing decisions and responsibilities—even temporarily—allows the body to downshift. Cruises aren’t about exploration for us in those seasons. They’re about relief.
A Season of Curiosity: Italy
Italy was curiosity in its purest form—and it was different for each of us.
Bryan was drawn to the history. I couldn’t get enough of the culture. Callan was all in on art and museums. Jake had his heart set on seeing the Colosseum underground, learning about gladiators. And Max? Southern Italy, beaches, and an endless supply of gelato.
Every curiosity was fed. And that’s the magic of choosing travel during a season when your emotional bandwidth for learning and stimulation is high.
Psychological research on curiosity shows that it enhances memory, engagement, and satisfaction. When we travel curious—not rushed—we don’t just see more. We absorb more.
Italy met us exactly where we were.
Choosing Travel That Fits the Season You’re In
Before planning your next trip, try asking yourself:
Do I want rest, connection, growth, or stimulation right now?
How much decision-making can I realistically handle?
What pace would feel supportive—not aspirational?
What would “enough” look like on this trip?
There is no universally healing destination. There is only alignment.
The Quiet Truth About Meaningful Travel
The trips that stay with us aren’t always the ones that look best on social media. They’re the ones where we felt seen—by others, by ourselves, by the moment we were in.
Choosing travel based on your emotional season isn’t about lowering expectations. It’s about choosing wisely. Listening closely. And trusting that how you feel matters just as much as where you go.
And maybe more.
