Castiglion del Bosco

The course was designed by Tom Weiskopf with Phil Smith, who says he worked on it with him in 2012. Weiskopf, who died in August 2022 and was inducted into the World Golf Hall of Fame in 2024, came back often: it is his only design in continental Europe. The line the club likes to quote is his: “The course looks like it has been here for a hundred years.”

The layout settles into the hills and valleys of the estate, an 800-year-old historic property at Montalcino with views over the Val d'Orcia, a UNESCO site. The club speaks of a design that “walks lightly” on the landscape, and Massimo Ferragamo has recalled the care taken in design and construction, because the course lies in a protected area.

In 2023-24 a multimillion-euro investment was completed: new back tees that stretch the course to 7,500 yards, restored bunkers with new liners, more than 135,000 metres of drainage for year-round play, drought-resistant grasses and more areas of native grass. The new targeted irrigation has cut water use by 20 per cent and, according to Phil Smith, makes Castiglion del Bosco the most sustainable course he has designed in twenty years.

After the 18th comes the 19th hole, the “Brunello Hole”: a short par 3 for members and guests, where the match is decided for a magnum of Brunello.

The Club at Castiglion del Bosco is, by its own definition, the only private golf club in Italy: membership is by invitation. Non-members can try the course in two ways. Guests of Rosewood Castiglion del Bosco can play the 18 holes by booking in advance. Other individual golfers can apply for Unaccompanied Play through the General Manager Introduced Guests programme: the request must be completed online, stating date, number of players, home club and official handicap, and play is subject to the club's confirmation.

The club does not publish a green fee list or a minimum handicap, and notes that tee times are designed to preserve members' privacy and pace of play.

Members gather for the two main events: the Weiskopf Invitational, a member & guest tournament that Weiskopf himself hosted every year in May, and the President's Cup, a weekend of golf and dinners with the estate's wines. Every autumn there is the grape harvest experience, and members have access to the winery that produces Brunello di Montalcino from 62 hectares of vineyards planted only with Sangiovese.

In December 2025 the club was ranked 55th in the Top 150 Platinum Clubs of the World 2026-27, Golf & Country Clubs category, according to the Club Leaders Forum ranking: its second consecutive appearance. Next to the course stands the Rosewood Castiglion del Bosco, with 42 suites, 11 villas and the restaurant Campo del Drago, which has two Michelin stars.

• The nineteenth hole. The Brunello Hole is played for a magnum of Brunello.
• Only one Weiskopf in Europe. The course is the architect's only continental design.
• 135,000 metres of drainage. Laid during the upgrade to allow play all year round.
• Weiskopf in person. Every May he hosted the member & guest tournament that bears his name.