Rosewood Castiglion del Bosco

Castiglion del Bosco is less a hotel than a working Tuscan world of its own: some two thousand hectares of UNESCO-listed Val d'Orcia landscape, assembled around an eight-hundred-year-old borgo restored by Massimo Ferragamo before Rosewood took the reins. The ruined castle keep, village church and stone farm buildings now hold suites, restaurants and a cookery school, while cypress-lined tracks roll away towards Montalcino in every direction.

Suites occupy the old village buildings with beamed ceilings, open fireplaces and deeply comfortable country interiors; a scattering of multi-bedroom villas with private pools suits families and longer stays. The estate produces its own Brunello di Montalcino, and tastings in the winery, truffle hunts, cooking classes and e-biking through the vines give the place an unusually rooted rhythm—guests tend to stay put rather than tour.

The private golf club, laid through the valley by Tom Weiskopf, remains Italy's only members-style course of its kind, and the infinity pool above the Val d'Orcia is one of Tuscany's finest viewpoints. Dining moves between refined Tuscan tasting menus and an easy osteria by the pool. Montalcino and Pienza are short drives; Florence and Rome are within two hours but feel much further away.