A private villa in Arezzo
The Hidden Voyage guide

Arezzo and Cortona

Eastern Tuscany: Piero della Francesca, Cortona and estates made for celebrations.

Best months
May, Jun, Sep, Oct
Ideal stay
7 nights
Fly into
FLR · PEG · PSA · FCO · BLQ
Getting around
Car essential
Our villas here
6 private villas
Why go

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

Our villas of the month · October 2026

Chosen this month by our team

Getting there

Airports and arrivals

FLR
Florence Airport (Amerigo Vespucci, Peretola)
about 1h by car to Arezzo, about 1h30 to Cortona

closest major Tuscan airport

PEG
Perugia San Francesco d'Assisi
about 45 minutes by car to Cortona

small Umbrian airport with seasonal European routes

PSA
Pisa International (Galileo Galilei)
about 1h45 by car to Arezzo

wide choice of European routes

FCO
Rome Fiumicino (Leonardo da Vinci)
about 2h15 by car to Cortona

best for intercontinental arrivals

BLQ
Bologna Guglielmo Marconi
about 2h by car to Arezzo

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.

Where to stay

Choosing your base

Arezzo
Culture lovers, shoppers

An elegant, prosperous city with medieval lanes, Renaissance churches and a famous antiques fair.

Cortona
Couples, food lovers

A steep hilltown of stone lanes and terraces overlooking the Val di Chiana and Lake Trasimeno.

Val di Chiana
Families, villa stays

A broad, fertile valley of farmhouses and villas between Arezzo, Cortona and Montepulciano.

Casentino
Walkers, nature lovers

A green upper Arno valley of castles, monasteries and forests, cool even in midsummer.

Valtiberina
Art lovers, peaceful stays

The upper Tiber valley around Anghiari and Sansepolcro, birthplace of Piero della Francesca.

Lucignano and Monte San Savino
Touring Tuscany and Umbria

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.

What to see

The highlights

01
Basilica of San Francesco, Arezzo

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.

02
Piazza Grande, Arezzo

An irregular sloping square framed by medieval houses and Vasari's Logge, setting for the Giostra del Saracino and the antiques fair.

03
Arezzo Cathedral

A Gothic cathedral on the city's highest point, home to Piero della Francesca's fresco of Mary Magdalene.

04
Cortona's Etruscan Museum (MAEC)

Housed in Palazzo Casali, it displays an extraordinary bronze Etruscan lamp and finds from the nearby tombs.

05
Fra Angelico's Annunciation, Cortona

The Museo Diocesano holds this radiant altarpiece among other early Renaissance treasures.

06
Eremo Le Celle

A Franciscan hermitage built into a ravine below Cortona, founded by Saint Francis in the early thirteenth century.

07
Sansepolcro and Monterchi

Sansepolcro's Museo Civico holds Piero's Resurrection, while Monterchi displays his tender Madonna del Parto in a museum of its own.

08
Castello dei Conti Guidi, Poppi

A beautifully preserved medieval castle dominating the Casentino valley, with a library of ancient manuscripts.

What to do

Experiences worth planning for

Piero della Francesca trail

Follow the painter's works from Arezzo to Monterchi and Sansepolcro over one unhurried day.

Antiques hunting in Arezzo

Browse hundreds of stalls on the first weekend of the month with an expert who knows the dealers.

Chianina beef masterclass

Learn about the valley's ancient white cattle and taste a perfectly grilled steak.

Casentino forests walk

Explore ancient beech and fir woods in the national park, visiting the monasteries of Camaldoli and La Verna.

Cortona wine tasting

Discover the Syrah and Sangiovese of the Cortona DOC on estates overlooking the valley.

Lake Trasimeno boat trip

Cross into Umbria to visit Isola Maggiore and its fishing village by boat.

Outdoors

Nature and walks

Foreste Casentinesi National Park

Vast beech and fir forests on the Apennine ridge, with marked trails and abundant wildlife.

Sanctuary of La Verna

A monastery on a rocky outcrop where Saint Francis is said to have received the stigmata, surrounded by ancient woods.

Hermitage of Camaldoli

An eleventh century monastic retreat deep in the forest, with a historic pharmacy.

Sentiero della Bonifica

A flat cycling and walking path along the Canale Maestro della Chiana between Arezzo and Chiusi.

Lake Trasimeno shores

Gentle lakeside walks and beaches a short drive from Cortona.

Where to stay

Private villas in Arezzo

See all 6 villas in Arezzo

At the table

Food and wine

What to eat

Bistecca di Chianina

Steak from the white Chianina cattle of the Val di Chiana, a protected IGP beef.

Pici

Hand rolled thick spaghetti, often served with duck sauce or garlic and tomato.

Tortelli di patate

Potato filled pasta, a speciality of the Casentino.

Prosciutto del Casentino

Ham from pigs raised in the valley's forests, rich and full flavoured.

Grifi all'aretina

A traditional stew of veal cheek and herbs, typical of Arezzo.

Ciaccia

A rustic local flatbread, sometimes made sweet or with cured pork at Easter.

What to drink

Cortona DOC

Best known for Syrah, which thrives in the warm valley below the town.

Valdarno di Sopra DOC

A small appellation in the upper Arno valley with a strong organic focus.

Chianti Colli Aretini DOCG

A Chianti subzone on the hills around Arezzo, producing bright, easy Sangiovese.

Beyond the villa

Day trips

Montepulciano and Pienza
about 45 minutes by car from Cortona

Renaissance hilltowns, Vino Nobile and pecorino in the Val d'Orcia.

Florence
about 1h by car or train from Arezzo

The great Renaissance city, easily reached without driving.

Siena
about 1h by car from Arezzo

Gothic palaces and Piazza del Campo.

Perugia and Assisi
about 1h by car from Cortona

Umbria's capital and the town of Saint Francis.

Lake Trasimeno
about 20 minutes by car from Cortona

Islands, castles and lakeside villages.

When to go

The year, season by season

May to June and September to October.

Spring

Green valleys, wildflowers and pleasant temperatures make April and May perfect for walking and art trails. Easter brings processions to the hilltowns.

Summer

Warm days in the valley and cool forests in the Casentino, with festivals and outdoor dinners. Cortona's elevation keeps evenings pleasant.

Autumn

Harvest, olive pressing and chestnut festivals fill the calendar. The woods of the Casentino turn spectacular shades of copper.

Winter

Quiet and authentic, with the antiques fair continuing year round. Some country restaurants close or reduce hours.

Weather month by month

3h11°Jan4h13°Feb5h16°Mar6h20°Apr8h24°May9h29°Jun10h32°Jul9h32°Aug7h27°Sep5h22°Oct3h16°Nov3h11°Dec

Bars: hours of sunshine a day. Above: average daytime high. Shaded: the best months.

Full weather table
MonthJanFebMarAprMayJunJulAugSepOctNovDec
Daytime high, °C111316202429323227221611
Night low, °C235812161819151163
Sunshine, hours a day3456891097533
Rainy days87798534691010
Dry days242124212325282724222021

Air: averages 1991 to 2020, Florence Peretola weather station. Dry days have less than 1 mm of rain.

Events through the year

June and the first Sunday in September
Giostra del Saracino, Arezzo
A medieval joust in Piazza Grande, held on a Saturday evening in June and in the afternoon of the first Sunday of September.
First Sunday of each month and the Saturday before
Fiera Antiquaria, Arezzo
Italy's oldest antiques fair, founded in 1968, fills Piazza Grande and the surrounding streets.
Early June
Giostra dell'Archidado, Cortona
A crossbow tournament with Renaissance costume and pageantry in Cortona's main square.
Mid August
Sagra della Bistecca, Cortona
A grand open air steak feast in the public gardens around Ferragosto.

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.

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Good to know

Practical tips

  1. Book the Piero della Francesca frescoes in San Francesco in advance; visits are in small timed groups.
  2. Cortona is steep and largely pedestrian; park at the lower car parks and use the escalators up to the centre.
  3. Arezzo's historic centre is a ZTL; avoid entering by car without authorisation.
  4. Accommodation and parking in Arezzo are busy during the antiques fair and the Giostra, so plan ahead.
  5. Monterchi's Madonna del Parto museum has limited opening days; check before travelling.
  6. Arezzo and Cortona apply a municipal tourist tax per person per night, collected by the property.
Questions

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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