A meandering, cypress-lined road leads to the Borgo, the historic heart of Rosewood Castiglion del Bosco’s bygone farming community. Located on a hilltop, overlooking patchwork fields that stretch out below towards Montalcino, the Borgo was the center of the estate’s activities for hundreds of years. Dominated by the ruins of the medieval castle that gives the estate its name, it is a place brimming with memories waiting to be explored. Within the Borgo, the historic manor house, old winery, stables, church of San Michele Arcangelo, priest’s house and other buildings have all been meticulously restored and repurposed. The village now features two restaurants, a cooking school, an organic kitchen garden, 23 luxury suites and 3 of the 11 exclusive Villas, a spa, an infinity pool and a fitness center. The Borgo houses priceless works of medieval and early-Renaissance art. The Annunciazione dei Santi (Annunciation of the Saints), a fresco by Pietro Lorenzetti of the Sienese School in the church of San Michele Arcangelo, was brought to light in 1876 and has been restored to its former glory.