Villas in Arezzo, Cortona and surroundings

Cortona suits Lake Trasimeno and Umbria trips, Arezzo suits art and antiques, and Poppi suits forest walking in the Casentino. This is eastern Tuscany, on the border with Umbria, with fewer coach tours than Chianti. Most villas are in the countryside, so you will need a car.

Where

Villas: 176
From, per week: £298
Cheapest month: July
Nearest airports: Florence is the usual choice, around an hour and a quarter from Arezzo. Perugia is closer for Cortona, the Valdichiana and the Valtiberina, at around 45 minutes to an hour, but has fewer UK flights. Pisa and Bologna are both around two hours away. Flights from London take around two hours.

Where to stay in Arezzo, Cortona and surroundings

Cortona and Castiglion Fiorentino

Most of our villas in this region are around Cortona, a walled Etruscan town on a steep slope with a long view across the Valdichiana to Lake Trasimeno. Its Diocesan Museum holds Fra Angelico's Annunciation. Castiglion Fiorentino, 15 minutes north, is a smaller walled town with an everyday feel. Trasimeno's lakeside beaches are around 20 minutes away and Perugia airport about 45 minutes. Camucia below Cortona has a station.

Best for: Views over the Valdichiana and easy trips into Umbria

Not for you if: You dislike steep streets: Cortona climbs a hillside and parking is outside the walls.

Arezzo and Civitella in Val di Chiana

Arezzo has its old centre on a hill. Piero della Francesca's frescoes of the True Cross are in the church of San Francesco (book a timed slot), and the sloping Piazza Grande hosts a large antiques fair on the first weekend of each month. Civitella in Val di Chiana is a hill village on the western side. Trains reach Florence in about an hour, and Florence airport is around an hour and a quarter by car.

Best for: Art lovers and anyone who wants a proper town nearby

Not for you if: You want deep countryside: villas close to Arezzo look over the city's suburbs and main roads.

Pratovecchio, Poppi and Capolona (Casentino)

The Casentino is the upper Arno valley, closed in by forested mountains. Poppi's castle of the Counts Guidi dominates the valley, and Pratovecchio sits near the source of the Arno. The Casentino Forests national park above has the monastery and hermitage of Camaldoli, and the sanctuary of La Verna, where St Francis received the stigmata, is on a cliff to the east. Capolona is closer to Arezzo. Florence airport is about an hour and a half away.

Best for: Walkers, cooler summers and monasteries in the forest

Not for you if: You want to tour Siena and the Val d'Orcia: they are two hours or more away.

Lucignano, Foiano della Chiana and Marciano della Chiana (Valdichiana)

The Valdichiana is a broad valley of maize, sunflowers and Chianina cattle, crossed by old drainage canals with cycle paths along them. Lucignano is a small village built in rings around its church. Foiano della Chiana holds a long-running carnival in February and March, and there is a large outlet shopping centre on its edge. The A1 motorway is close, so Florence airport is around an hour and a quarter and Perugia about 45 minutes.

Best for: Families who want flat, easy cycling and shops nearby

Not for you if: You want hilltop drama all around: much of the Valdichiana is flat, drained farmland.

Sansepolcro, Anghiari, Monterchi and Caprese Michelangelo (Valtiberina)

The upper Tiber valley is Piero della Francesca country. His Resurrection hangs in Sansepolcro's civic museum, and his Madonna del Parto has its own small museum in Monterchi. Anghiari is a walled village above the plain where the battle Leonardo was commissioned to paint took place. Caprese, in the hills to the north, is Michelangelo's birthplace. Perugia airport is about an hour away, Florence around an hour and three quarters.

Best for: Piero della Francesca fans and walkers on the Umbrian border

Not for you if: You want a short airport transfer: this is the far eastern edge of Tuscany.

Terranuova Bracciolini and Laterina (upper Valdarno)

Between Arezzo and Florence, the Arno runs through a valley edged with eroded sandstone cliffs. Near Laterina, the Valle dell'Inferno reserve covers a stretch of the river, and the medieval bridge at Ponte Buriano is a short drive away. Terranuova Bracciolini is a planned town with supermarkets and services, and Montevarchi station has trains to Florence. Florence airport is around an hour by motorway.

Best for: Value and a quick motorway run to Florence

Not for you if: You want a postcard village: Terranuova is a modern town in the valley.

When to go to Arezzo, Cortona and surroundings

May, June and September are the best months for walking, sightseeing and the pool. July and August are hot in the Valdichiana and around Arezzo, though the Casentino stays noticeably cooler. Cortona is at its busiest in high summer. October brings the grape harvest and chestnut festivals in the Casentino, with lower prices but cold pools. In winter many country restaurants close for a few weeks, and the Casentino villages are very quiet.