7-Nights Villa Castiglioni - Private Estate Collection from $65,000

Set on a working wine estate, a couple of miles from the medieval hilltop town of Radda, this six-bedroom villa has sensational views of Chianti’s olive groves and vineyards — especially from the former medieval watchtower at one end of the property. It’s ideal for families and friends travelling together, with several terraces for outdoor dining, including one overlooking the pool and children’s play area beyond.

The Villa
Owned by the Austrian family behind the Tenuta di Carleone winery which has been producing Sangiovese wine for over a decade, this six-bedroom villa is surrounded by olive trees, vineyards and rolling hills. The glorious rural landscape is typically Tuscan and so too is Villa Castiglioni’s stone building, terracotta-tiled roof and medieval tower that has been turned into a billiards room and bar. Inside, contemporary furniture, bold abstract art and flashes of colour (geometric cushions, cosy rugs, painted sea-green wardrobes) are juxtaposed with exposed stone walls, beamed ceilings and wooden floors. The accommodation is split between two buildings. The ‘Owner’s Wing’ has a kitchen and conservatory, along with a dining room, drawing room, a TV area with a fireplace, and a library; on the first floor are two lovely bedrooms. The Guest Wing has another four bedrooms, all ensuite, split between the main floor – which has a pair of sitting rooms, two dining rooms and a fully-equipped kitchen made by artisan kitchen-makers in Florence – and the lower garden level. For chilly evenings, there is underfloor heating and a fireplace; for balmy summer nights, a wood-fired pizza oven, barbecue and multiple terraces for supper outdoors. The outdoor pool and wellness spaces are the final stand-out touch.