Tuscany’s Wonderland: Exclusive Resort With Ties To The Middle Ages Dazzles

Several years ago, I spent a few weeks in Italy, landing in Florence and making my way to Tuscany and Umbria, spending most of the trip at an agriturismo above Assisi. Someday I plan to make up for my lack of attention to Tuscany, and when I do, I will stay at Rosewood Castiglion del Bosco.

Why? For starters, it’s owned by Massimo Ferragamo, chairman of Ferragamo USA, and his wife, Chiara, so you know its 23 suites and 10 villas are full of style, with stone-floored kitchens, exposed wooden beams and antique furnishings.

Then there’s this: Castiglion del Bosco is an 800-year-old estate on 5,000 acres that includes the ruins of a castle and a church built in the Middle Ages, as well as a winery producing Brunello di Montalcino, two restaurants and a cooking school. My friends and I will book a villa (one with a wood-burning pizza oven) and explore the countryside, taking trips to nearby Florence and Siena, returning in the evening for a meal and perhaps a cooking class. Our heated private pool will be ideal for a late-night swim in the open air. We’ll be refreshed, open some great bottles of wine and head home happy.

Suites from $1,607 per couple, villas from $5,562 per night, at rosewoodhotels.com/en/castiglion-del-bosco.