Destinations
Villas for rent in Castellina in Chianti
Castellina in Chianti is the village to choose if you want Chianti Classico and, with it, the freedom to roam: it sits on the Chiantigiana, the SR 222, halfway between Florence and Siena, and is one of the historic communes of the Gallo Nero. The village is small, just over 2,800 inhabitants, with the fourteenth-century Rocca housing the Archaeological Museum of the Sienese Chianti, the covered via delle Volte running along the walls and, just outside, the Etruscan tumulus of Montecalvario. Below the village, towards Fonterutoli, the vineyards of Castello di Fonterutoli run down to the Siena road. The villas stand on the hills towards Fonterutoli and Radda, at the end of gravel roads, with a view that lights up over the vine rows in the evening. Tripcare reaches them from its Poggibonsi office in just over twenty minutes.
The stay
The villas of Castellina are stone farmhouses with a pool, often infinity-edge, at the end of a gravel road we describe before arrival, because the gravel is part of the place. “Villa con piscina a sfioro nel cuore del Chianti”, ten beds, is the house for a group of friends who dine outside facing the vineyards; “Cavato La Volpe – Stunning Apt with Florence View”, for four, suits a couple with two children. Check-in is in person, with someone who knows the well, the boiler and the gate. The concierge books the cellars of Castellina and Fonterutoli, a chef dinner in the villa, transfers from Florence and Siena, and chauffeured days along the Chiantigiana towards Radda and Greve, so nobody drives after a tasting.
Why Castellina in Chianti
Castellina is the Chianti commune best placed for anyone who wants to move around: the SR 222 and the SR 429 cross here, Siena is twenty kilometres away, Florence forty-five, San Gimignano half an hour and Poggibonsi with its services a quarter of an hour. Radda is higher and more isolated, Greve closer to Florence but busier. Choose Castellina if wine is the reason for the trip but not the only plan: couples and families come from May to October, with the peak in September, when the harvest fills the cellars and the Chiantigiana smells of fermenting must.
Getting there
Florence airport is about 61 minutes away by car, Pisa about 101; from both you take the Florence–Siena motorway link as far as Poggibonsi and then the SR 429 climbing to Castellina. The nearest station is Poggibonsi–San Gimignano, on the Empoli–Siena line, 23 minutes from the village. The historic centre is a ZTL: you park outside the walls and walk in, but the villas are in the countryside and are not affected. Tripcare arranges a private transfer from the airports and the station, with the time agreed before you arrive.
Villas in and around Castellina in Chianti
Houses managed directly by Tripcare within fifteen kilometres, with in-person check-in.
Experiences in the area
Nearby events
- Palio di Siena2 July and 16 August
- Chianti Classico Exposecond weekend of September
- L’Eroicafirst Sunday of October
Frequently asked questions about Castellina in Chianti
Can I visit Siena and Florence on the same day from Castellina in Chianti?
Better on two separate days. Siena is twenty kilometres away: a morning there and back for the pool. Florence is forty-five kilometres along the Chiantigiana or the motorway link and deserves a full day. The concierge books timed tickets for Siena cathedral and the Uffizi and, if you prefer, a driver for both days.
Can I walk to the wineries of Castellina in Chianti from the villa?
From the village, yes: some cellars have their tasting room in the centre and Fonterutoli is a stroll from its own hamlet. The villas, though, sit on the hills a few kilometres of gravel road away, so estate visits call for a car or a driver. The concierge books tastings in Castellina and Fonterutoli and a driver for the way back.
Do I need a car for a villa holiday in Castellina in Chianti?
Yes. The villas sit at the end of gravel roads, the nearest station is Poggibonsi, 23 minutes away, and the supermarket is in Poggibonsi or in Castellina itself. If you would rather not drive, we arrange the transfer on arrival and departure and chauffeured days for wineries, Siena and San Gimignano, so the holiday works without a hire car.
Do you own a villa in Castellina in Chianti?
Tripcare manages it with the same team that welcomes the guests: free survey and assessment, written proposal within 48 hours.