Picture a Tuscan landscape and what do you see? If it’s a chalky white track dotted with feather-shaped cypress trees zigzagging up a hill, then congratulations, you have transported yourself to the Val d’Orcia. This staggeringly beautiful area of vast open hillsides is located in deepest southeastern Tuscany, between Siena and the Umbrian border. This is where postcard-makers come to photograph the rolling mists at dawn. It’s probably already on your screensaver.
Tuscany’s popularity with the Inglesi is so notorious that at one point it was labelled Chiantishire, an extension of the home counties. But this is not Chi- anti, those tight-knit hills just south of Florence. The Val d’Orcia is far from any airport and the landscape is wilder, less populated. The farmhouses that crown each hill are more likely to be roofless than to have a pool. Until recently it was very poor.
The person who did most to put the Val d’Orcia on the map was herself half-English. Iris Origo, granddaughter of Lord Desart, wrote one of the great wartime diaries, War in Val d’Orcia, which captures the quotidian fears and deprivations of life in the early 1940s. The book tells how Origo’s home, La Foce, a one-time coaching inn on a crossroads, became a refuge for the displaced — partisans, deserters, escaped prisoners and orphans. In a moving climactic scene, as the Allies push north through Tuscany, Origo leads 32 children on foot to the safety of Montepulciano. “Are the Germans really coming to eat us up?” asks one.
Today the effects of the war are still in evidence. Many farmhouses are ruins because they were shelled, and the contadini (farmers) couldn’t afford to restore them. But the peace and tranquillity that Origo loved when she first moved here in 1924 have returned. Arriving as a newlywed, aged 22, she was entranced by the weirdness, “a lunar landscape, pale and inhuman”. Old photographs show how barren it was back then, with not a tree in sight. Having bought an estate of some 3,500 acres, with its 25 farms, Iris and her Italian husband, Antonio, were determined to lift it out of poverty, “to turn this bare clay into wheat fields, to rebuild these farms and see prosperity return . . . to restore the greenness of these mutilated woods”. They built a school for the estate’s children, and a canteen for the workers.
Origo was raised in Florence, where her English mother rented the Villa Medici, one of the grandest houses in Fiesole. Origo’s father was American and immensely rich, but died when she was seven. Her mother then married Geoffrey Scott, a young Englishman who had set up an architectural firm in Florence with another Englishman, Cecil Pinsent, who designed many of the finest gardens in Tuscany. Origo’s teenage friendship with Pinsent led her to commission him to create the now famous gardens at La Foce, perhaps his greatest legacy.
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Two of the children Origo carried to Montepulciano in June 1944 were her own: Benedetta, three, and Donata, whose first birthday was celebrated with a children’s party as “planes drone overhead and swoop down on the valley roads”. After their mother’s death in 1988 they took over running the estate at La Foce, and in recent years have completed a top-to-toe renovation of the main house, which is available to rent as a 12-bedroom holiday home. The gardens are open to the public on certain days in summer, and on a recent visit I was delighted to turn a corner and see a house party of Californians sunbathing by the pool.
Hurrying on, the visitor is taken past the main façade of the house to Pinsent’s triumphant achievement: a series of box hedge “rooms” divided by gravel paths leading to a stone balustrade. Beneath unfolds the culmination of his design, a geometric box parterre planted to manipulate perspective so that it seems even grander than it is. Beyond a row of cypress trees stands Monte Amiata, the extinct volcano that marks the highest peak in Tuscany, towards which the eye is drawn wherever you are in the Val d’Orcia.
The forests that once covered it were said to have provided the timber to fight Hannibal during the Second Punic War. To your right lies another of Pinsent’s triumphs: that zigzagging white road lined with cypress trees, the first of its kind in Tuscany. For it was Pinsent who came up with the idea, planting this one as an ornament to the then featureless landscape. Since then it has been copied and repeated all over Tuscany, and is now as famous as Chianti wine or Michelangelo’s David.
As the eye wanders south, towards the medieval tower of Radicofani, it lands on another ancient feature of the Val d’Orcia — a flock of sheep grazing on a grassy hill. Their milk is used to make delicious pecorino cheese (it’s easy to remember the word for a sheep in Italian, pecora, from which the cheese gets its name). Even in the humblest supermarket here you’ll find a chilled cabinet stuffed with round wax-covered cheeses the size of side plates. There are three main varieties: staggionato, a dry, well-seasoned hard cheese with strong nutty flavour, best eaten after dinner; semi-staggionato, which has a milder flavour and medium-firm texture, recognisable for its orange rind and perfect as a pre-dinner snack; and fresh pecorino, which is springy and light and has not been matured at all — this you eat in the early spring, when the broad beans are in season; a plate of bright green baccelli e pecorino is a sign that spring has arrived in Tuscany.
The cheese-making capital is Pienza, one of the most perfect hilltop towns. Perfect because it was built all at once, in 1460, along humanist ideals, and never conquered, so it retains a rare architectural integrity. Originally named Corsignano, it became Pienza after its reconstruction by Aeneas Piccolomini, who later became Pope Pius II (Pienza meaning “city of Pius”). The elegant Renaissance streets are crammed with charming trattorias serving hearty winter stew (peposo) and Tuscan bean soup (ribollita). The church on the main piazza is a feat of engineering: it’s built on a rock, and in recent years the rear wall has been sliding off so that giant metal staples in the marble floor now keep half the church from falling away.
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Pienza is the ideal base for exploring the Val d’Orcia because it’s also home to La Bandita Townhouse, a stylish boutique hotel in the middle of town. The 12-bedroom property was fashioned out of an old nunnery by John Voigtmann, a former New York record executive, and his wife, Ondine Cohane. Voigtmann is passionate about Pienza and the Val d’Orcia, which he describes as “Tuscany for people who are deliberately avoiding the main sites”. He is in large part responsible for making it a destination of choice for the cognoscenti in recent years, having opened La Bandita Countryhouse in 2007, a sort of “anti-resort party house hotel”, as he calls it, and the Townhouse in 2013.
“Everywhere is a bit more discovered nowadays, but I would say this area is still not even in the top ten of Tuscan destinations,” Voigtmann says. “It’s obviously always been here, but it’s still a gem that has been slightly underappreciated.” With his eye for a clean and modern interior — framed album covers hang on the walls — both Banditas offer a refreshingly modern place from which to explore this ancient landscape.
No visit to Tuscany would be complete without a glass or three of wine, and here too the Val d’Orcia is beginning to pop up on the in-crowd’s radar. Sandwiched between the two more famous wine- growing regions of Montepulciano and Montalcino, home of the wildly popular (and madly expensive) brunello, for years the Orcia valley has been overlooked. One person hoping to change that is Tim Manning, 50, an English oenologist who has recently taken over winemaking at Fabbrica Pienza, a small organic vineyard overlooking Pienza belonging to Swiss wine lovers Tonie and Philippe Bertherat.
“This is an area that has always lived under the shadow of these two greats on either side,” Manning says. “As a result, people historically made other things here. But the topography and geology are actually very similar, and with winemakers looking to develop new areas, Orcia has the potential to do just as well.” Fabbrica Pienza is undergoing a renovation, with 11 bedroom suites planned for next spring, and Manning’s first wines due to be released this winter.
Eating and drinking occupy a lot of one’s time here. Go for lunch at Dopolavoro, the former canteen at La Foce built in 1939, now an excellent restaurant, for simple dishes such as a chunky deconstructed panzanella (tomato, red onion and bread salad) or mortadella with stracchino cheese and pistachio. Digest on one of several walking trails connecting the towns of San Quirico d’Orcia, Monticchiello and Montepulciano, and round off your day with a sundowner at Idyllium, a surprisingly hipsterish bar recently opened just inside Pienza’s city walls. The cocktails are new and the clientele young, but the view that stretches towards Monte Amiata is timeless — the Tuscany of one’s dreams.
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Seven nights’ self-catering for five in a two-bedroom property, with access to a swimming pool, from £1,403; seven nights’ self-catering for 24 in 12-bedroom Villa Origo from £24,000 (lafoce.com); B&B doubles at La Bandita Townhouse from £276 (la-bandita.com). Fly to Florence or Perugia
Ten more Tuscan holidays
1. On the trail of Piero della Francesca
The arcaded piazzas of Arezzo are worth seeing for their own sake, but they also form the starting point of a trail that follows the life journey of the groundbreaking 15th-century painter Piero della Francesca. Admire his frescoes depicting the creation of the cross in the church of San Francesco and his Maddalena in the Duomo, then see his most popular work, La Madonna del Parto, in the tiny town of Monterchi. Carry on to Sansepolcro, his birthplace and home to his masterful depiction of the resurrection. Stay at Badia di Pomaio, a converted 17th-century monastery on a hill overlooking Arezzo.
Details B&B doubles from £291 (badiadipomaio.com). Fly to Florence
2. Explore the wild beauty of the Maremma
When people think of Tuscany they rarely think of the seaside, but its coastline stretches some 155 miles along the Tyrrhenian Sea. The flat marshland of the Maremma is home to many species of bird and butterfly, rising to rolling hills inland. Here the Etruscans and Romans grazed their cattle. Base yourself near the hilltop town of Capalbio and visit the Tarot Gardens at Garavicchio, a fantasy wonderland created by the surrealist sculptor Niki de Saint Phalle. Locanda Rossa, a jaunty hotel and villas with swimming pools, is a five-minute drive from Capalbio.
Details B&B doubles from £161 (locandarossa.com). Fly to Rome
3. Chianti’s crazy wine cantinas
Tuscany’s noble families are intensely competitive, especially when it comes to their wines, and in recent years they have taken to building ever more outlandish wineries. So now you can combine art and architecture with wine tasting. Start with the Antinoris’ swooping lair cut into the hillside overlooking the motorway south of Florence, then head to the Mazzei family’s vast cellar sliced into rocks beneath the village of Fonterutoli. Finish at Tenuta Vallocaia in Montepulciano, a spectacular new “vinoteca” by the Swiss entrepreneur Rudi Bindella decorated with art from his own collection.
Details Two nights’ B&B at Castello di Fonterutoli from £351, including a wine tour lunch (castellodifonterutoli.com). Fly to Florence
4. The monasteries of Montalcino
The ancient pilgrim route from Canterbury to Rome, the Via Francigena, passes through the most beautiful scenery in Tuscany. The best section lies between the hill towns of Montalcino and Chiusure. Start with the hauntingly peaceful abbey of Sant’Antimo, founded by Charlemagne in 781, then visit the active monastery of Monte Oliveto Maggiore, where 40 monks occupy a building fit for 500. Don’t miss the frescoes by Sodoma and Signorelli; finish with a truffle lunch near by at the excellent Torre di Monte Oliveto restaurant. Massimo Ferragamo’s five-star Rosewood Castiglion del Bosco hotel comes with a winery and golf course and is a 15-minute drive from Montalcino.
Details B&B doubles from £655 (castigliondelbosco.com). Fly to Florence
5. Shopping in Montevarchi
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OK, so you probably didn’t visit Tuscany to browse designer handbags, but take a day off from frescoes to go bargain-hunting in the warehouse emporium of Prada — its Space outlet store at Montevarchi has acres of shoes, clothes, bags and accessories for a fraction of the usual price. If you’re hungry for more, the Mall is Florence’s answer to Bicester Village — all the biggest fashion labels, from Gucci to Salvatore Ferragamo, offer their wares in a spookily futuristic purpose-built retail park. Stay at Badia a Coltibuono, an 11th-century abbey, farm and cookery school between Montevarchi and Gaiole in Chianti.
Details B&B doubles from £115 (coltibuono.com). Fly to Florence
6. Marble quarries of Carrara
Up in the northwest corner of Tuscany, on the border with Liguria, lies the most visceral connection with the sculptures of the Italian Renaissance: you can see the mines being excavated for the same marble that Michelangelo’s David was made from. Drive past the docks of Massa, where slabs of marble stand ready to be shipped around the world, then up to the town of Carrara, from which the famous pale white-grey stone takes its name, for a guided tour of the open-cast mines. Villa Roma Imperiale in Forte dei Marmi offers light and airy family-friendly rooms with a pool and charming atmosphere.
Details B&B doubles from £383 (villaromaimperiale.com). Fly to Pisa
7. The private gardens of Florence
The British have long settled in Florence, but never more so than in the 19th and early 20th centuries — in 1911 they numbered 35,000. Villas in the hills of Fiesole and Arcetri were popular; here they had gardens laid out by Cecil Pinsent, a pioneer of the neoclassical. Many now belong to American universities but open to the public for a few days a year. Highlights include Harold Acton’s La Pietra, Bernard Berenson’s I Tatti, the Villa Gamberaia and the Villa Medici in Fiesole, a Renaissance triumph whose geometric simplicity was widely imitated. The Hotel Torre di Bellosguardo, a privately owned villa with gardens, has the best views overlooking Florence.
Details B&B doubles from £220 (torrebellosguardo.com). Fly to Florence
8. The grand villas of Lucca
The perfect walled city of Lucca is conveniently close to Pisa airport and the beaches of Viareggio and Forte dei Marmi. Many of Tuscany’s richest families have, over the years, favoured this rolling landscape for their country houses, so the area is dense with magnificent palazzi. Grandest of all is perhaps the baroque Villa Torrigiani, approached up a dramatic avenue of cypress trees. The Villa Oliva features a double-height loggia, as does the Villa Mansi, with its elaborate sculptures. The Villa Reale di Marlia wins for its water features and lovely camellias.
Details Three nights’ self-catering for five at Villa Grabau from £550 (aranceravillagrabau.it). Fly to Pisa
9. Unlock the Da Vinci Code
Or at least visit the Val di Chiana, an unspoilt valley on the Umbrian border where Leonardo planned to build a dam and series of canals, as depicted in a map housed in the Royal Collection. The pretty town of Cortona makes a great base for exploring the area, and next year marks the opening of Palazzo Passerini, a charming townhouse being converted into a luxury retreat by the hotel guru Lulu Townsend. Meanwhile, the recent renovation of Castello di Reschio just over the border in Umbria is still the hottest destination in Italy.
Details B&B doubles at Castello di Reschio from £672, minimum two-night stay (reschio.com). Fly to Perugia
10. Take the thermal waters
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Few things are stranger than wandering along a wooded path in winter and discovering a stream of boiling-hot water coming out of the ground. Such are the joys of the quietly volcanic landscape as in southern Tuscany. Wildest of all are the natural hot springs at Bagni San Filippo. The water is invitingly piping hot and, best of all, free to enjoy. Head to Bagno Vignoni afterwards for an excellent lunch in the piazza, where you can admire the vast stone bathing reservoir enjoyed by the Romans. The Relais Il Chiostro di Pienza, a 13th-century former convent in the heart of Pienza with cloisters and a pool, is the place to stay.
Details B&B doubles from £99 (relaisilchiostrodipienza.com). Fly to Florence or Perugia
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