From Mid-Year Reset to Tuscan Trails: How a Wedding Conversation Sparked an Intentional Adventure
If you read my last blog post on planning a Mid-Year Reset, you know I’m a big believer in creating space—mentally, emotionally, and sometimes physically—to reconnect with your values and realign your goals.
Well, this summer, I took my own medicine—literally to the hills of Tuscany.
What started as a casual conversation at a wedding table turned into a weeklong walking journey through Val d’Orcia, a quiet, sun-soaked valley in southern Tuscany. It gave me more than just scenic beauty. It gave me clarity.
Not just about hiking, but about vision, decision-making, and building a life that feels good to live in.
A Wedding, a Whisper, and the Spark of a Vision
Back in January, my husband John and I attended the wedding of a dear friend’s daughter in Vermont. We were seated with a small group of guests from different chapters of our lives—some I hadn’t seen in years.
As we shared stories and updates, the conversation shifted to summer travel plans. I didn’t have any.
But one woman at our table—a powerhouse immigration attorney and longtime single mom—shared something that lit a fire in me. Every summer, she rents the same villa in Tuscany for two weeks to completely unplug, recharge, and reconnect with herself and the people she loves. She created this annual tradition not only for her own restoration, but to offer her family and friends a space to slow down and experience this slice of heaven.
And then, to my surprise, she invited us to join them.
We couldn’t make it work logistically—but something had been set in motion.
When One Idea Opens Another
At the same time, John and one of his closest friends from business school were reminiscing about their past hikes through the Wind River wilderness in Wyoming. No internet. Tents. Bear spray. Freeze-dried meals. Blissfully rugged.
But this year, wildfire risks and air quality concerns were making another trip feel too uncertain.
So, the conversation turned toward Europe—somewhere we could walk, unplug, and reconnect with nature in a way that was physically immersive but logistically smoother. As it turned out, the other couple had travel plans to Sicily in June, which opened up an opportunity for us to join forces for a new kind of adventure.
John had long been curious about the Via Francigena, an ancient pilgrimage route that winds through Italy—including the Tuscan countryside. But as we researched, we realized many sections involved walking along roads—often with traffic. That wasn’t the experience we were craving.
Enter: Val d’Orcia
I mentioned our evolving plans to an old architect friend who is a Tuscan and knows Tuscany intimately.
His response, via WhatsApp voice message, was simple and decisive:
“If you come all the way to Tuscany and want to walk town to town and really experience what you’re describing… why not explore Val d’Orcia?”
That was it. We pivoted.
And with that, the plan unfolded.
Our Itinerary: Hiking Through the Heart of Tuscany
We decided on a six-day walking route through five towns:
Buonconvento (starting point)
San Quirico d’Orcia
Pienza
Montepulciano
Montalcino
Then we’d spend four nights in a modest villa in Monticchiello to rest, restore, and savor the afterglow of the experience.
This wasn’t going to be a rugged, backcountry backpacking trip. We wanted long walks by day and good wine by night—well-appointed hotels, nourishing meals, and time to reflect and connect.
We arrived in each town by mid-afternoon, giving us plenty of time to refresh, wander the streets of hilltop towns, and scout out a great spot for dinner.
We booked the hotels, reserved the villa, and started training.
What the Trail Taught Me—And How You Can Use It
Our week in Val d’Orcia wasn’t just a vacation; it was a living laboratory for the very principles I coach my clients through every day. Five themes kept showing up on the path. See which one speaks to you right now:
🌱 1. Vision Begins With Self-Connection
It wasn’t a grand blueprint that set this trip in motion. It was the quiet yes I felt when my friend spoke about her Tuscan ritual—and my decision to honor that whisper instead of brushing it off. Curiosity did the rest, and a life-giving adventure unfolded.
Try this: When a flicker of excitement, envy, or longing appears, pause. Ask, “What is this feeling showing me about what I truly want?” Give it one small “yes” this week.
🌿 2. Flexibility Protects Your Energy (and Your Joy)
Maps changed. My feet blistered. One leg of the route became a 30-minute bus ride instead of a six-hour hike—and that pivot let me savor the journey and stay present with my friends. Adaptability wasn’t failure; it was wisdom in motion.
Try this: Where are you forcing yourself to push through? What supportive detour—or dose of help—would let you keep moving without burning out?
🧩 3. Systems Make Space for What Matters
Suitcases safely stored in Buonconvento, morning pack-and-stretch rituals, snacks stashed in the same pocket every day—tiny systems that freed our minds to enjoy the walk. Yet I still overpacked, and the extra weight showed me how unseen burdens can pull us off course.
Try this: Name one physical or mental load you could set down. What simple system would keep life lighter so you can stay on your path?
🚶♀️ 4. Alignment Lives in Each Step
Progress wasn’t about perfect conditions; it was the daily choice to lace up and take the next step—sore muscles, uncertain weather, and all. Tiny, consistent actions turned intention into reality.
Try this: Identify one decision you’ve been postponing. Commit to a single, doable step today that moves you closer to the life you want.
🧘 5. Rest Isn’t a Reward—It’s Part of the Rhythm
Every day asked something of us, but built-in joys—long lunches, early arrivals, golden-hour wandering—kept effort and ease in balance. Our four villa nights deepened that rest: space to integrate, reflect, and let the experience land.
Try this: Schedule your next pocket of rest before exhaustion demands it. Let renewal be a rhythm, not a rescue mission.
Bringing It Home
Hiking Tuscany taught me what I invite my clients to practice year-round: listen within, pivot when needed, lighten your load, act in alignment, and weave rest into your life—not as a finish line, but as part of the pattern.
✨ You don’t need to hike through Italy to reconnect with yourself. You just need space, intention, and support.
📥 Grab my free guide “Energy Budget Starter Kit” to begin right now
