
Destinations
Villas for rent in Radda in Chianti
Radda in Chianti is the village for anyone who builds the week around cellars and quiet, not cities. It is the highest and most inland commune of the Gallo Nero, 530 metres up on the ridge dividing the Pesa valley from the Arbia, seat of the Lega del Chianti from 1415: the Palazzo del Podestà, with coats of arms on its facade, still recalls it. Radda is one of the eleven UGAs of Chianti Classico, with cellars such as Castello di Volpaia and Montevertine, and the hamlet of Volpaia, where the fermentation vats sit inside medieval houses, is a few kilometres away. The villas are farmhouses between Volpaia, Monterinaldi and Selvole, reached by gravel roads. Tripcare gets to them from its Poggibonsi office in about 35 minutes, and the village has few shops: groceries are arranged in advance.
The stay
In Radda you sleep in farmhouses with thick stone walls, fireplaces that genuinely get lit on May and October evenings, and a pool over the vine rows. “Villa con piscina a sfioro nel cuore del Chianti”, ten beds, seven kilometres away, suits a group of friends here for the tastings; “Cavato La Volpe – Stunning Apt with Florence View”, for four, is the choice of two couples. Check-in is in person: we walk you through the gravel road, the well and the LPG boiler. The concierge books Castello di Volpaia and the other cellars of the Radda UGA, a chef dinner in the villa, the transfer from Montevarchi station or the airports, and a driver between Panzano, Gaiole and Siena, so nobody drives after the tastings.
Why Radda in Chianti
Radda is the choice for anyone who wants the most secluded Chianti Classico: higher than Castellina, further from Florence than Greve, without the traffic of the Chiantigiana. People come here for Volpaia and Montevertine, for long lunches and for the silence at night, with Siena around forty minutes away and Panzano and Gaiole within a driver’s reach. It is the village of couples and small groups who arrive in October for the harvest and happily stay on until All Saints; at 500 metres the summer is cooler than in the Valdelsa, and in May the evenings call for a jumper.
Getting there
Radda is reached along the SR 429 climbing from Poggibonsi and Castellina, or from Greve by way of Panzano and Lucarelli. Florence airport is about 69 minutes away by car, Pisa about 105. The nearest station is Montevarchi–Terranuova, 28 minutes of bends away, on the Florence–Arezzo line. The historic centre is a ZTL and cars stay in the car parks outside the walls; the villas are in the countryside and are not affected. Tripcare arranges the transfer from Montevarchi station and from the airports, with the time agreed before you arrive.
Villas in and around Radda in Chianti
Houses managed directly by Tripcare within fifteen kilometres, with in-person check-in.
Casino di Vescine8 guests · 1.8 km from the centre
Autentica Villa Toscana8 guests · 6.2 km from the centre
Villa nel Cuore del Chianti10 guests · 7.3 km from the centre
Solaria di Santa Maddalena16 guests · 9.7 km from the centre
Cavato — Il Capriolo4 guests · 12 km from the centre
Casa Moderna a Tenuta di Arceno6 guests · 14.5 km from the centre
Experiences in the area
Nearby events
- Chianti Classico Exposecond weekend of September
- L’Eroicafirst Sunday of October
Frequently asked questions about Radda in Chianti
Can I stay in a villa in Radda in Chianti without a car?
Only with careful planning. The villas sit on gravel roads and Montevarchi station is 28 minutes away; we take you from the station to the house and fix a driver for tasting days, so having no car becomes an advantage after the second glass. Groceries reach the villa before you do.
Which wineries can I visit in a single day from a villa in Radda in Chianti?
The right pace is two cellars a day with a long lunch in between. Castello di Volpaia and Montevertine are within the Radda UGA, a few kilometres away; Panzano with the Conca d’Oro and Gaiole make a chauffeured day out. The concierge books the visits, which at the smaller estates happen by appointment only.
Where do I buy groceries for a villa in Radda in Chianti?
The village has a few small food shops and the proper supermarkets are in Poggibonsi, about 35 minutes away. That is why in Radda groceries are arranged beforehand: the concierge has them delivered to the villa on arrival day and, if you wish, books a chef who cooks with what he brings from the market.
Do you own a villa in Radda in Chianti?
Tripcare manages it with the same team that welcomes the guests: free survey and assessment, written proposal within 48 hours.


