On a sun-drenched April afternoon in the hilltop town of Cortona, my husband, David, and I are sitting, pistachio gelato in hand, on a wooden bench just off the piazza that Dutch violinist André Rieu dubbed Italy’s most romantic square.
We’re overlooking the 13th-century town hall, which evokes a castle with its balcony and bell tower. From the grand stone staircase of Piazza della Repubblica, generations of newlyweds have started lives, descending into the heart of this ancient walled city.
“This is what it’s all about,†David says as we watch the scene unfold. His words settle something inside me. We’re in Italy on a whirlwind trip to mark our 25th wedding anniversary, and for once, I have no itinerary. It’s thrilling.

The writer and her husband on their wedding day, 25 years ago.
Shelley Cameron-McCarronThe approach of our milestone anniversary was a keen reminder that time prioritizes no one — but I should. Especially this relationship, which has given life such shape.
The mindset shift made me, usually the perfectionist planner, take stock. Could we show up in Tuscany and Rome and wing it? Hardly. But orchestrating everything and trying to do it all? Exhausting. So I surprised myself and my easygoing husband by sketching out the most bare-bones plan, with only glancing nods to some must-sees, and many days left wide open.
Our skimpy planning allows for serendipity. That’s how we find ourselves stopping to explore when a town, thermal spring or enchanting view catches our whim, slowing down as we zip through Val d’Orcia in a rental car. Filled with fields, farmhouses and stands of cypress trees, the Tuscan countryside is so idyllic that the movie “Gladiator†used it to portray heaven: General Maximus’s Spanish home.

The beautiful countryside of Val d’Orcia, in southern Tuscany.
Gehringj/iStockIn Cinque Terre, in Italy’s northwest, it’s raining steadily as our ferry docks in Vernazza, the fourth of five centuries-old fishing villages located, improbably, in the cliffs. The downpour splashes over café umbrellas, deserted patios and gozzo boats. The weather may not be perfect, but I’m still smiling. I beam at David. Come what may, we’re in this together.
We grab hands, spurred by playful spontaneity, and dash for refuge inside a 13th-century Catholic church, Santa Margherita d’Antiochia, rising at Vernazza’s edge. Candlelight flickers on weathered walls, the darkened stone interior redolent of the Ligurian Sea.
In glorious Florence, the city’s beauty astounds us in the open-air statues, in squares and museums, and at Ponte Vecchio, the bridge spanning the Arno River. But David and I don’t need monumental sights to be happy. Our favourite memories on this trip are of lingering in trattorias, getting lost, and eating decadent cake — lemon, chocolate, hazelnut — at hotel breakfasts (it’s an Italian thing!).
I sometimes forget we’ve abandoned an itinerary. Our days feel full, even if we’re just relaxing on a marble ledge in a town square or chatting with a friendly shopkeeper. It’s more than OK to be here doing “nothing†together.
Away from home, we’re reminded of who we are at our core, beyond the busy working parents who’ve raised three kids. We’re still the people we once were. And also the people we’ve become. In the last quarter-century, there have been babies born, a house bought, a mortgage paid off, a blur of swim lessons, graduations and greying temples that suddenly put us on the other side of 50. Not young, but young at heart.Â

Left: Shelley Cameron-McCarron and her husband, David, in Cinque Terre. Right: The writer taking in Rome’s Colosseum.
Shelley Cameron-McCarronAs we travel from the Sistine Chapel to Siena’s shell-shaped main square, where bareback jockeys famously dash for glory, I feel we’re chasing ghosts, flashes of our former selves. I remember us as hopeful newlyweds, giddy with excitement, with little cash but huge chutzpah fuelling our dreams.
In Montepulciano, Tuscany, we stay at Borgo San Vincenzo, a historic farmstead turned boutique hotel set among the vineyards. One night, over hand-rolled pici al ragu in the outdoor pergola, in the soft glow of the sinking sun, I feel both present and lost in yesteryear. We’re not just celebrating 25 years but all the moments in between.
“What’s been your favourite experience?†I ask. David’s answer echoes mine. “Time with you.â€
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