Villa Castiglioni

A former medieval watchtower converted into a six-bedroom villa on a vineyard outside Radda in Chianti.

Villa Castiglioni

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 terrace of the tower at one end of the property as the sun sets. 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. There’s plenty to keep all ages entertained, from billiards and foosball to pétanque, plus a yoga studio (on request) and hammam.

Bedrooms: 6
Sleeps: 12
Location: Radda, Chianti
7 nights from $90,000
Availability: 31 May, 14 June, 21 June, 28 June, 5 July, 12 July & 19 July 2025

Contact one of our expert Journey Designers or talk to your travel advisor to learn more and start planning.

Highlights

  • Set in the rambling grounds of a working wine estate
  • Panoramic countryside views from the billiards room and bar in the medieval tower
  • Outdoor kitchen and dining area
  • Beautiful heated outdoor pool
  • A spa treatment room, gym and hammam
  • Games room and a play area for children
  • Pétanque court
  • Around an hour’s drive to both Florence and Siena

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 (one light dinner is included as well as a daily help-yourself breakfast and a wine tasting session at the estate’s wine cellar). The outdoor pool and wellness spaces are the final stand-out touch.

The location

Of all Chianti’s quintessential Tuscan hilltop towns, Radda takes the top spot, with its medieval tangle of streets, charming old houses and 360-degree views over the surrounding vineyards and golden hills. It’s in the heart of the Chianti Classico DOC, a designation with a history that dates back more than 300 years, and some of the best wines in the world. The food is just as good, with local restaurants creating the most delicious dishes from the top-quality seasonal local produce, and in fabulous settings. Nearby, you’ll find charming Tuscan towns to explore, and it’s an hour’s drive to the must-see cities of Florence and Siena.

THE A&K GUEST EXPERIENCE: WHAT’S INCLUDED?

When you book one of our collection of Private Estates in Chianti, your stay comes with a host of additional experiences, services and treats, including:

  • A case of Tuscan wine and a welcome hamper of specialty foods from local producers, from artisan cheesemakers to homemade breads and homegrown olives.
  • Welcome and farewell dinners at the villa, prepared by a highly esteemed local chef.
  • Wine-tasting at the villa or in the winery on your estate, with an expert from one of Chianti’s leading vineyards.
  • Cookery class with a local Italian chef, who will tailor the class to suit your party’s taste and ability.
  • A session with a professional photographer, who will come to the villa to capture some special moments, for the best set of holiday photos you’ve ever had.
  • Exclusive goodie bags of gifts for children and adults.
  • A dedicated local host and concierge who will take care of every detail of your stay, with daily visits and round-the-clock availability on WhatsApp, should you need them.
  • Pre-arrival grocery shopping service.
  • An airport meet-and-greet host to whisk you through the airport to your waiting private car.
  • Private return airport transfers.
  • A beautifully presented breakfast every day, at a time to suit you.
  • Daily housekeeping.

We value your privacy

This website uses cookies to ensure you get the best experience using our website. By clicking "Accept and Continue", you consent to our use of cookies. Read More

Enquire