Siena Hotels

Castello di Casole occupies a 10th century Tuscan castle, set snugly into a landscape of working farmland. Guests might start their day at the break of dawn, wildlife-spotting with a local naturalist. Or ride a horse through a network of country trails. A pack of curly-haired dogs might assist with a truffle hunt. Or none of the above: There’s no sense of urgency here, and visitors who believe in the concept of villeggiatura might spend days on end lounging at the pristine pool and unwinding at the spa, which occupies what used to be the wine cellar. All the hotel suites are well-appointed and comfortable, but the villas, in the former farmhouses that surround the central castle, are standouts.

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.