Having spent most of the last millennium as a fortified village, Castiglioncello del Trinoro was largely abandoned in the 20^th century—then reimagined three years into the 21^st, when a visiting Ohioan fell hard for this hilltop beauty. “Walls were collapsed, roads washed out, roofs caved in and gardens overgrown,” says Michael Cioffi—the Cincinnati lawyer in question—of his then new love. “I became obsessed with protecting and preserving her.” So he enlisted the help of an equally besotted designer, the Rome-based Ilaria Miani, and set about creating one of the best hotels in Tuscany: Monteverdi. 

Named for the composer Claudio Monteverdi—an icon of the Italian Renaissance and a favorite of Cioffi’s—the project represented a different kind of rebirth. Tucked away in the UNESCO-listed Val d’Orcia, derelict stables and farmhouses became meticulously appointed guestrooms and villas. A medieval church and its adjoining piazza became a concert and cultural event space. And the village schoolhouse became a state-of-the-art culinary academy. 

The resident spa has long been part of the appeal, not least because of a water circuit that blends hillside and subterranean soaking spots of varying temperatures—and invariably stunning surroundings. But this year’s addition of a cutting-edge wellness center puts Monteverdi squarely on the retreat map. With Dr. Maurizio Cavallini as chief medical advisor and a Doctor in Residence series that will bring in specialists from across Italy, the lineup focuses on minimally invasive, science-driven treatments: biological age and oxidative stress testing, cryotherapy, laser resurfacing, radiofrequency therapy and IV therapy, to name a few. 

You’ll also find new wellness packages, from the year-round, three-day Tuscan Tranquility Retreat to next month’s Holistic Detox Retreat (November 12-19). But whether or not you’re an official participant, the spirit of retreat is hard to beat here. Hence the long line of creatives who’ve done residencies at Monteverdi, like this year’s Yale Drama Series Prize finalists. 

“There is a special place at Monteverdi for the arts and humanities,” explains Cioffi. “As part of our Artist and Scholars in Residence program we invite an eclectic group of leading contemporary painters, sculptors, scholars, singers and musicians to exhibit at the Monteverdi Art Gallery, to lecture and hold concerts.” 

On the other hand, if your idea of retreat involves solitary contemplation, countless walking trails await—and they’re particularly inviting in late October and early November, when the air is getting crisp, the hills are turning ochre, the grapevines are deepening into oranges and reds, and a golden mist is, on especially good days, hovering over everything. Note that if you’d like to add some yoga, meditation and forest bathing into your walks, Monteverdi’s specialist can accompany you to the nearby Pietraporciana Nature Reserve, where your asanas will be set against a fiery beechwood backdrop. 

Refueling between your wanderings is equally sublime this time of year, when local truffles, porcini and chestnuts abound, and Culinary Director Giancarla Bodoni dives deep into the seasonal bounty. But some would argue that the most delicious experience to be had at Monteverdi is a seat on the terrace—a latte macchiato (or hot spiced wine) in hand, and the hills of the Val d’Orcia undulating below. monteverdituscany.com