Best hotels in Siena & Val d'Orcia

Somewhere in the rolling countryside southwest of Siena, down a long gravel drive lined with cypresses, sits an 800-year-old villa that once nursed medieval pilgrims back to health. Today it performs a similar service, albeit with Michelin-starred dinners and a spa that produces its own skincare line. Danish owners, Claus and Jeanette Thottrup, have spent two decades transforming the estate into a 300-acre working farm with vineyards, an artisan dairy, kitchen gardens and even alpacas. The result is a place is lived-in rather than designed, where the flowers on your bedside table were picked that morning and the cheese at breakfast was made down the hill. And it's all effortlessly lovely.

The property boasts Italy's only private golf club, a renowned Brunello di Montalcino winery, gourmet dining, and a serene spa. Despite world-class amenities, the estate maintains an intimate atmosphere where guests can experience the timeless beauty of Val d'Orcia while enjoying exceptional privacy and personalized service.

Imagine waking up in an 8th-century hamlet, where geraniums spill from stone windowsills and the morning mist slowly reveals Siena's striking silhouette in the distance. This isn't just any village though - it's a rather spectacular Relais & Châteaux property where every medieval building, from the chapel to the cobbled square, has been carefully transformed into something truly special. The active winery and surrounding vineyards aren't just for show either - they produce some seriously good bottles that are shipped across the globe.

Perched among rolling hills and ancient vineyards, this 1000-year-old castle has perfected the art of combining historic grandeur with laid-back Italian charm. Think exposed stone walls, beamed ceilings, and the kind of views that make you want to quit your job and become an olive farmer. The castle's courtyard feels like it's been plucked straight from a Renaissance painting, while the Michelin-starred restaurant proves that modern-day pleasures haven't been forgotten. Whether you're hunting for truffle-laden pasta or simply fancy a splash in the panoramic pool, this pocket of Tuscany knows how to deliver the goods.

Ever dreamt of living like 16th-century nobility? Step through the doors of this magnificent palazzo and you'll find yourself transported back in time to when members of the powerful Chigi family roamed its hallowed halls. Originally gifted by Pope Alexander VII to his niece as a rather lavish wedding present, today it stands as the only five-star hotel within Siena's ancient walls. Just a stone's throw from the iconic shell-shaped Piazza del Campo and the striking zebra-striped Duomo, you're perfectly positioned to soak up the city's medieval splendour. Inside, original frescoed ceilings, cotto tile floors worn smooth by aristocratic footsteps, and antique chandeliers create an atmosphere that whispers of bygone opulence while catering to modern luxury-seekers.