The Villas
The Chianti Collection allows guests to immerse themselves in this historic region of Italy fully, ranging from five to ten bedrooms and accommodating up to a maximum of 19 guests. Each home is located in a different region of the area and targets a different holiday preference from families to a group of friends.
Guests arrive feeling at home, with everything that can be a little hard and awkward to coordinate taken card by in advance. From grocery shopping to making sure there is enough bedding and amenities for all guests.
II Cellese
A 20-year restoration has transformed the ruins of this family-run private wine estate in Castellina into a drop-dead gorgeous villa that sleeps 19, a vision of Tuscan tradition given a cool, contemporary twist—an immersive way to experience one of Italy’s finest wine regions. The beautifully landscaped gardens and terrace overlooking Chainati’s hills and vineyard are ready for entertaining, with a wood-fired pizza oven best enjoyed under the stars.
Bedrooms: 10
Sleeps: 19
Location: Castellina, Chianti
Highlights
- A wine-tasting session at the house, led by a seasoned cellar master
- The heated indoor-outdoor pool and its accompanying spa with sauna
- Party-perfect outdoor dining space, complete with pizza oven, that seats 30
- A yoga platform in the olive, lavender and cypress-lined gardens
- A terrace overlooking Chianti’s hills and rows of vines
Villa Tavernaccia
This sun-soaked historic villa offers panoramic views of the olive, vine, and chestnut groves of the Tuscan hills. It is both a secluded family retreat and a peaceful base for exploring the Chianti wine region and nearby Florence. The eight elegantly en-suite bedrooms sleep up to 16, other rooms include refined reception rooms with views to the Apennines and surrounding countryside. Outside, guests can explore the cypress trees and umbrella pines.
Bedrooms: 8
Sleeps: 16
Location: Tavarnuzze
Highlights
- Views of the rolling Tuscan hills at every turn
- Refined interiors mixing polished antiques with theatrical stripes
- Tower room for sunset aperitivos
- Vast, beautiful grounds including woodland, ancient amphitheatre and kitchen garden
- Heated swimming pool, outdoor dining area and barbecue
- Private tennis court and clay bowl courts
Villa Pianvecchio
Sitting on a family-owned wine estate, this restored five-bedroom Tuscan farmhouse is just 3km from the medieval town of Radda in Chianti. It is perfect for multi-generational gatherings and celebrations with friends; this villa is made for people of all ages. From the living area, children’s playground, and outdoor pool, there is something for everyone. There’s also a gym and steam room for alfresco dining, a pizza oven, a barbecue and a well-stocked wine cellar.
Bedrooms: 5
Sleeps:10
Location: Radda, Chianti
Highlights
- Dreamy farmhouse on a working wine estate
- Beautiful heated outdoor pool
- Games for all ages and a children’s play area
- Outdoor kitchen and loggia-shaded dining area
- A gym and steam room
- Well-stocked wine cellar
- An hour’s drive to both Florence and Siena
Villa II Santo
This ultra-private estate is set high in a secluded spot between Florence and Siena. From the verandas, garden terraces, and infinity pool, you can see across Tuscany’s hills. Open living spaces foster connections and are designed for eating, drinking, and hanging out. The well-equipped kitchen is perfect for laid-back breakfasts and espressos before spending the day exploring the region or relaxing by the hand-tiled infinity pool.
Bedrooms: 8
Sleeps: 16
Location Chianti
Highlights
- A first-night chef-prepared feast of traditional Tuscan cooking, served along with a case of wine from a local vineyard.
- The sensational hilltop setting with sunny, rose-scented terraces that look out over the valley towards San Gimignano’s towers
- Serious design credentials and top-quality furnishings
- Outdoor kitchen and dining area complete with Fontana pizza oven
- Dreamy hand-tiled infinity pool with day beds and parasols
Villa Castiglioni
This six-bedroom villa is home on a working wine estate and has amazing views of Chiantie’s olive groves and vineyards – especially from the terrace of the tower at one end of the property as the sun sets. Perfect for friends and families 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.
Bedrooms: 6
Sleeps: 12
Locations: Radda, Chianti
Highlights
- Set on 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
What's Included
Guests staying at any of the villas will have access to 24-hour concierge service, and a range of bespoke services and experiences:
- Welcome and farewell dinners at the villa, prepared by a renowned local chef
- A personalised cooking lesson with an Italian chef, tailored to your party’s tastes
- Wine tasting at the villa or estate winery, guided by an expert from a leading vineyard
- A professional photography session capturing your holiday memories
- A case of Tuscan wine and a welcome hamper of local delicacies
- A lavish daily continental breakfast served at your preferred time
- Private airport transfers and meet-and-greet service
- Pre-arrival grocery shopping service and daily housekeeping
- Exclusive goodie bags for children and adults.
