Villas in Tuscany Chianti

Greve and Castellina suit wine lovers, San Gimignano and Colle Val d'Elsa suit sightseers, and Montaione is best for golf and Pisa flights. Most villas are rural farmhouses with pools, reached by gravel roads, so you need a car. The Valdarno side, towards Arezzo, is usually better value and has trains to Florence.

Where

Villas: 541
From, per week: £329
Cheapest month: October
Nearest airports: Florence (Peretola) is closest for most of Chianti; Pisa has more UK flights and suits Montaione and the west. Bologna is around an hour and a half from northern Chianti. Flights from London take around two hours.

Where to stay in Tuscany Chianti

Greve, Panzano and San Polo (northern Chianti)

Greve in Chianti has more of our villas than any other single town in the region. Its arcaded, triangular piazza is lined with wine shops and butchers, and Panzano and the abbey at Badia a Passignano are a few minutes away. San Polo sits in quieter hills nearer Florence. Florence airport is around 45 minutes to an hour by car.

Best for: Wine tasting and the shortest drive to Florence

Not for you if: You dislike narrow bends: the Chiantigiana road through Greve is slow and twisting.

San Gimignano, Colle Val d'Elsa and Certaldo (Val d'Elsa)

This is our largest group of villas, spread around San Gimignano's towers, Colle Val d'Elsa with its crystal-glass workshops, Certaldo's hilltop old town (reached by funicular) and the villages of Casole d'Elsa, Linari and Gavignano. Poggibonsi is the practical town for supermarkets. Volterra and Siena are each around half an hour away, and Florence airport about an hour.

Best for: Sightseers who want medieval towns within a short drive

Not for you if: You want empty streets: San Gimignano is packed with day-trippers from mid-morning in summer.

Castellina, Radda, Gaiole and Castelnuovo Berardenga (Chianti Classico)

Castellina in Chianti sits on the ridge road towards Siena, about 25 minutes away. Radda is small and walled, and near Gaiole the Ricasoli family's Brolio castle sells its own wine. Castelnuovo Berardenga, further south, is closest to Siena. Restaurants in these villages are few and book up on summer evenings, and every October Gaiole hosts L'Eroica, a vintage-bike ride on the gravel roads.

Best for: Classic Chianti hills, vineyards and castles, with Siena close by

Not for you if: You want a quick airport run: Florence is over an hour and the roads are slow.

Montaione, Castelfalfi and Gambassi Terme (west of Chianti)

Strictly speaking this is the hill country between Chianti and Pisa rather than Chianti itself. Castelfalfi is a restored medieval hamlet with a golf course and resort-style holiday homes. Montaione and Gambassi Terme are quiet hill villages, and Castelfiorentino below has a station on the Florence line. Pisa airport is around an hour away, Florence around 50 minutes.

Best for: Golfers, families and anyone flying into Pisa

Not for you if: You want classic Chianti vineyards around you: this is gentler farmland further west.

San Casciano, Tavarnelle, Barberino and San Donato in Poggio (Val di Pesa)

This western edge of Chianti runs along the toll-free Florence to Siena road, which makes it the easiest base for day trips to both cities. San Casciano is barely 20 minutes from Florence's southern edge. San Donato in Poggio is a small walled village, and Montespertoli and Mercatale have wine estates in gentler hills. Florence airport is around 40 minutes away.

Best for: Easy access to Florence and the fast Florence-Siena road

Not for you if: You want total quiet: the villages near the dual carriageway hear some traffic.

Bucine, Ambra, Pergine Valdarno and Monte San Savino (Valdarno and Arezzo side)

East of the Chianti hills, these villages sit above the Arno valley. Montevarchi has a station with trains to Florence in under an hour, and Arezzo is around half an hour away. Monte San Savino is a walled hill town on the edge of the Valdichiana. Florence airport is roughly an hour by motorway.

Best for: Better value and quieter countryside on the eastern edge of Chianti

Not for you if: You want to tour Chianti's wine villages from the door: Greve and Radda are a long drive back over the hills.

When to go to Tuscany Chianti

May, June and September are the best months: warm enough for the pool, but the countryside is green and the art cities are less crowded. July and August are hot, often uncomfortably so in the afternoons, and Florence and San Gimignano are at their busiest. October brings the grape and olive harvests and cooler days, though pools may be too cold. From November to March many restaurants close for a month or two and some villas only open from Easter.