

Arezzo and Cortona
Eastern Tuscany: Piero della Francesca, Cortona and estates made for celebrations.
Why choose Arezzo and Cortona
Eastern Tuscany is a land of quiet hilltowns, Renaissance painting and wide valleys that feel far from the crowds. Arezzo holds one of Italy's great fresco cycles, Piero della Francesca's Legend of the True Cross, and a sloping main square that hosts a monthly antiques fair. Cortona, high above the Val di Chiana, looks out over Lake Trasimeno and has Etruscan roots older than Rome.
This region suits travellers who enjoy art and authenticity in equal measure. The Piero della Francesca trail leads through Monterchi and Sansepolcro, the Casentino forests shelter ancient monasteries, and the Chianina cattle of the valley provide Tuscany's most famous steak. Villas here offer space and views, with Florence, Siena and Umbria all close.
Ideal for: Weddings and events, Large groups, Culture · Relaxed, art and countryside
Chosen this month by our team



Airports and arrivals
closest major Tuscan airport
small Umbrian airport with seasonal European routes
wide choice of European routes
best for intercontinental arrivals
alternative for long haul connections
- Regional trains link Florence and Arezzo in about 1h, and selected Frecciarossa and Italo services stop at Arezzo on the line between Milan and Rome.
- Camucia Cortona and Terontola stations serve Cortona, with shuttle buses or a short taxi ride up to the town.
- The A1 motorway passes through the region, with exits at Arezzo, Monte San Savino and Valdichiana.
- Private transfers and helicopter flights can be arranged from Florence or Rome.
We arrange private transfers, drivers, boats and helicopters for every villa.
Choosing your base
An elegant, prosperous city with medieval lanes, Renaissance churches and a famous antiques fair.
A steep hilltown of stone lanes and terraces overlooking the Val di Chiana and Lake Trasimeno.
A broad, fertile valley of farmhouses and villas between Arezzo, Cortona and Montepulciano.
A green upper Arno valley of castles, monasteries and forests, cool even in midsummer.
The upper Tiber valley around Anghiari and Sansepolcro, birthplace of Piero della Francesca.
Small walled towns in the western valley, close to the A1 and to Siena.
Positions are approximate: the exact address is shared once your stay is confirmed.
The highlights
Piero della Francesca's Legend of the True Cross fills the chancel with luminous, geometric scenes painted in the fifteenth century. Visits are in small groups by timed reservation.
An irregular sloping square framed by medieval houses and Vasari's Logge, setting for the Giostra del Saracino and the antiques fair.
A Gothic cathedral on the city's highest point, home to Piero della Francesca's fresco of Mary Magdalene.
Housed in Palazzo Casali, it displays an extraordinary bronze Etruscan lamp and finds from the nearby tombs.
The Museo Diocesano holds this radiant altarpiece among other early Renaissance treasures.
A Franciscan hermitage built into a ravine below Cortona, founded by Saint Francis in the early thirteenth century.
Sansepolcro's Museo Civico holds Piero's Resurrection, while Monterchi displays his tender Madonna del Parto in a museum of its own.
A beautifully preserved medieval castle dominating the Casentino valley, with a library of ancient manuscripts.
Experiences worth planning for
Follow the painter's works from Arezzo to Monterchi and Sansepolcro over one unhurried day.
Browse hundreds of stalls on the first weekend of the month with an expert who knows the dealers.
Learn about the valley's ancient white cattle and taste a perfectly grilled steak.
Explore ancient beech and fir woods in the national park, visiting the monasteries of Camaldoli and La Verna.
Discover the Syrah and Sangiovese of the Cortona DOC on estates overlooking the valley.
Cross into Umbria to visit Isola Maggiore and its fishing village by boat.
Nature and walks
Vast beech and fir forests on the Apennine ridge, with marked trails and abundant wildlife.
A monastery on a rocky outcrop where Saint Francis is said to have received the stigmata, surrounded by ancient woods.
An eleventh century monastic retreat deep in the forest, with a historic pharmacy.
A flat cycling and walking path along the Canale Maestro della Chiana between Arezzo and Chiusi.
Gentle lakeside walks and beaches a short drive from Cortona.
Private villas in Arezzo
Food and wine
What to eat
Steak from the white Chianina cattle of the Val di Chiana, a protected IGP beef.
Hand rolled thick spaghetti, often served with duck sauce or garlic and tomato.
Potato filled pasta, a speciality of the Casentino.
Ham from pigs raised in the valley's forests, rich and full flavoured.
A traditional stew of veal cheek and herbs, typical of Arezzo.
A rustic local flatbread, sometimes made sweet or with cured pork at Easter.
What to drink
Best known for Syrah, which thrives in the warm valley below the town.
A small appellation in the upper Arno valley with a strong organic focus.
A Chianti subzone on the hills around Arezzo, producing bright, easy Sangiovese.
Day trips
Renaissance hilltowns, Vino Nobile and pecorino in the Val d'Orcia.
The great Renaissance city, easily reached without driving.
Gothic palaces and Piazza del Campo.
Umbria's capital and the town of Saint Francis.
Islands, castles and lakeside villages.
The year, season by season
May to June and September to October.
Green valleys, wildflowers and pleasant temperatures make April and May perfect for walking and art trails. Easter brings processions to the hilltowns.
Warm days in the valley and cool forests in the Casentino, with festivals and outdoor dinners. Cortona's elevation keeps evenings pleasant.
Harvest, olive pressing and chestnut festivals fill the calendar. The woods of the Casentino turn spectacular shades of copper.
Quiet and authentic, with the antiques fair continuing year round. Some country restaurants close or reduce hours.
Weather month by month
Bars: hours of sunshine a day. Above: average daytime high. Shaded: the best months.
Full weather table
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Daytime high, °C | 11 | 13 | 16 | 20 | 24 | 29 | 32 | 32 | 27 | 22 | 16 | 11 |
| Night low, °C | 2 | 3 | 5 | 8 | 12 | 16 | 18 | 19 | 15 | 11 | 6 | 3 |
| Sunshine, hours a day | 3 | 4 | 5 | 6 | 8 | 9 | 10 | 9 | 7 | 5 | 3 | 3 |
| Rainy days | 8 | 7 | 7 | 9 | 8 | 5 | 3 | 4 | 6 | 9 | 10 | 10 |
| Dry days | 24 | 21 | 24 | 21 | 23 | 25 | 28 | 27 | 24 | 22 | 20 | 21 |
Air: averages 1991 to 2020, Florence Peretola weather station. Dry days have less than 1 mm of rain.
Events through the year
Planning Arezzo and Cortona?
Tell us your dates and the group: we reply with availability and the full price, usually within one working day, and arrange transfers, chefs and boats.
Practical tips
- Book the Piero della Francesca frescoes in San Francesco in advance; visits are in small timed groups.
- Cortona is steep and largely pedestrian; park at the lower car parks and use the escalators up to the centre.
- Arezzo's historic centre is a ZTL; avoid entering by car without authorisation.
- Accommodation and parking in Arezzo are busy during the antiques fair and the Giostra, so plan ahead.
- Monterchi's Madonna del Parto museum has limited opening days; check before travelling.
- Arezzo and Cortona apply a municipal tourist tax per person per night, collected by the property.
Arezzo and Cortona: frequently asked
Is Cortona worth visiting?
Yes: it combines Etruscan heritage, Renaissance art, excellent food and sweeping views over the Val di Chiana and Lake Trasimeno. It is also a convenient base for Umbria and southern Tuscany.
What is Arezzo famous for?
Piero della Francesca's frescoes, the Giostra del Saracino, its monthly antiques fair and a long tradition of goldsmithing. The city is also the setting of several scenes from the film Life is Beautiful.
How do you get from Florence to Arezzo?
Regional trains take about 1h, and the drive along the A1 takes a similar time. Some high speed trains also stop at Arezzo.
When is the Arezzo antiques fair?
It is held every first Sunday of the month and the preceding Saturday, in and around Piazza Grande.
Which airport is closest to Cortona?
Perugia (PEG) is about 45 minutes away. Florence (FLR) is about 1h30 and Rome Fiumicino (FCO) about 2h15.
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