POSTCARD FROM TUSCANY
There’s a certain magic to the Italian countryside: a slower heartbeat, a richness that reveals itself in layers, like a Barolo opening in the glass. Time is kept not by clocks but by the rhythm of long lunches, the shifting light across the hills, and the distant toll of church bells. Life is unapologetically about beauty—the golden haze over olive groves, the scent of wood-fired bread from centuries-old kitchens, the hum of cicadas in the midday sun.
Traveling here isn’t about landmarks; it’s about surrendering to the cadence of the land, letting winding roads lead you to hilltop towns, hidden trattorias, and conversations with locals who carry the history of this place in their voices.
OUR JOURNEY THROUGH
THE ITALIAN COUNTRYSIDE
TUSCANY
Borgo Pignano
Our journey began in Pisa, where rolling vineyards spill toward the horizon and stone villages perch like quiet sentinels over the hills. From there, we meandered south into the heart of Tuscany—the land of cypress-lined roads and golden villas. Our first stop was Borgo Pignano, a beautifully restored 18th-century estate that feels part artful retreat, part working farm. We stayed in the Suite San Bartolomeo in La Canonica—a spacious two-bedroom apartment whose sweeping views made lingering over morning coffee irresistible. Inside, elegance met warmth in perfect balance: stone walls with refurbished hand-painted drawings and antique beams softened by light-filled rooms and thoughtful pops of color. And the ultimate bathtub to overlook it all.
Evenings unfolded with aperitivo in the courtyard as the sun melted into the hills; mornings began to the chorus of birdsong as we painstakingly debated what to try from the generous breakfast spread. Borgo Pignano is the kind of place you settle into, not just pass through—a dream base for a countryside wedding or an escape with family and friends. With activities from beekeeping to soap-making, it’s a haven for embracing slow living at its most refined.
Siena
From there, we spent a day in Siena—an ochre-hued jewel tucked into the Tuscan hills, and a place one of my most well-traveled friends swears is his favorite. We arrived just before the build-up to the famed Palio di Siena, the centuries-old bareback horse race that transforms the city into a stage for neighborhood pride and rivalry. Each contrada, or district, pours its soul into the festivities, lining the medieval streets with colorful flags, hosting communal dinners under the stars, and filling the air with chants, drums, and song. Even outside of the Palio, Siena radiates a timeless charm, from the striped marble Duomo to tucked-away cafés and artisanal shops. The city feels like a living museum—intimate, enchanting, and impossible not to fall in love with.
Monteverdi
We then headed deep into the mountains of Tuscany to Monteverdi. Getting there was half the adventure—no Google Maps pin, just hand-written directions that led us down winding lanes and a long dirt road. But as soon as we arrived, it was clear it was worth every turn.
Monteverdi isn’t just a hotel—it’s a whole village, lovingly restored and overlooking the Val d’Orcia. Think cobbled medieval streets lined with contemporary art galleries, an ancient stone church, and courtyards filled with wildflowers swaying in the breeze. Every detail felt intentional, from the in-house florist who fills the rooms with whimsical arrangements to the serene pool that seemed to dissolve into the Tuscan hills.
The interiors struck that rare balance of old-world soul and modern design. Our room was washed in a cheerful turquoise, warmed with wood beams and antique touches, yet layered with contemporary artwork and sleek textiles. The bed—massive, cloudlike, and piled high with linens—was impossible to leave. Each window framed the hills as though they were living paintings.
And then there was the spa—an immersive sanctuary carved into stone, with thermal baths, hammam rituals, and treatments that blended modern skincare with centuries-old traditions. Time seemed to slow here, as if Monteverdi had its own rhythm.
The food and wine only heightened the magic. We began with cocktails on the veranda as the sun spilled across the hills, then moved to their hillside trattoria, where rustic Tuscan flavors were reimagined with refinement and paired with a thoughtful selection of local wines. Each glass felt like a tribute to the land itself.
From start to finish, Monteverdi was less a stay than a love affair—an experience that lingers long after you leave. I don’t say this often, but it has earned a place among my absolute favorites.
UMBRIA
Reschio
Tucked between Tuscany and Le Marche, Umbria is often called Italy’s “green heart”—a land of misty valleys, medieval hill towns, and rolling vineyards that feel untouched by time. Unlike its more famous neighbor, Umbria is quieter, wilder, and deeply soulful; a place where daily life still moves to the rhythms of the land. It’s here, amid this serene backdrop, that you’ll find Reschio, a castle estate that captures everything magical about Umbria while elevating it into an art form.
Reschio doesn’t feel like a hotel; it feels like a home you dream of owning. Every detail has been thought through with precision and warmth, creating a world that is about pure intentionality. From a whimsical welcome drink served among flowers and riding boots to staff in custom Italian uniforms, every gesture felt considered.
Days unfold with yoga overlooking the hills, horseback rides from world-class stables, or time at the pool framed by cypress trees. Evenings brought cocktails crafted with their own gin and amaro, and dinners split between a rustic trattoria with valley views and a refined castle restaurant.
And then, the music. Each night, the Palm Court—a glasshouse at the heart of the castle—fills with the sounds of a Steinway piano, often played by guests themselves. It’s a cinematic moment: a negroni in hand, candlelight flickering, piano echoing under glass.
Even the rooms carry that thoughtfulness—private bars stocked with house-made spirits, bespoke slippers, custom toiletries, and small, unexpected gifts. For those who can’t bear to leave, Reschio offers restored farmhouses to purchase, weaving guests into the estate’s legacy.
Reschio isn’t just a stay; it’s an invitation into a way of life.
HONORABLE ACCOLADES
Not everything fit neatly into our itinerary—but some places and brands deserve a spotlight all their own.
These are the names and spaces I’ll return to, shop from again, or dream about until I’m back in the Italian countryside.
A 16th-century palazzo in the heart of Rome, once home to Angelo Maria Colocci and later the city’s oldest school. Restored by the Federici family with design by Luca Guadagnino’s studio, it blends Baroque grandeur with cinematic Italian style. Food leaned too ambitious, but cocktails were exceptional, and the property itself offered a calm, design-driven refuge from the city’s intensity.
In the heart of Sicily, a lovingly restored family estate showcasing the island’s bounty of wines, cheeses, and produce. Rain accompanied much of our stay, but the food and beverage program shone—especially the breakfasts of fresh juice, Sicilian specialties, and farm-fresh dairy.
A 17th-century castle on the Tyrrhenian Sea, once the villa of J. Paul Getty and filled with Renaissance treasures. A touch lacking in soul compared to other stays, but its branding details—from dishware to apparel—were beautifully executed.
A neighborhood gem just beyond Rome’s center, celebrating cucina romana with precision and heart. The amatriciana was unforgettable, paired with a thoughtful natural wine list of small producers.
Rome’s finest hat atelier, blending tradition and artistry into sculptural designs perfect for both style and function.
A Roman tailoring institution, where generations of artisans craft bespoke suits from the finest fabrics. Be prepared to wait—orders can take six months or more.
A small family-run winery that feels unforgettable thanks to Mau, the larger-than-life host who brings humor, tradition, and warmth to every tasting. The experience is intimate and deeply rooted in local heritage, making it feel all the more special.
Set high on a volcanic cliff, Orvieto is a small Umbrian town with real charm. Its Gothic Duomo is the star, with an intricate façade that’s worth the trip alone. The town itself is easy to enjoy on foot—narrow streets lined with artisan shops, local trattorias, and plenty of chances to try the region’s crisp Orvieto Classico wine. Simple, walkable, and full of character, it’s an ideal stop between Tuscany and Umbria.
READY TO PLAN YOUR ESCAPE?
Your Italian countryside journey is waiting.
If this sounds like the Italy you’ve been dreaming of — slow mornings, hidden towns, and hotels that feel like home — reach out, and let’s craft a journey that’s entirely yours.
Let us craft a journey with soul, stillness, and a little sparkle.
