Rosewood Castiglion del Bosco is a medieval borgo and its 900-year-old, 5,000-acre (~2,000-hectare) agricultural estate in the UNESCO-listed Val d'Orcia, restored from 2003 by Massimo and Chiara Ferragamo and managed by Rosewood since 2015. 42 suites and 11 villas, a two-Michelin-star table (Campo del Drago, chef Matteo Temperini), one of the historic producers of Brunello di Montalcino, and Italy's only private golf club — 18 holes by Tom Weiskopf. Hotel distinction: 3 Michelin Keys.
The Ferragamo Family's Tuscan Wager
In 2003, Massimo Ferragamo — of the Florentine dynasty — bought Castiglion del Bosco: a medieval borgo with its tower and frescoed chapel, 17th- and 18th-century farmhouses, and one of Tuscany's largest intact agricultural estates. Twelve years of restoration later, in 2015 it became Rosewood's first Italian address. The result is not a hotel in the countryside but an entire countryside — vines, forests, kitchen gardens — organised around a borgo brought back to life.
Estate Brunello, Two Michelin Stars
Castiglion del Bosco is one of the historic producers of Brunello di Montalcino: tasting seminars, winery tours and the 'Truffles and Brunello' experience happen at the winemaker's own estate, not a vendor's. At table, Campo del Drago — 2 stars in the 2026 Michelin Guide Italia, chef Matteo Temperini, a 700-label cellar — leads a line-up running from the Tuscan osteria (La Canonica) to in-villa dining.
Italy's Only Private Golf Club — and Villas Like Homes
The Club at Castiglion del Bosco is presented as Italy's only private golf club, reserved for members and hotel guests: 18 holes by Tom Weiskopf — his only Continental European design — plus a 19th 'Brunello hole'. The estate's 11 villas (private pools, Rosewood service) also make this one of Italy's great family addresses; suites run roughly 54–185 m². A seasonal house: closed in winter (the 2025 season ran to January 7, 2026, with winter villas rentable during closure), under an hour from Siena.
The Estate in Three Frames
Photos © Rosewood Castiglion del Bosco
The Offers the House Publishes
Public offers seen on rosewoodhotels.com on 28/08/2026 — content, conditions and availability are set by the house and confirmed at quotation. GADAIT applies whichever offers are in force at your booking.
What You Live at the Estate
The house programme, vineyard side and fairway side:
The Best Windows at the Estate
The house is seasonal: closed in deep winter (the 2025 season ran to January 7, 2026, with 'Winter Villas' rentable during closure), alive from March to the festive season. May–June for gardens and golf in the long light; September–October for the Brunello harvest, the autumn Golf Cup and the Fall Getaway offer; December for the festive formats (third night free, New Year's Eve at the estate).
Worth knowing: the 11 villas sell out months ahead for harvest weeks — the first thing we lock at quotation.
Rosewood Castiglion del Bosco in Numbers
| Estate | ~2,000 ha (5,000 acres), UNESCO Val d'Orcia — medieval borgo at its heart |
| Accommodation | 42 suites (≈ 580–2,000 sq ft) + 11 villas with private pools |
| Dining | Campo del Drago — 2 Michelin stars 2026, chef Matteo Temperini |
| Wine | Historic Brunello di Montalcino producer, Campo del Drago cru |
| Golf | The Club — 18 holes by Tom Weiskopf, Italy's only private club |
| Recognition | 3 Michelin Keys (Michelin Guide) |
| Season | Seasonal — closed in winter (winter villas available to rent) |
| Rates | On request — quoted by dates through your advisor |
Independent editorial page: information and directional rates come from the hotel's public materials and specialist sources, and must be confirmed at booking. Cited brands belong to their owners.
Book It the GADAIT Way
This house is part of the GADAIT editorial selection — addresses we know and recommend. We are not its representative: we organise your stay as your advisor, from availability requests to tables, experiences and transfers, and remain your single point of contact.
Luxury real-estate and stay advisory — official hotel partner of Monteverdi Tuscany, independent editorial selection for the other houses. Every fact on this page is sourced (Michelin Guide, the houses' public materials) and dated; pages are re-verified quarterly.
Our editorial method →FAQ — Rosewood Castiglion del Bosco
In the commune of Montalcino, at the heart of the UNESCO-listed Val d'Orcia, on an estate of roughly 2,000 hectares. Siena is under an hour's drive; the hotel has its own helipad, about 45 minutes' flight from Grosseto's private airport.
42 suites — from about 580 to nearly 2,000 sq ft, many with terraces larger than the suite itself — plus 11 one-of-a-kind villas with private pools, in high demand from families and groups. The scale stays confidential for an estate this size.
Yes. Campo del Drago, led by chef Matteo Temperini, holds 2 stars in the 2026 Michelin Guide Italia, with three tasting menus and a cellar of over 700 labels. Osteria La Canonica covers the trattoria side, and the house is itself a historic Brunello di Montalcino producer.
The combination has no equivalent: an intact 900-year-old agricultural estate, Brunello made on site, 3 Michelin Keys, a two-star table and Italy's only private golf club — 18 holes by Tom Weiskopf. It is the house for trips built around wine and golf.
GADAIT organises the stay as your advisor: availability requests, suite or villa selection, tables, experiences (winery, truffle, golf) and transfers, through one point of contact. The house is seasonal — opening dates and rates are confirmed at quotation.
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