Castiglion del Bosco Golf Club

Few golf courses in the world sit inside a UNESCO World Heritage Site, but Castiglion del Bosco does. The estate dates to medieval times — a Sienese fortress that later became one of Tuscany's most storied wine properties — and the golf course, designed by Tom Weiskopf and opened in 2004, was shaped around it with unusual sensitivity. Weiskopf routed the layout through ancient oak forests and across the open Crete Senesi countryside, respecting the land's centuries-old character rather than imposing upon it. The result is a course that feels less built than revealed.

Montalcino is the home of Brunello, arguably Italy's most celebrated red wine, and the Castiglion del Bosco estate produces its own. The broader Val d'Orcia landscape — rolling golden hills, cypress-lined roads, stone farmhouses — is among the most painterly in Europe, and it defines the backdrop for nearly every hole.

Access is restricted to residents and members of this ultra-private Ferragamo family resort, which keeps the course uncrowded and immaculate. Golf here is inseparable from the wider experience of the estate — the food, the wine, the silence.