Rosewood Castiglion del Bosco
Castiglion del Bosco, Montalcino
Situated in the UNESCO World Heritage Site of Val D’Orcia, this centuries-old estate south of Siena is truly incredible: Beyond the fact that you walk amidst remnants of walls from the 1100s, it’s surrounded by Brunello di Montalcino vineyards, there’s a world-class golf course, on-site truffle hunting, and the food is unbelievable. There’s a fancy restaurant, but there’s also a casual pizzeria—and kitchens in the villas where you can feast on bread and incomparably sweet tomatoes. While it's plenty romantic, they have a lot of activities (including cooking classes) for kids.