Good for: Solo travelers, honeymooners, groups of friends and families. Come one, come all.
When to go: Optimal times are late spring, summer and fall. Winter is quiet – almost all of the vineyards are closed unless you arrange private tastings with owners who are still in town. There is a comfort to taking a retreat here though any time of year. 
Suggested Stay: 3-4 days, or up to a week, if you really want to decompress.
Located in the heart of Tuscany, it’s arguable that Castiglion Del Bosco is the most stunning place in all of the region. This speaks volumes, because anyone who has been to Tuscany knows there is some steep competition. The 5,000-acre country estate was founded by Massimo and Chiara Ferragamo, and is now a part of the Rosewood portfolio – so what was already perfection, is now even better.
Located within the UNESCO-listed Val d’Orcia in the Brunello di Montalcino region, the 800-year-old estate consists of ancient castle ruins, a medieval church, a historic village at the heart of the resort, a spa, a winery, and vineyards – pretty much everything you can ask for in life. To stay, it’s smaller than you think, with twenty-three suites, and eleven luxury villas – which are created from restored 17th and 18th-century farmhouses. Each room is deeply comfortable: you feel as though you’re staying in a well-held friend’s home. With the location , you can easily take day-trips to Montalcino, which is home to the Brunello, or even walk to the neighboring vineyards, should you want to stick close.
Activities:
Of many notes, the hotel is equipped with a cooking school, which can teach just about anyone how to make authentic Tuscan cuisine, from the simplest pasta to an elaborate feast. For those who like to leave cooking to the professionals, the 18-hole golf course, designed by Tom Weiskopf, is an experience in Italy’s only private golf club. Additional pursuits include horseback riding, yoga, Pilates, nature walks, circuit training, mountain biking, bocce ball, and archery. You know, all in a day’s work.
