Checking-in to: Castiglion del Bosco, A Rosewood Hotel

CHECKING-IN TO | CABANA TRAVEL | WORLD OF CABANA

Villa Santa Anna claimed Erica Firpo from the moment she walked inside and sat down on the salotto’s soft leather couches. The beautiful private house is one of 11 properties (and 42 suites) on the 2000-hectare Tuscan estate managed by Castiglion del Bosco, A Rosewood Hotel. The medieval village-hotel was once owned by the Ferragamo family who began a sensitive restoration and remain deeply involved in the ever-evolving estate.  

BY ERICA FIRPO | CABANA TRAVEL | 12 FEBRUARY 2026

A villa bedroom at Castiglion del Bosco, A Rosewood Hotel © Davide Lovatti.

Some landscapes seem to resist comparison, and the Val d’Orcia is one of them. Here, the colors seem richer, more saturated, the scent more pronounced, and the falling light more deliberate. Even the fog, which curls gently through vineyards at almost every dawn, possesses a beauty so refined it seems curated. This is Tuscany at its most persuasive, needing neither explanation nor embellishment.

Staying at Castiglion del Bosco, A Rosewood Hotel means entering this heightened version of the countryside. After traversing the rolling hills near Montalcino, a UNESCO World Heritage landscape, the road turns gravely, the woods grow denser, and everything quiets. Deer linger at the forest’s edge. The air carries the scent of damp earth, woodsmoke, and wild herbs. Arriving in the medieval hamlet – where Rosewood is now bedded in – feels less like check-in and more like a homecoming. 

The country style kitchen at Castiglion del Bosco's Villa Santa Anna © Davide Lovatti.

Massimo and Chiara Ferragamo felt much the same when they first encountered the village in the 1990s. By then, most of its inhabitants had drifted away to nearby Buonconvento or Siena, leaving behind a place once sustained by tenant farming and daily labor. Nearly 900-years-old, the former stronghold had become a quiet assemblage of stone stables, workshops, and row houses gathered beneath an ancient tower. What the Ferragamos recognized was not decay, but a rare continuity of land and culture.

Purchased in 2003 with the modest intention of creating a private retreat for family and friends, the estate soon revealed a larger calling – a village ready, once again, to live. The medieval borgo was sensitively converted into rooms and suites, while freestanding villas were restored from abandoned farmhouses across the estate’s 2,000 hectares.

Chiara Ferragamo shaped the villa's interiors with country elegance © Davide Lovatti.

Today, Castiglion del Bosco offers 42 suites (23 woven into the fabric of the historic borgo and 19 on the hillside above) alongside 11 private villas across the surrounding landscape. Chiara Ferragamo shaped the interiors with a Tuscan country elegance: wooden furniture, neutral linens, cashmere throws, and carefully chosen antiques. 

In 2015, Rosewood took over hospitality management and, in 2022, the Ferragamos sold the property itself to an international group, but remain closely involved in the project to which they are visibly and personally attached. The estate’s scale allows it to function as a world unto itself. Dining ranges from the Michelin-starred Campo del Drago to the deeply Tuscan Osteria La Canonica, both guided by executive chef Matteo Temperini, while a Tom Weiskopf–designed private golf course, often cited as one of the most beautiful in Italy, unfolds across vineyards and woodland.

A picturesque ruin in the grounds of Castiglion del Bosco © Davide Lovatti.

Staying at Villa Santa Anna was a pleasure – the house had claimed me from the moment I walked inside and sat down on the salotto’s soft leather couches. Exposed stone walls, warm woods, soft linens, infinity pools, cabanas, and an uninterrupted 360-degree view of the valley – it felt like home, as if I were a secret Ferragamo child. It helped that there was a full-time mamma in villa moving through the villa all day, a Castiglion del Bosco touch that aims to provide whatever comfort the day requires.

A Land Rover Defender stood ready for exploring the estate’s farthest reaches, though the greater pleasure lay in staying put: reading by the fireplace, watching the light shift across vineyards and woodland, allowing time to stretch. Luxury, here, was the freedom to linger. One morning unfolded as a truffle walk with a local forager and his young Lagotto Romagnolo. Walking the land proved the real indulgence—rolling hills, vineyards, olive groves, and dense forest, uninterrupted and quietly alive.

Castiglion del Bosco, a Rosewood hotel, has 11 private villas © Davide Lovatti.

When the hunt ended, truffles in hand, I walked back uphill into the medieval borgo, then continued on to La Canonica for lunch. The freestanding stone villa is, by all accounts, Massimo Ferragamo’s favorite place on the estate, and it's easy to see why. Its views over the Val d’Orcia are so hypnotic they threaten to derail any plan entirely.

A cooking lesson proved irresistible too: comfort rather than cliché. Making a cheese-and-truffle pasta felt light-years removed from the usual performative pizza or ravioli rituals. Brunello from Castiglion del Bosco flowed easily, alongside a particular spumante from Fèlsina, the Siena-area organic wine pioneer.

A cozy ground floor bedroom at Villa Santa Anna © Davide Lovatti.

Evenings can be as cozy and casual as homemade pizza back at the villa, or as memorable as dinner in the wine cellar, home to the exclusive 1100 Wine Club. The cellar is a circular stone rotunda lined with 174 individual wine lockers, where members store prized Brunello and other bottles introduced through Ferragamo’s own network and taste. If Albus Dumbledore had designed a wine cave, it might look something like this – serious, faintly magical, and deeply reverent.

It comes as no surprise that Castiglion del Bosco has so rightfully been awarded three Michelin Keys, and what distinguishes it is not spectacle but integrity. The borgo is preserved rather than embellished, resisting the temptation to Disney-fy the Tuscan experience. Quality reveals itself constantly, but not loudly: it's in the gentle pacing of days, the tactility of materials, the impeccable standards of hospitality and craftsmanship, and the small personal gestures – an embroidered napkin at first breakfast, embossed leather luggage tags waiting discreetly in the room, a walk in the forest and pots of tea and homemade cakes awaiting you on return. 

Castiglion del Bosco, a Rosewood hotel in Tuscany © Davide Lovatti.