Country road SP103 is a far cry from the multi-lane SR2 from Rome. Once you exit the freeway heading towards Tuscany, turbocharged supercars “cruising” at well over 100 mph give way to a quiet that separates the countryside from the hustle of Italy’s capital. Two hours away, and you might as well be on a different planet.

The resort offers great vantage of the surrounding hills

As you leave the smooth tarmac of the highway, you’ll test the real mettle of your ride on the bumpy trails leading up to Castiglion del Bosco, a historic hamlet on the southern fringe of Tuscany dating back to 100 A.D. The SP103 winds its way up a hill, framed by Mediterranean cypress trees known to have been planted to lead pilgrims to Rome. After about 45 minutes, the road opens up and the seemingly modest reception of the Rosewood Castiglion del Bosco sends out a concierge to take welcome you.

It is then you will realise that this is no ordinary five-star resort.

Il Borgo Avenue

Since 2023, Massimo and Chiara Ferragamo have transformed this quiet Italian enclave into one of the most premium resorts in the world. The Rosewood Castiglion del Bosco is currently ranked No.1 by T + L magazine (100 Best Hotels in the World), and with its private golf club, is surely one of the most exclusive places on the planet to play the game. The entire 2,000-hectare estate offers panoramic views across the Val d’Orcia, and many of the Rosewood’s 42 suites share this vantage. Bathed in the warm glow of a Tuscan dusk, the ambience encourages a prolonged stare into the beyond if only to soak in the magic of the moment.

In addition to the suites, Rosewood Castiglion del Bosco also offers 11 unique luxury Tuscan villas, each created from restored Tuscan farmhouses from the 17th and 18th century.

For a small fortune, these private homes offer elements from the lives of the rich and famous, replete with heated pools, terraces, several bedrooms with en-suite baths,  well-appointed living areas, kitchens that would make Jamie Oliver envious, and gardens to hold your very own al fresco shindigs. Throw in the natural, untouched beauty of the Tuscan countryside and you’d never need to leave your accommodations for pleasure.

Hole 2 at Castiglion del Bosco Golf Club

But if you’ve come for the golf – and you should – then that’s a good reason to leave your lodging for a sublime experience.

Tom Weiskopf chose Castiglion del Bosco to build his only course in Continental Europe. With his passing in 2022, it will sadly remain that way. The American’s vision of maximising the natural undulation of the property provides the course with wonderful changes in elevation, incredible shot vales, and a great variety of holes.

Hole 8

“Tom loved this landscape and especially the views and long- distance vistas, which he emphasized in his design,” says David Waters, General Manager and Director of Golf at The Club at Castiglion del Bosco. “There are natural valleys to play down and ridges to play along and across, which meant very little earth movement was required during construction. Tom particularly liked the green locations, including the 17th, which is on top of a hill with a naturally beautiful backdrop, looking up to the forested hills and Medieval castle ruin. In addition to a drivable par-4, one of Tom’s design motifs, inspired by the Old Course at St Andrews. The course also has a reputation for being the best conditioned in Italy.”

Hole 9

As of now, Castiglion del Bosco is only opened to members, their guests, and those staying at the resort. “Our membership is diverse, international and, as we say, it is a club full of friends,” Waters elaborates. “What brings us together is a shared passion for golf and Tuscany. The majority of the membership is European – including from the UK, Germany, Switzerland, Belgium, The Netherlands, France, Sweden, Denmark and Italy – while approximately 40 per cent are from the United States. We also have members from Korea and South Africa.”

Even for a club as exclusive as this, Waters feels that if you’re not moving ahead, you’re likely to fall behind. “We are embarking on a multi-million-dollar course upgrade this winter, which will lengthen the course to 7,500 yards, see all bunkers renovated and further enhance the playing experience.

The golf clubhouse

The work is being overseen by golf course architect Phil Smith, long- time partner of Tom Weiskopf and collaborator on the original course design, alongside leading golf course consultancy Turfgrass, which oversaw the transformation of 2027 Ryder Cup venue Adare Manor, Ireland,” Waters reveals.

In addition, new fairway drainage will provide better conditioning all year round. Grassing lines and native grass areas will be improved, and the practice range will be upgraded with expanded tees and targets. But any improvements to the clubhouse will need to follow restrictive guidelines.

Clubhouse view

“As the club sits within a UNESCO protected landscape, as well as a locally managed reserve, planning restrictions are necessarily strict,” Waters adds. “This includes permissions only being given to develop on the footprint of previous buildings or ruins, and using local stone and building materials.

“The clubhouse, which opened in 2017, is actually a restored stable block, using individually numbered stones from the original building. We also used stone and building materials recycled from other local ruins, including stone for the patio, with new travertine stone sourced from an approved local quarry. Ultimately, the project was about carefully restoring a ruin and creating a new building that looks as if it had been in the landscape for hundreds of years yet, is, in fact, a world-class clubhouse featuring a members’ lounge, restaurant, bar, patio and wine and cigar room, with an underground golf car and equipment storage facility.”

Winery at Castiglion del Bosco ageing cellar

The course is a fun one to play. Landing areas for your drives are wide, and the rough was reasonable for a mid-handicapper to negotiate.

Still, at 7,187 yards from the back tees, Weiskopf’s course is no slouch. There is no water, but bunkers are strategically placed to make you think on nearly every shot. All around you, the scenery of the surrounding Tuscan countryside distracts you from your game to the point where you may not care about the score.

But if you do, and you’re tied with your playing partner after the finishing 18th – which, incidentally, is a brutish 449-yard par-4 where the fairway leads all balls towards a bunker – Weiskopf put in a par-3 19th hole as a tie-breaker. The club has a standing prize of a Brunello magnum for anyone getting an ace here.

Hole 19 allows golfers an opportunity to settle ties

Even if you don’t get that illusive hole-in-one, you’ll find ample opportunities to taste the best wines this famed region has to offer. The renowned town of Montalcino is just a 30-minute drive away, and there, you’ll find streets lined with wine shops where you can select from the area’s best.

Of course, you won’t even need to go that far for great wine. The estate’s own 62-hectare vineyards produce Sangiovese red wine grape varieties that are the foundation of Brunello di Montalcino wines. The Winery at Castiglion del Bosco, a short five-minute drive from the hotel, hosts tours and tastings. A visit there cannot do without a short glimpse at the beautiful private cellar where guests and members can host social events. Members of the Castiglion del Bosco Golf Club not only enjoy privileged rates at the Rosewood, and at the Winery, but they also invited to exclusive wine dinners and tastings around the world courtesy of the Millecento Wine Club.

Il Borgo La Piazzetta

Exquisite wine occasions notwithstanding, one of the most poignant events planned at Castiglion del Bosco is the Weiskopf Invitational, founded and hosted personally by the American course architect.

“He so enjoyed coming and spending the week in Tuscany with his wife Laurie,” Waters reminisces. “The members loved having them here, too, and many friendships were formed. There was great sadness when we lost Tom. A few months before he died, members sent him some sand from one of the bunkers, to remind him of Castiglion del Bosco. After his passing, Laurie returned to Tuscany with a group of members and friends from their home at the Yellowstone Club to play a match. That match will become an annual event between both clubs – and we will play for the ‘Sands of Tom’.”