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Castiglion del Bosco: The jewel of the Val d’Orcia

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The Tuscan winery where hospitality meets winemaking excellence.

Meandering for some 50 miles from the hills south of Siena to Mount Amiata, the Val d’Orcia passes through breathtaking countryside, ancient hilltop villages, and vine-covered slopes. Among these beautiful surroundings sits Castiglion del Bosco, offering its guests hospitality with a touch of true glamour, as well as the finest expressions of Sangiovese.

Excellence steeped in history

Sitting at the heart of a UNESCO World Heritage Site and spanning 2,000ha of Tuscany’s heartlands, historic Montalcino estate Castiglion del Bosco has made a reputation for itself as a producer of award-winning Brunello and superb Rosso di Montalcino. With Cecilia Leoneschi at the helm as head winemaker, the estate boasts around 62ha planted to vine.

Recent successes at the prestigious Decanter World Wine Awards saw Castiglion del Bosco’s Brunello di Montalcino 2019 and Campo del Drago 2019 receive Silver medals; both were praised for their ripe red fruit character and complex notes of earth and leather.

Barrels in the Castiglion del Bosco cellar

An immersive approach to wine tourism

Castiglion del Bosco is also a strong contender for Italy’s finest countryside hotel, with an on-site winery, two restaurants, cooking school, spa, and a twin set of infinity pools. The ethos at this remarkable estate, combining the decadent and the informative, is designed to appeal to today’s oenophile: sophisticated and insatiably curious about the how and why of viticulture.

Castiglion del Bosco cleverly juxtaposes the nitty-gritty of a busy wine estate with glass-fronted tasting rooms, Tuscan fine dining and luxurious accommodation among the vines; sharing the stories of its unique wines and offering a new imagining of luxury tourism.

Exploring the Val d’Orcia from Castiglion del Bosco

One of the most rewarding ways to explore the Val d’Orcia is by bicycle, pedalling through the vines at your own pace and immersing yourself in the landscape. The slopes of extinct volcano Mt Amiata make for the perfect picnic spot; whilst for a bird’s eye view of the famous terroir, there is the option of booking a helicopter ride over the vineyards.

At harvest time, wine lovers have the chance to experience a working vineyard: every year, Castiglion del Bosco welcomes enthusiasts seeking a hands-on role in the vintage.

Castiglion del Bosco wines

Castiglion del Bosco’s Grand Cru hospitality

At Castiglion del Bosco, there are plenty of ways to whet the appetite before dinner: winery tours, cheese and wine pairings and vertical tastings. Then, for a delicious meal overlooking the verdant landscape of Montalcino, visitors are spoilt for choice. Osteria La Canonica prides itself on its relaxed atmosphere and traditional Tuscan fare. The Michelin-starred Ristorante Campo del Drago, on the other hand, serves avant-garde interpretations of regional classics using ingredients from the hotel’s gardens.

Meanwhile, you’ll be staying in some of Tuscany’s most sumptuous accommodation: 42 stylishly decorated suites and 11 villas, including the magnificent Villa Gauggiole, surrounded by a magical backdrop of woodland and vineyards.

Those seeking some down time can slow the pace right down – eat, drink, relax, repeat. But there is also an array of activities on offer for the adventurous, such as truffle hunting (in season), guided tours of Siena, horse riding and hiking. This pre-eminent Tuscan fine wine producer has now put its own stamp on 21st-century wine tourism, pairing luxury with authentic experiences.

A Castiglion del Bosco wine and food pairing

Beyond Montalcino

Castiglion del Bosco has another major advantage: it is just two hours by car to Tenuta Prima Pietra, a sister winery that boasts a gorgeous, sea-facing terrace and a plethora of tour and tasting options. Culture lovers, meanwhile, can book a trip to the splendid Palazzo Capponi in the heart of historic Florence. In this ancient and lovingly restored building, you can sip rare vintages of Brunello among Renaissance frescoes and Florentine masterpieces, making for a truly unforgettable experience.


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