Luxury Hotel Pick: Rosewood Castiglion del Bosco in Tuscany, Italy

Spotlight on luxury: today, we’re featuring the unique Rosewood Castiglion del Bosco in Tuscany, Italy.

Where is Rosewood Castiglion del Bosco?

Nestled in Montalcino, Tuscany, in the heart of the UNESCO World Heritage Site of Val d’Orcia, Rosewood Castiglion del Bosco is set within a 5,000-acre 900-year-old Italian estate. Just south of Siena, approximately 2 hours from Florence and 2.5 hours from Rome.

When was Rosewood Castiglion del Bosco built or updated?

The estate’s origins date back to around 1100 A.D. and feature historical elements such as 12th-century castle ruins and a 14th-century church adorned with Pietro Lorenzetti’s fresco, “Annunciazione dei Santi.”

In 2003, Massimo and Chiara Ferragamo acquired the estate and transformed it into a luxury resort, which opened to guests in 2010. In 2015, the resort became part of the Rosewood Hotels & Resorts collection.

Significant renovations and expansions were undertaken to enhance the property’s offerings in 2021, including 19 new private suites and the renovation of the Osteria La Canonica restaurant. In 2023, nine of the eleven private villas were comprehensively renovated.

These updates have solidified Rosewood Castiglion del Bosco’s reputation as a premier destination that seamlessly blends historical charm with modern luxury.

Why stay at Rosewood Castiglion del Bosco?

Rosewood Castiglion del Bosco is an exceptional gastronomic retreat, home to two acclaimed restaurants, an organic kitchen garden, and a hands-on cooking school. Set within a storied estate, the resort also boasts evocative ruins of an ancient castle, a historic medieval church, a tranquil spa, a modern fitness centre, and a wide array of leisure amenities. Curated experiences and excursions immerse guests in the region’s breathtaking landscapes and rich cultural heritage.

Bathed in the warm, earthy tones of Tuscany, the resort’s expansive suites and villas provide refined comfort amid extraordinary natural beauty. The 42 suites are designed with a sense of harmony featuring antique furnishings, authentic textiles, artisanal accents, exposed wooden beams, and inviting nooks—seamlessly blended with contemporary luxuries and technology. Outdoor spaces such as terraces and pergolas frame sweeping countryside views, vibrant with lush greenery.

Crafted from restored 17th- and 18th-century farmhouses, the 11 private villas embody the spirit of the Tuscan landscape. Rich in character, they feature stone and wood architecture, Sienese-inspired hues, custom-made furniture, and handcrafted details. Each villa offers three to six bedrooms, a private heated pool, and select amenities such as a pool house, private tennis court, or home cinema, making them ideal for families or groups seeking privacy and elegance.

How to get to Rosewood Castiglion del Bosco?

For those driving from the south, please follow the route to Montalcino. Once you reach Montalcino, please set your sat map towards Rosewood Castiglion del Bosco.

For those arriving from the north (Florence, Siena or SR2) please follow the route Siena to Grosseto. At Fontazzi take the exit for Casciano and continue towards Vescovado/Murlo until you reach Bibbiano, where you may set your sat map towards Rosewood Castiglion del Bosco.

Do you want to know about the nuts and bolts?

Rosewood Castiglion del Bosco offers 42 suites that exude a rich sense of authenticity, with heritage features, antique furnishings, local textiles and artisanal accessories. In addition, 11 one-of-a-kind luxury Tuscan villas dot the landscape, each created from restored 17th- and 18th-century Tuscan farmhouses. These private homes provide luxurious lodging and feature heated pools, terraces, pergolas and gardens—all framed by the unmatched natural beauty of the Tuscan countryside.

How does the Rosewood Castiglion del Bosco describe their room style?

The resort’s 42 spacious suites fuse authentic Tuscan heritage with modern comforts. Exposed wooden beams and antique furnishings complement the latest technology. Terraces, pergolas, and picturesque views are alive with greenery.

Eleven one-of-a-kind villas dot the countryside at Rosewood Castiglion del Bosco. Crafted from 17th- and 18th-century farmhouses and lovingly restored, these wonderfully private homes feature heated infinity pools, terraces, and gardens with views of the beautiful Tuscan landscape. Villas boast fully equipped kitchens by Florentine designer Riccardo Barthel and come with a 7-seat Land Rover Defender, or a similar type of 4×4 vehicle, for guests to use during their stay.

Want to hear something unique about Rosewood Castiglion del Bosco?

Rosewood Castiglion del Bosco offers an authentic farm-to-table culinary experience that immerses guests in Tuscany’s rich flavours and traditions.

At the heart of the resort’s culinary philosophy is its organic kitchen garden, meticulously designed in a quadrangle layout inspired by medieval enclosed gardens. This garden overflows with fresh vegetables and savoury herbs native to Tuscany, cultivated following strict organic guidelines and centuries-old agricultural practices. The produce harvested here serves as the foundation for many dishes at the resort’s restaurants and cooking school. 

The property was also part of the Sienese Republic at one point and was the scene of armed assaults in the 13th century.

Who manages Rosewood Castiglion del Bosco?

As of March 1, 2025, Nicola Migheli serves as the Managing Director of Rosewood Castiglion del Bosco, a luxury resort located in Montalcino, Tuscany. Prior to this role, Nicola was the resort’s Hotel Manager, where he played a pivotal role in enhancing guest experiences and operational excellence. With over 20 years of experience in luxury hospitality, he has held key leadership positions in London, Dubai, Sardinia, Puglia, and Veneto. Nicola holds a Bachelor’s degree in Economics & Management of Tourism Services from the Università degli Studi di Cagliari.

What luxury deal can Traveloso provide you?

Via our Virtuoso affiliation, we can access exclusive rates that include a room upgrade on arrival, daily buffet breakfast, at least $100 USD equivalent resort credit, early check-in / late check-out, and Complimentary Wi-Fi

There are also some other benefits that can potentially be added.