Castiglion del Bosco, Tuscany

By Alison Root

Set amidst glorious Tuscan scenery is an elegant estate that blends culture and lifestyle beautifully, and there’s a golf course too! 

There are always things that we aspire to do, or places that we would like to visit given the opportunity to do so. As golfers this could be a reduction in our handicap or a trip to Augusta to watch the Masters. We might never achieve either - my handicap hasn’t reduced for a while and I’ve never been to the Masters - but we can all live in hope!

However, I was very fortunate to join a group trip to Castiglion del Bosco, one of Tuscany’s largest private estates at the heart of the Brunello di Montalcino winemaking region. Without doubt, this gem falls into the aspirational category.

For us it was not the easiest place to get to as from Rome Airport the transfer time is approximately three hours, although from Florence, it’s an hour and a half, and from Siena, under 45 minutes, so it’s worth combining a city break. The final 11km is along a bumpy unmade road so I did look a little green around the gills when I arrived!

But that was quickly forgotten because as soon as I entered this tranquil retreat that overlooks woods, vineyards and olive groves, there was no other place in the world that I’d rather be. 

Massimo Ferragamo, the youngest son of the late fashion mogul Salvatore, and his wife Chiara own this centuries-old stone-built estate and with natural Italian flair, they have done an amazing job in preserving and also bringing back to life a rustic village (the Borgo) that was once an important farming and social hub. Overlooking the beautiful Tuscan countryside bordering a cobblestoned street is a cluster of buildings including a quaint medieval church, 23 suites, two restaurants, a spa, an outdoor swimming pool, a kitchen school, and all set against the backdrop of the ruins of a Medieval castle perched on the hilltop.


Four chaps and myself (I’m a lucky girl!) had the pleasure of staying in one of 10 villas dotted around the landscape. Wow! These former farmhouses are now luxurious homes, full of rustic charm and decorated with antique furniture and artisanal pieces. With five double bedrooms, each with a separate dressing room and spacious bathroom, our villa slept 10 comfortably. But it’s the extras and attention to detail that set it apart. For example, one dressing gown is usually sufficient but here there are two - one towelling and one linen. There are also silk coat hangers, flip-flops as well as slippers, a variety of Ferragamo branded Tuscan Soul toiletries, and in the hallway there’s a selection of sunhats. I cannot say it’s like home from home as this is better!


As if by magic and with discreet sevice, each morning the kitchen centre unit was laden with fresh fruit, bread and pastries, and the wine consumed the previous evening had been re-stocked! The villa’s terrace that overlooks the 17th fairway is the ideal place to enjoy breakfast, and that’s before or after you’ve taken a swim in the salt water heated swimming pool – just a suggestion!

Italy is renowned for wonderful food and wine and this is a place to celebrate both. Whilst staying in one of the villas, guests have the option to hire a private chef, cater for themselves, dine within the estate, or take a taxi and explore the local region. 

Given that Castiglion del Bosco has its own winery that offers excellent wine- tasting sessions, and an extensive kitchen garden, it’s unlikely that you’ll want to wander too far. The two restaurants at the Borgo are very different - Campo del Drago, where you can also take breakfast, is more intimate and offers a more elaborate dining experience. We were spoilt with a taster menu that included a host of seafood dishes, traditional thin spaghetti, and although my sides were bursting, how can you resist an authentic portion of tiramisu! Osteria La Canonia is more informal, it’s a typical Tuscan trattoria with a lovely veranda overlooking the valley, and provides the ideal atmosphere to overindulge on the delicious bread and a speciality truffle pizza.

Golf Courses

No mention of golf yet and that’s because the overriding impression of Castiglion del Bosco is the lifestyle it offers with complete sun and sanctuary in the most beautiful surroundings. It just so happens that there’s a championship Tom Weiskopf-designed golf course here as well. Membership is €45,000 and the club restricts play to members, their families and estate guests, so this course gives true meaning to the words ‘millionaire’s golf’ - you won’t get stuck behind a fourball here!

The beautifully manicured course winds its way around the natural contours of the Vale d’Orcia landscape, so it’s pretty hilly and not a course to walk. There are a good variety of holes with blind shots and doglegs thrown into the mix and the many bunkers protecting the greens can be a real nuisance. From the back tees, at 685 yards, the signature 13th hole is the longest in Europe, although at 547 yards from the red tees, it was long for me too! The views are most spectacular from the 9th and 18th holes and clever Mr Weiskopf ensured a view of the Borgo from wherever you are on the course. There’s also a 19th hole with a difference that adds a bit of fun to the end of a round. It’s a 109-yard par-3 called Brunello after the most representative wine of the estate and anyone who scores a hole-in-one will be awarded €2,500 worth of wine via membership of the wine club.


When I was given the choice of either another round of golf or a spa treatment, despite the lure and attraction of this splendid course, for me the decision was a no brainer. So rather than stressing over missed putts, I knew that a full Tuscan body massage would give me a far greater sense of wellbeing - and I wasn’t wrong!

Sadly all good things have to come to an end and while Castiglion del Bosco does come at a price, it is a special place and I shall aspire to return.

For more information visit 

newsletter icon

Sign-up to receive our
Women & Golf newsletter!


Ping Womens Fourball 2020

We are using cookies to give you the best experience on our site. Cookies are files stored in your browser and are used by most websites to help personalise your web experience.
By continuing to use our website without changing the settings, you are agreeing to our use of cookies.