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Decanter’s Dream Destination: Rosewood Castiglion del Bosco

Every month Decanter selects a must-visit destination for wine travellers. With its rambling villas, five-star service and Brunello di Montalcino made on site, this Tuscan wine estate and hotel is a must-visit.

Green undulating valleys, flecked by pin-straight pines and flanked by woodlands. Sun-drenched olive trees and slopes carpeted in vines. Sleepy villages, cluttered with medieval builds. And, perched at the top of a hill overlooking it all, Castiglion del Bosco.

Tuscan hotels don’t get any more picturesque than this 2,000ha estate. But Castiglion del Bosco wasn’t built to be a hotel. It certainly wasn’t built to be a Rosewood. The glossy American brand with impeccable luxury creds and a celebrity following only took over the estate’s accommodation offering in 2015. 

Turn the clock back a millennia and this remarkable hilltop enclave housed a medieval castle. A 14th-century painting by Pietro Lorenzetti remains preserved in the onsite church – now a museum-worthy selfie op for hotel guests. 

Vinous roots 

Castiglion del Bosco’s Capanna Vineyard

After falling into disrepair, the hamlet was purchased by fashion scion Massimo Ferragamo in 2003 and splendidly – down to the last bit of cobbled stonework and burnt orange roof tile – regenerated into a resort. He was drawn, as all wine-loving visitors will be, by Castiglion del Bosco’s deep connection to Brunello di Montalcino.

The estate has grown grapes for centuries, long before Tuscan wines were esteemed around the world, and in 1967 Castiglion del Bosco was one of the founding members of the Consorzio del Brunello di Montalcino. Its wine was among the first to achieve DOC status in Italy.

Visit Castiglion del Bosco today, and you’ll see that the connection continues to thrive. Once you’ve dropped your bags in your Rosewood suite or villa – 19 new but sympathetically designed stunners opened in August 2021, almost doubling the property’s number of rooms – you can be at the onsite winery and sipping on Sangiovese verticals within minutes. 

Of course, being in the heart of Brunello di Montalcino doesn’t mean staying put at just one winery. Rosewood knows as much; the hotel offers every kind of tailored wine-tasting experience you can hope for, whether you fancy a tour of top local producers normally closed to the public or, in autumn, a truffle hunting expedition followed by a decadent winery lunch. 

But its flagship wine experience? A full day helicopter tour over the surrounding Unesco-protected Val d’Orcia, including a stop at biodynamic Podere Le Ripi winery and lunch at Michelin-starred restaurant Silene. Basically, with their connections, there’s not much the Rosewood staff can’t pull off. 

Food, feasts and relaxation 

Once you’ve had your fill of exploring, back at the hotel you can lay into full-scale indulgence. There are two Italian restaurants, serving the likes of hare pappardelle, Tuscan pigeon with pomegranate glaze and, of course, crowd-pleasing pizza. 

In summer, long-table dinners are held open-air in the organic kitchen garden, so you can feast on freshly plucked veg as the sun sinks below the hills. Wherever and whenever you’re dining, wine is a key part of it. In fact, the hotel endeavours to list every one of the Brunello region’s 240 producers. (Whether you can actually order them all is another matter; stock varies depending on when you visit.) 

Because the grounds are rambling, and the guest numbers are comparatively few, the Rosewood never feels crammed, whether you’re sipping a cocktail by the pool overlooking the Val d’Orcia or getting a lavender-scented massage in the serene spa. 

But for ultimate space and tranquillity, trade one of the suites – dressed in typically Tuscan deep reds, golden yellows, soothing creams – for an even more spacious villa. These restored 17th and 18th-century farmhouses, large enough for a big family, come with heated infinity pools, ‘mamas’ (a homely maid-meets-butler service) and, in some cases, tennis courts, jacuzzis and home theatres. In other words, only the good old fashioned Tuscan essentials…

For more information visit www.rosewoodhotels.com/en/castiglion-del-bosco

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