#1 in Top 20 Tuscany for an Anniversary · ★★★★★
Rosewood Castiglion del Bosco
Massimo Ferragamo's 5,000-acre Brunello estate near Montalcino, 42 suites and 11 villas, the flagship Tuscan anniversary.
Massimo Ferragamo's 5,000-acre Brunello estate near Montalcino, 42 suites and 11 villas, the flagship Tuscan anniversary.
Rosewood Castiglion del Bosco is Massimo Ferragamo's 5,000-acre Brunello estate near Montalcino, a restored medieval borgo of 42 suites plus 11 private villas in the UNESCO-listed Val d'Orcia. For an anniversary it delivers privacy, two-Michelin-star dining and an estate winery, at the very top of the Tuscan market.
Our editors score every property from 1 to 10 across six criteria, Romance, Service, Value, Design, Food and Location, then weight them by how the hotel is used. For an anniversary we weight Romance, Food and Service most heavily. Castiglion del Bosco takes an aggregate 9.9. See our full methodology.
Castiglion del Bosco is the answer for a milestone anniversary that wants privacy and a genuine sense of place rather than a busy resort. Massimo Ferragamo, son of Salvatore Ferragamo, bought the roughly 5,000-acre, 900-year-old estate in 2003; it opened as a hotel, spa and golf resort in 2010 and joined Rosewood in 2015. The estate sits in the heart of the UNESCO-listed Val d'Orcia and Brunello di Montalcino wine country, and it produces its own Brunello DOCG. The appeal for a couple is space and seclusion: a restored medieval borgo of 42 suites, plus 11 private villas with pools scattered across the hills. The estate winery runs cellar tastings, the two-Michelin-star Ristorante Campo del Drago is the special-occasion dinner, and Sense, A Rosewood Spa handles the slow mornings. There is also Italy's only private golf club, an 18-hole course designed by Tom Weiskopf. The honest trade-off is that the estate is vast and genuinely remote, so a car is useful and getting between corners of it takes time, and rates sit at the very top of the Tuscan market.
The recognition backs up the experience: in Travel + Leisure's 2026 World's Best Awards, readers voted Castiglion del Bosco the best hotel in Europe, an unusually strong signal for a property whose whole pitch is quiet rural seclusion rather than city buzz.
Accommodation splits into two very different experiences. The 42 suites occupy the restored stone buildings of the borgo, the medieval hamlet at the estate's core, so you are steps from the main pool, the restaurant and the piazzetta, with the sociable heart of the property on your doorstep. The 11 private villas are the seclusion play: standalone houses spread across the estate, most with a private pool and full staffing options, ideal for a couple who wants total privacy or a family group taking a whole house. For an anniversary, the decision is simple: take a villa with its own pool when you want to disappear together, or a borgo suite when you would rather be close to the restaurant and the evening scene. Interiors throughout lean into the estate's own materials, terracotta, stone and Tuscan textiles, rather than a generic five-star look.
Reserve Ristorante Campo del Drago well ahead for the anniversary dinner and book a cellar tasting of the estate's Brunello, ideally paired with a vineyard walk. Leave a slow morning for Sense, A Rosewood Spa or a round on the Tom Weiskopf course, and ask the concierge about the estate cooking school if you want a hands-on afternoon.
Dining is a genuine reason to come. Ristorante Campo del Drago holds two Michelin stars and cooks refined Tuscan food built almost entirely from the estate's own gardens and the surrounding region, the natural centrepiece for an anniversary dinner. For relaxed meals there is the trattoria-style Osteria La Canonica and a seasonal pool bar. Beyond the table, the estate is a working Brunello di Montalcino producer, so cellar tastings and vineyard visits are part of the offer rather than an add-on, and there is a Tuscan cooking school for those who want to learn. Sense, A Rosewood Spa provides the wellness half, and the main infinity pool looks out over Montalcino and the Val d'Orcia. The private 18-hole Tom Weiskopf golf course, the only one at a members' club of its kind in Italy, rounds out the estate for guests who play.
Against the rest of our Tuscany anniversary list, Castiglion del Bosco is the estate-and-winery flagship. The table sets it beside three strong alternatives.
| Property | Best for | Style | From |
|---|---|---|---|
| Rosewood Castiglion del Bosco | Privacy, wine and two-Michelin-star dining | 5,000-acre Brunello estate with borgo and villas | €1,400 |
| Belmond Castello di Casole | A restored castle estate near Volterra | Hilltop castle hotel with vast grounds | €900 |
| Borgo Santo Pietro | Farm-to-table romance and gardens | Restored villa and working farm near Siena | €1,000 |
| COMO Castello Del Nero | Chianti wine-country polish and spa | Renaissance castle hotel in Chianti | €850 |
The choice comes down to the kind of estate you want. Castiglion del Bosco is unmatched for the combination of a working Brunello winery, two-Michelin-star dining and private villas, and it prices accordingly. Belmond Castello di Casole and COMO Castello del Nero deliver castle grandeur for less, and Borgo Santo Pietro is the pick if farm-to-table romance and gardens matter more to you than golf and a winery.
Recent verified reviews are unusually consistent. Guests single out the setting, the sense of a genuine working estate rather than a manicured resort, and the service, which is repeatedly described as attentive without being intrusive. Campo del Drago draws praise as a destination dinner, and the villas are called out for privacy. The recurring caveats are practical rather than critical: the estate is large and spread out, so you rely on buggies, shuttles or a car to move around, and everything, from dining to the spa to activities, comes at premium pricing. Couples who understand they are paying for space, wine and seclusion tend to rate the stay at the very top; those expecting a compact, walk-everywhere hotel are occasionally surprised by the scale.
Even at this level, there are honest trade-offs worth naming before you book.
For a peak-season anniversary, secure the room three to four months ahead; the villas and the best borgo suites sell through first, and Campo del Drago should be booked at the same time as the room. Late spring and early autumn deliver the Val d'Orcia at its most beautiful with slightly gentler rates than high summer. Confirm whether you want a villa or a borgo suite based on how much seclusion versus proximity you want, and line up the winery tasting, a spa morning and, if you play, a round on the Weiskopf course when you reserve.
Massimo Ferragamo, son of Salvatore Ferragamo, bought the 5,000-acre estate in 2003. It opened as a hotel, spa and golf resort in 2010 and joined Rosewood Hotels and Resorts in 2015, becoming Castiglion del Bosco, A Rosewood Hotel.
The resort has 42 suites in the restored medieval borgo plus 11 private villas across the estate, most with their own pool. A villa gives the most seclusion; a borgo suite keeps you closest to the restaurant and main pool.
Yes. Ristorante Campo del Drago holds two Michelin stars and cooks refined Tuscan dishes from the estate's gardens. There is also the trattoria-style Osteria La Canonica and a seasonal pool bar.
Yes. Castiglion del Bosco is a working Brunello di Montalcino producer with its own vineyards and cellar, and guests can book tastings. The property also has Italy's only private golf club, an 18-hole Tom Weiskopf course.
The estate is in the Val d'Orcia near Montalcino, roughly 75 minutes by car from Florence airport and about 40 minutes from Siena. It is rural and spread out, so a car or the hotel's transfers help.
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