Castello di Casole—a Timbers Resort
A cypress-lined road leads to the main building of this rolling 4,200-acre Tuscan estate, a restored castle that dates back to the 10th century. Now owned by Timber Resorts, Castello di Casole was once the home of film director Luchino Visconti and hosted countless Hollywood luminaries. The 41 rustic-luxe suites range in size and style but retain an Old World feel throughout, with oil paintings, local antiques, wood-beamed ceilings, and reclaimed terracotta. The Essere Spa, set in what was once the estate’s wine cellar, offers an array of treatments including the hotel’s signature massages with orange and basil essential oils. Be sure to leave plenty of time for lounging on the pool terrace to take in the expansive views of the surrounding Tuscan hillside (and perhaps a glass or two of the estate’s private label wine).