Discover the Charms of a Forgotten Tuscan Hamlet


Check in to an Italian retreat perched on a hill midway between Rome and Florence and discover the charms of a forgotten hamlet with sweeping valleys, terracotta roofs and winding roads.

Our rental car’s GPS tells us we’re close to the tiny Tuscan village of Castiglioncello del Trinoro, except it fails to consider that there’s a field and a mountain in the way. Castiglioncello means “little castle” and it sits high above the UNESCO World Heritage-listed Val d’Orcia, one of Italy’s most serene valleys. We can see the terracotta roofs of houses from where we’ve come to a halt in the rutted field but they’re frustratingly out of reach. When we eventually kill the GPS and follow our instincts, Tuscany’s famous white roads lead us quickly to the town gates.

Castiglioncello del Trinoro is worth the convoluted journey. Its secluded location and sublime views are two features that drew Cincinnati-based corporate lawyer and law professor Michael Cioffi here more than a decade ago. He was holidaying at a nearby villa when he “fell in love at first sight” with the forgotten hamlet, halfway between Rome and Florence, which had been a rest stop on the pilgrim route from Rome to Canterbury in medieval times. “It had retained its medieval character with almost no interference from the outside,” he says. “So there was this sense of being lost in time.”

When several houses in the 900-year-old town became available for sale, Cioffi purchased them and enlisted the help of Rome-based architects Ilaria and Giorgio Miani to rebuild and reinvent the interiors, which had mostly fallen into ruin. He gave the collection of rental villas a name, Monteverdi, for his mother’s family, for the composer whose work he admired and for the green hills that surround it.

The local residents, whose families had lived there for generations, were wary of the foreigner buying up their sleepy village, fearing their summers would be overrun by noisy interlopers. But Cioffi’s intentions for Monteverdi were sensitive to those concerns, inspired by the idea of albergo diffuso, where failing villages are revitalised when a few houses are turned into tourist accommodation, embedding travellers in village life. 

Cioffi hoped to take this model further, not only creating beautiful spaces to rent but also sponsoring events in art, literature, music and gastronomy, making Monteverdia centre where the arts and humanities would flourish. “Michael wanted to create a cultural, emotional experience,” says Ilaria Miani. “He really is like a Renaissance prince.”

What he didn’t want to create was a theme park but Monteverdi feels far from that. It’s still a place where a small number of people live year-round, even through the snowy winters (Monteverdi is closed from mid-November to March). Wherever possible, Cioffi and his team have tried to maintain the authenticity of the setting and the medieval character of the buildings. The task was massive. Miani combed Italy for architectural details, such as ancient beams and handcrafted tiles, to replace poor contemporary materials used in previous renovations. The architect says it was all carried out “with no restraint on expenses”. 

One expense not anticipated was “the dig”. Early on in the restoration, builders uncovered artefacts on the property from the original Etruscan settlement and the foundations of a castle dating back to 1127. Despite the massive cost of uncovering and preserving the ruins for posterity, Cioffi was determined to reconnect the village with its past. It’s the only privately funded archaeological dig in Tuscany, overseen by a professor from the University of Siena. 

Monteverdi has grown organically over several years, a glorious project involving the sort of care – and injections of cash – that might leave less passionate investors shaking their heads. The modest village, which lost many of its citizens to Italy’s urban centres after World War II, has been re-energised. The Monteverdi project now includes an art gallery and artist-in-residence program with a first-class curator, Sarah McCrory, in charge; a 14th-century church that’s been retrofitted to become a music venue and an outdoor stage; as well as a lively enoteca and a restaurant serving seasonal, sustainable Tuscan food.

Then there are the three luxury villas and a 12-room hotel occupying a row of townhouses. Gardens have been landscaped, a swimming pool has been added and a spa opened last year, using products sourced from a centuries-old Tuscan farmacia and offering Etruscan-inspired bathing rituals with views of the valley.

The quiet road leads us to Monteverdi when the town is in full bloom: rambling roses and honeysuckle tangle over the stone walls; lavender and rosemary hedge the paths; and the houses, with brightly painted doors that open directly onto the street, are decorated with dazzling pots of hydrangeas. The village’s main street is so narrow that our car almost touches the walls of the houses on either side. There are startling views of the valley with avenues of cypress trees at almost every turn. As tranquil as the setting is, the village is nevertheless bustling with tradesmen working on a villa conversion, cyclists and motorists passing through, locals chatting in doorways and hotel guests sipping coffee on the many terraces. 

The villas, which are rented by the week, are scattered throughout the village. The largest, three-storey Villa Muri Antichi, has six bedrooms. At one time, at least 20 people and their animals lived in each of these peasants’ houses. Hotel Monteverdi, created for shorter stays, occupies a former pensione. We’re sleeping in room No. 5, or “the green room”, named for its pastel-washed timber. It’s charmingly rustic, with heavy ceiling beams. Linen bedding and furnishings have been sourced from local carpenters and tradesmen. All rooms are individually decorated – No. 6 next door has an extravagant freestanding copper bathtub.

Monteverdi creates a problem for us: we’re keen to enjoy the village and all that it offers but we’re also eager to drive down into the valley and cut a swathe through the vintages of Montepulciano, Chianti and Brunello. There’s no shortage of advice on where to go, as bon vivant Cioffi is keen to promote local winemakers and provedores. Then again, the enoteca dispenses 32 wines by the glass and the views from Monteverdi’s terraces are magnificent. It’s very tempting just to be in this transcendent space.

There are a number of annual events at Monteverdi, apart from the ongoing arts programs, that provide further reasons to spend time in the village. Cioffi is the sponsor of the eight-day music festival Incontri in Terra di Siena, held each July in the famous gardens of neighbouring La Foce estate. Monteverdi sponsors and hosts selected events at the annual Sarteano Jazz & Blues festival and British maestro Sir John Eliot Gardiner holds a one-week boot camp for aspiring singers each April. Every Wednesday in summer, musical events take place in the piazza.

Ilaria Miani says it’s important for guests to understand that Monteverdi “is not a resort”. It’s part of a community, she says, with “an incredible exchange of energy”. Cioffi also hosts scholars, exchange students and summer interns from Cornell University’s hospitality program in the United States. On any sunny morning, Monteverdi may look sleepy but it’s buzzing with creativity.

As for its benevolent creator, he hopes guests will appreciate “the life of the mind” and visit the village to “think and talk and have great food and drink great wine”. Just taking in the view is fine, too. 

Classic Tuscany

Monteverdi is the perfect base from which to tour the heritage-listed Val d’Orcia region. Here’s what to do...

Visit a historic villa

The 15th-century La Foce was inherited by Benedetta Origo Isidori, daughter of Anglo-Irish writer Iris Origo and nobleman Antonio Origo, who were responsible for great agricultural and social improvements in the impoverished valley from the 1920s. The formal gardens, which are open to the public on certain days, are considered the finest example of the work of British architect Cecil Pinsent. Dopolavoro, a nearby café, was once the after-work social club for the estate’s workers.

Eat with la famiglia

Podere Il Casale is a picturesque lunch spot between Pienza and Montepulciano, which includes a biodynamic farm, a cheese factory and a rustic restaurant with spectacular views of the surrounding countryside. Tuscan cheesemaker Ulisse will take you on a tour of the factory if you reserve ahead. His wife, Sandra, cooks hearty organic meals in the very family-friendly restaurant. Children will be happily distracted petting the animals.

Explore vineyards

The Val d’Orcia is famous for its fine wines, especially the Brunello di Montalcino, made exclusively from sangiovese grapes. The towns of Montalcino, Montepulciano and Pienza are surrounded by vineyards. A number of wineries open their cellar doors, such as the impressive winery at Rosewood Castiglion del Bosco, an estate established by the Ferragamo family. It hosts tasting seminars year-round and a harvest event in September.

Seek wellness

Fans of Federico Fellini will enjoy a visit to the thermal springs in the municipality of Siena, where the Italian director shot his masterpiece, 8½. The Etruscans built a temple here in the fifth century and some Renaissance architecture survives. The modern Terme di Chianciano is one of the finest health resorts in Italy, with hotels, springs, thermal baths and lush parklands.


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