Set deep in the Val d’Orcia, amid rolling vineyards and spectacular hillside scenery, Castiglion del Bosco is Tuscany at its most cinematic. Wake early to watch the landscape change as the early morning mist rises above the hills. This vast 5,000-acre estate, anchored by a beautifully restored medieval borgo, feels less like a hotel and more like a private Tuscan village, steeped in rich history and preserved with the utmost attention to detail.
Rooms and suites are housed in honey-coloured stone buildings; inside, you’ll find terracotta floors, plush beds and furnishings, generous terraces and far-reaching vineyard views. Villas with private pools up the ante for longer stays, and are perfect for families seeking privacy.
The culinary heart of the estate is the two-Michelin-starred Ristorante Campo del Drago, with a menu that champions refined, modern Tuscan flavours, but remains rooted in the surrounding landscape. Ingredients for dishes come from the estate and its neighbouring producers, with Brunello di Montalcino – produced at the Castiglion del Bosco winery on site – served alongside.
Ristorante Campo del Drago’s tasting menu is a work of art in its own right: expect dishes like turbot on the bone with leeks & olive, foie gras with pear & quince, or vegetable ravioli with pear, citrus & saffron. The hospitality is knowledgeable and warm, and the staff are charming and attentive across the whole hotel. Enthusiastic foodies can participate in Tuscan cooking classes and wine- tastings, or take a tour of the hotel’s impressive vegetable gardens.
For something more relaxed with thefamily, Osteria La Canonica delivers comforting Italian classics, including lobster ravioli, wood-fired pizzas and pappardelle with wild boar ragu.
For children, the scale of the estate is a major advantage – heated outdoor pools allow for comfortable swimming beyond the height of summer, while the open landscape provides space to explore and enjoy nature. Local deer move through the hotel grounds and are often found helping themselves to the plentiful garden. Older children and teenagers can enjoy complimentary bikes on designated cycling routes, giving them a sense of independence within a safe, contained environment.
Younger guests are also catered for through a supervised kids’ club, with activities focussed on outdoor play, creative workshops and simple cooking experiences. The staff are so engaging that even the shyest children will soon relax into their new surroundings.
And, while the children are cared for, parents can make use of the spa, which provides a quiet refuge for treatments and thermal experiences – like hot stone massages, facials and a sound bath – for the ultimate relaxing family escape.
How to book
For a seven-night stay at Castiglion del Bosco based on two adults and two children sharing a three-bedroom villa, or for other holiday packages, please go to castigliondelbosco.com for the latest pricing and offers.

