Perhaps surprisingly, there aren’t many truly uber-exclusive golf clubs. There’s Augusta National, home of the Masters and otherwise inaccessible to all but its 300-odd members and their guests. Cypress Point, Burning Tree or Pine Valley Golf Club, all in the US, could be added to the list, as could JCB Golf and Country Club in the UK. All private, all invite-only – all closed to pay-and-play golfers.
In Italy, until recently, there was only one that followed the same model. Tuscany’s Castiglion del Bosco was designed by the late and venerated course architect Tom Weiskopf and opened in 2011 in the UNESCO-protected Val d’Orcia, and for years it was only playable by members.
While the prestige this brought the club was clear, adopting the Augusta model didn’t quite add up. Not simply because in Italy golf is less popular than water polo and knitting (no joke), but because the course was on the same estate as one of the world’s finest luxury hotels, and a vineyard producing some of the most highly rated of the region’s Brunello di Montalcino wines.
If it seems natural that a stay-and-play package for hotel guests might have been a success, it was not a policy the club entertained. Perhaps unsurprisingly, member numbers never got going, and the course was almost always empty.
But then recently, change. In 2022, Massimo and Chiara Ferragamo — the scions of the Ferragamo luxury empire who 20 years earlier had lovingly transformed the abandoned borgo into what has since become a three-Michelin-Key Rosewood hotel — sold the site to an undisclosed buyer for a reported €400 million.
After taking advice, the new owner decided to open up the course to hotel guests, stimulating the membership base which, capped at 300, would remain small, and in turn protect the original vision to offer members and their guests one of the most exclusive golf experiences on the planet.
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Alongside this, there would be a bi-annual tournament, the Rosewood CdB Golf Cup, a two-day event for members current and prospective, and hotel guests.
On your behalf, I signed up. Approaching Castiglion del Bosco from the road that leads south from Florence via Siena, there’s little sign of the “castle in the woods”. The forest that carpets the valley wraps around the hilltop hamlet, rendering it all but hidden. It’s only when passing along the dusty strada biancha – one of the white gravel tracks so typical of Tuscany – that leads into the estate that you get a first glimpse of the course.
Immediately, you can read Weiskopf’s fingerprint. The American former US Open champion was renowned for his ability to work with the natural contours of a landscape, where his peers were more likely to move heaven and earth to re-shape it. The course is undulating, wending around a creek that cuts through the valley, and most holes are made more challenging by changes in elevation.
One of UNESCO’s conditions on approving Ferragamo’s application to build a course on the estate was that it should make as little impression on the land as possible, a brief Weiskopf took so seriously he commissioned bunkers filled with an off-white sand that matched the color of those chalky Tuscan roads.
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Teeing off from the first hole on a sunny but fresh spring morning, the dew glistening on the fairways, it’s quickly evident why the course has been so well reviewed by those who have managed to play it. There are views of the valley in one direction or another from every hole, many of which pass one of the secluded private villas operated by the hotel.
This early in the season, I’m told the course is as tame as it will ever be, with rough that in high-season grows up to your knees cut back and those rolling fairways offering some give. No matter the time of year, the enormous greens remain lightening quick, a test for even accomplished golfers. The joy of the tournament is that we’re invited to stop after nine holes for lunch – washed down with a glass of easy Brunello, should the standard of play require it.
Castiglion del Bosco may not therefore be quite as exclusive as it was, but it seems the new model is working. The club says it’s now approaching 200 members and that six per cent of hotel guests take up the invitation to play the course. Annually, it now hosts around 5,000 rounds, a figure high enough to make the club profitable at last, but still sufficiently low that golfers will more or less always have the course to themselves. Bliss.
Indeed, one of my playing group, I learn later, takes the bait and signs up. Individual membership carries a €70,000 (approx. $81,000) joining fee and annual dues of €6,000 (approx. $7,000). Family memberships are €85,000 (approx. $99,000) and €7,000 (approx. $8,100) respectively. Half the current membership is from the east coast of the US. Apparently only one is Italian. What’s the Italian for plus ça change, plus c'est la même chose?
The next edition of the Rosewood CdB Golf Cup will be held 5-8 November 2026. For enquiries about memberships, golf packages and hotel stays, visit rosewoodhotels.com/en/castiglion-del-bosco or email cdelbosco@rosewoodhotels.com.
