Tuscany’s renowned strade bianche (white roads), a network of unpaved motorways that are dusty in summer, undulate through the region’s famously gorgeous vineyards and olive groves. Follow one of the old white roads from Bibbiano and you’ll soon find yourself in a truly magical place: Castiglion del Bosco. Known in English as Castle in the Woods, it was once a medieval Italian village; today, Massimo Ferragamo, son of the famous shoemaker and chairman of the fashion brand’s American division, has transformed it into possibly the most perfect hotel in the world. Be prepared to eat and drink your way to gastronomic nirvana here, especially if you’re a fan of the famed Tuscan red, brunello di Montalcino. Castiglion del Bosco is connected to a 62-hectare wine estate and guests can take part in the harvest, as well as guided tastings, plus classes at the in-house cookery school. There’s six kilometres of bumpy white road before you reach the gates of the old village-cum-resort, but the slow going is rewarded with fabulous scenery. The hotel is set within a 5,000-acre estate surrounded by fields and forest, a former private hunting reserve, which still teems with wild boar, deer, foxes and hare. From the highest point on the road, there are views across the Val d’Orcia (Tuscany’s most revered valley) to the fortressed town of Montalcino. And beyond the forest you can see vineyards, centuries-old farmhouses and rambling driveways edged with cypress trees.

The road is, in fact, the old Via Francigena, which took crusaders and merchants from Canterbury to Rome. The village of Castiglion del Bosco, which intersects the road and is known simply as Il Borgo, was built in 1100, then taken over by the Galleranis, a prosperous merchant family, in the 14th century. (Cecilia Gallerani is Leonardo da Vinci’s subject in The Lady with the Ermine.) It continued to change hands over the centuries, but became derelict in the 18th century. Massimo Ferragamo, nostalgic for the Tuscany of his childhood, purchased the 800-year-old estate, with its chapel, ruined castle, forest, farmhouses and prized vineyards, in 2003. It opened as a hotel and spa in 2009 and a 19-hole golf course followed in 2010. Now Rosewood Hotel Group has recently partnered with Ferragamo to manage the property. Take away the beautifully manicured garden beds, the heated infinity pool edged with enormous drifts of lavender and the boutique selling chic clothing and jewellery, curated by Massimo’s wife, Chiara, and you may in fact be walking down a medieval thoroughfare. Stone houses, a cobbled main street and villas set in gardens planted with rosemary to keep out the wild boar are just part of the appeal. One villa, Chiusa, for example, was formerly the town’s police station.

Meanwhile, the ruins of the castle tower overlook the village and the Church of San Michele Arcangelo, which has a beautiful fresco by Gothic painter Pietro Lorenzetti, discovered during restoration. Next door, the former priest’s house has been turned into the hotel’s casual trattoria, Osteria La Canonica, while a grand villa nearby is now the dining room of the gastronomic Ristorante Campo del Drago, a member’s club and stylish lobby lounge. There are sweeping views from its terrace, where you can dine al fresco from a breakfast buffet to full degustation in the evening. Our one-bedroom villa sits below the castle and next door to the spa. It’s set in large gardens with a romantic wishing well, old wood-burning oven, a terrace with market umbrellas, and immaculately trimmed hedges. In the mornings, giant hares graze on the lawn. Inside, the villa is the size of a small house, with a large living and dining room furnished with plump sofas and beautiful fabrics, a good-sized kitchen and an enormous bathroom with twin-sized vanities, a deep bath and Ferragamo amenities. The attention to detail is astounding. The closets go for miles with plentiful cedar hangers, shoe trees and a shoe shine kit of real brushes in a suede pouch, hooded bathrobes and black thongs for the pool. Everything is finely crafted with leather or suede; even the safe is covered in leather. A person could move right in, and some do stay for the summer.

For our first meal, in the trattoria sitting on the terrace overlooking the valley, it’s superb comfort food: a starter of bresaola, followed by thick pici pasta with beef ragu and mushrooms, and crispy salmon with zucchini slivers and mashed potatoes, washed down with the Castiglion Del Bosco on-site winery’s premium Millecento brunello 2008. Much of the hotel’s produce comes from the carefully tended kitchen garden, which can be visited via a gate near the church and is fertilised with the ash from the wood-burning ovens. It’s flourishing in summer with rotated crops of all the Italian staples, from zucchini (three types) and artichoke to the more exotic cavolo nero. Blackberry plants climb up the ancient walls, wild strawberries ramble in the beds and there’s an orchard of apricot, fig, peach and cherry trees. The hotel’s charming young chefs lead the private or group cookery lessons available at the La Canonica Cooking School, held in the beautiful upstairs kitchen and dining room of the former priest’s house, where the rope that rings the chapel’s bell hangs. I’m keen to learn how to make pasta, so I don a monogrammed apron and get stuck into mixing the eggs and durum flour, learning how to get the right texture by folding the dough in three each time before it runs through the pasta machine. It needs to be thin enough so you can see your fingernails through it. My revelation is in the sauce. The chef has me help him finely chop the white onions, then cut three different kinds of tomatoes into small pieces and salt them (always before placing them in the oil). This is all gently cooked off with bruised basil leaves. Meanwhile, a ragu involves slowly cooking finely chopped celery, carrot and onion in oil, then adding three kinds of mince: beef, veal and pork. The meat is broken up, a good slurp of red wine is added, it’s all cooked down and the tomato sauce is added, then cooked for a few minutes more. “Where is the garlic?” I ask. “There is no garlic in Tuscan cooking when onions are used”, is the answer. It’s either one or the other. I finish with a lesson in making biscotti dipped in warm Marsala sabayon. I get to keep the apron and recipes, but the best thing is sitting down to dine on it all.

Over at Ristorante Campo del Drago, named for the brunello vintage from the finest vineyard in the area, chef Enrico Figliuolo creates seasonal menus made with local produce and some tasty ring-ins, such as lobster, which flavours a luscious pasta. Drinking some of the Campo del Drago sangiovese seems mandatory, no? The desserts are also incredible: tiramisu with coffee ice cream and thick hot chocolate. A chocolate trolley follows the cheese trolley, cementing my love of this place. The next day, we tour the vineyards with manager Sabine, who explains the different qualities of the various plots of land. The grapes are all picked by hand, as the weight of the tractor adversely affects the soil and vine roots. The region of Montalcino encompasses 24,000 hectares of which 3,600 are vineyards, where the brown-red brunello has been produced since the 14th century. It was once a rare and highly prized wine, but since the region was granted Denominazione di Origine Controllata (DOC) status in the 1960s, the number of small producers has now grown to more than 200. The Castiglion del Bosco’s flawless cellar door, planted all around with white roses and herbs in tubs, is a handsome building, where you can also tour the wine vats and sit down to a guided tasting of several vintages. If you have the wherewithal, there’s also an invitation-only Wine Club featuring its own plush, rotund cellar where members’ vintages are held in specially designed refrigerated cabinets. In addition to culinary adventures, Castiglion del Bosco offers extraordinary activities, including night safaris, archery, astronomy, landscape painting, tennis and golf lessons, horseback riding, photography, Italian classes, mountain hiking and fishing. Children are welcome, too; there’s even a kid’s club and we run into a gang of happy children playing tag in the street. Other guests during our stay include a Korean pop star, a Chinese department store billionaire and the actor Ben Stiller, who is accommodated in privacy in one of the nine restored farmhouse villas tucked in the vineyards. When it’s time to leave and hit those white roads again, we find our car has been cleaned of dust and there’s a farewell gift of housemade sticky fruit gels inside. It’s this thoughtfulness, above all else, that makes the Castle in the Woods so enchanting.