I’m a Food Writer—and I Discovered the Most Luxurious Way to Eat Through Tuscany

I’ve always loved to walk. I’ve lived in walkable cities and built a lot of my personality on schlepping around town—sometimes while carrying my body weight in groceries. When we moved to a small town in New Jersey, I kept walking on the Delaware and Raritan Canal State Park Trail, first with a baby strapped to my chest, then pushing a double stroller, often with our dog, Ace, in tow.

So when the chance came to explore Tuscany—one of my favorite places in the world—on a hiking and biking trip with Butterfield & Robinson, it was an easy yes. The luxury active-travel company, celebrating its 60th birthday this year, made everything feel elevated and seamless, yet still deeply personal. Even a jaded food and travel writer like me felt exquisitely taken care of.

Some touches bordered on magic: prosecco and ricciarelli—those soft-centered Tuscan almond cookies with a crisp shell—waiting at intervals along the trail; luggage that somehow migrated from one boutique inn to the next, always in my room before I arrived. “Our trips are often compared to theatrical productions,” explained Courtney Mundy, a Butterfield & Robinson experience designer based in Florence. “We do our best planning and rehearsing behind the scenes so the only surprises along the way are wonderful.”

Butterfield & Robinson’s philosophy is simple: Slow down to see the world. “By slowing down and taking in a region one step or cycle at a time, our brains and bodies are forced to breathe more deeply, pass through the world more slowly, and therefore absorb more of our environment,” Mundy said.

That idea came alive on my favorite day of hiking, ascending through the Val di Chiana—a valley carpeted in red poppies, sunflowers, and sweetgrass—toward the 13th-century hermitage of Celle di San Francesco, where St. Francis is said to have written his last will and testament. I stopped for a moment of quiet in the sunshine before continuing up through olive groves toward Cortona. Lunch at La Loggetta tasted even better for the climb: silky pappardelle with wild-boar ragù and nutty sheep’s milk cheese, the pasta made from Verna wheat grown in the very fields we’d been walking through.

The wheat fields themselves told their own story—deep brown and newly tilled in autumn, then green in spring, golden in summer. Mundy put it beautifully: “Exploring any spot by bike or foot allows people’s perspectives to widen. You feel a deeper connection to a place, you move at an intentional pace, and you use all your senses. You hear the birds, smell the rosemary, and receive a cheerful ‘Buongiorno!’ from a local.”

The Ride (and the Fall)

If walking was bliss, biking was… humbling. The sleek e-bikes were smooth, but I’m a novice cyclist and a bit of a scaredy-cat. The narrow Tuscan roads, steep curves, and zippy Italian drivers triggered a full fight-or-flight response. I took one corner too sharply and met an ancient stone wall—scraped knees, bruised pride, no lasting harm. Still, it confirmed what I already suspected: Biking isn’t for me. Walking is.

Yet biking delivered me to one of the trip’s most transcendent spots: Ultima Pietra, an estate that seems to float above vineyards and olive groves near Trequanda. Proprietor Margot Stone Bowen told me, “Driving through the Val d’Orcia, your heart skips a beat with every turn. But to bike or hike these same ancient paths allows time to slow to a near standstill.”

At Ultima Pietra, blossoms of jasmine and lavender perfumed the air; rosemary cascaded down stone walls; and butterflies flitted through the vines. “At this slower pace, Tuscany begins to reveal its true, complicated, and extraordinary self,” Bowen said.

Over lunch, we tasted her estate’s peppery new olive oil (harvested barely a week ago) and vibrant Merito merlot while gazing across the UNESCO-protected hills. Bowen explained the vineyard sits “at 500 meters above sea level, among the highest Tuscan vineyards,” its altitude lending freshness and minerality. It felt like a metaphor for the entire journey: finding a new perspective by slowing down and climbing up.

The Art of Care

Every evening, there was another feast: pici pasta we rolled ourselves in a candle-lit trattoria in Monticchiello, or a meal in a private villa where local chefs poured Chianti and stories in equal measure. These moments—half activity and half ritual—blurred the line between traveler and local.

Mundy called this approach “a misura d’uomo”—human-sized travel. “Walking and cycling put us back into our human dimension,” she said. “In a land and culture shaped by agriculture, that fosters an inevitable connection with locals and the traditions born here.”

It’s easy to romanticize Tuscany—the cypress-lined roads, the terra-cotta rooftops, the infinity pools perched over the vineyards—but this trip transformed that postcard beauty into something tangible. I felt it in my feet, in the sweat on my back, and in the first sip of wine after a long climb.

Time is the greatest luxury of all. This trip gave me permission to spend it lavishly: walking through poppy fields, talking with winemakers, and slowing down enough to taste the land itself.

Where to Stay

Casa Newton, Pienza

Tucked in the rolling hills outside Pienza, Casa Newton feels like a modern dream of the Tuscan countryside. Its 11 guest rooms and suites blend contemporary design with local craftsmanship—sleek lines softened by handwoven linens, reclaimed wood, and terra-cotta floors. I loved the sense of play in the decor; everywhere I looked was a postcard-perfect tableau, from the sculptural chairs to the way morning light hit the infinity pool. Between the cozy sitting areas and the spacious Italian gardens, it’s the kind of place that invites you to exhale, linger over an espresso, and watch the rhythm of rural life unfold.

Villa di Piazzano, Cortona

Once the 16th-century hunting lodge of a Tuscan cardinal, Villa di Piazzano has been lovingly restored into an elegant country retreat overlooking olive groves and wheat fields. When we arrived, the Italian-Australian owners welcomed us like old friends. I sipped an aperitivo in the garden as the sun melted behind the hills, the perfect end to a long day’s walk. The villa balances history and ease—vaulted ceilings, frescoes, and antique touches, paired with the kind of warmth that makes you feel instantly at home.