As autumn gently takes hold in Tuscany, the landscape takes on a golden glow. Vineyards turn russet, the air grows cooler, and the hills of the Val d’Orcia seem to invite long days of leisure punctuated by fine food, fine wine and, for a select few at least, fine golf. It’s within this idyllic setting, on the storied grounds of Castiglion del Bosco, that the Rosewood CdB Golf Cup will unfold from 3 to 5 October 2025 – a hotly contested amateur tournament set among the most visually arresting environment imaginable.
Castiglion del Bosco is no ordinary resort. Once a medieval village, or 'Borgo', it was lovingly reimagined by Massimo Ferragamo into one of Italy’s most exclusive destinations. Today, its legacy continues under new custodianship, as the property has been taken forward by visionary owners who honour its heritage while ushering in a new chapter.
Guests are welcomed into suites that combine centuries-old architecture with understated modern luxury, where terracotta tiles and wooden beams meet soft linens and private terraces overlooking the rolling countryside. Each morning begins with breakfast in the Tuscan light, accompanied by views across the UNESCO-protected Val d’Orcia.
Steve Carr
Steve Carr
The centrepiece of the weekend is play at The Club at Castiglion del Bosco – Italy’s only private members’ golf club, with outside play restricted to but a handful of resort guests. To step onto this course, designed by the late Tom Weiskopf, is to encounter Tuscany from a wholly different perspective. The fairways wind through oak forests, past ancient farmhouses and across valleys where mist lingers until late morning and shadows creep ever-larger at dusk.
It’s a course that balances risk and reward, with wide fairways playing into clever strategic green complexes that freely dispense bogeys as much as birdies. However, the real magic extends beyond the layout itself to the drop-dead gorgeous views that frame each hole. You may think it hyperbole to say there are times where it feels like the landscape is lifted directly from a Renaissance painting, but until you experience this truly unique setting, you simply won’t understand the majesty of this marvellous golfing property.
There are times where it feels like the landscape is lifted directly from a Renaissance painting
For many, it is a privilege in itself – access to The Club at Castiglion del Bosco is usually reserved for members and their guests, alongside a handful of visitors to the resort – but for one weekend only, Castiglion del Bosco is throwing open its doors for an amateur tournament quite unlike any we have seen before, with a prize that is sure to raise eyebrows.
Across 36 holes of competition play, participants will duke it out for the chance to win a series of exceptional prizes. Winners can extend the adventure far beyond Tuscany. Those who triumph will earn a golfing journey to the other side of the world, with exclusive experiences at Rosewood Kauri Cliffs and Rosewood Cape Kidnappers in New Zealand – both destinations where golf and wild landscapes converge in breathtaking harmony. Second and third place winners can enjoy Brunello di Montalcino from the estate’s award-winning vineyard and luxury golf goods from the pro shop.
Yet, as much as golf sets the rhythm, the spirit of the Rosewood CdB Golf Cup lies in Tuscan hospitality. When the day’s play is done, participants will gather at the Clubhouse, perched high above the valley. There, as the sun sinks into the hills, the atmosphere shifts from rivalry to celebration. On Saturday evening, the prize-giving dinner will unfold in true Italian style – a four-course feast that showcases the estate’s own produce, paired with Brunello di Montalcino wines crafted from vineyards visible from the tables. No doubt it'll be an evening for the books and, hopefully, the founding of a new tradition. The Rosewood CdB Cup will return in 2026 with the promise of even bigger and bolder prizes, but with a larger band of merry golfers, attracted by the siren-like call of Castiglion del Bosco's rolling fairways.
From private suite accommodation and daily breakfasts to golf carts, rental equipment and access to the Club’s exceptional practice facilities, every detail of the weekend has been thought through with care. But what makes the Rosewood CdB Golf Cup truly extraordinary is its setting: a celebration of sport, culture and community in one of Italy’s most cherished landscapes.
For those who take part, the event promises not just a tournament, but a memory – of crisp October air, rolling fairways, and a glass of Brunello raised to la dolce vita.
For more information, see rosewoodhotels.com
