Arezzo and Cortona: A Day Trip from Florence

Quick answer: Arezzo and Cortona are two hill towns in eastern Tuscany, about an hour and a half from Florence by road, that are usually visited together in one day. Arezzo is a small city with a Piero della Francesca fresco cycle and a sloping medieval square; Cortona is an Etruscan hilltown above the Val di Chiana with long views and a good archaeological museum.

Why these two, and why together

Most day trips from Florence go west and south — Siena, San Gimignano, Pisa. Arezzo and Cortona sit in the other direction, along the Val di Chiana, and they get a fraction of the traffic. They also complement each other: Arezzo is urban, layered, and holds one of the great fresco cycles of the Italian Renaissance; Cortona is compact, Etruscan, and made for walking slowly and looking at a view.

They are roughly thirty kilometres apart, which is what makes the pairing work. Arezzo in the morning, lunch on the way or in Cortona, the hilltown in the afternoon when the light on the Val di Chiana is at its best.

Arezzo: what to see

• The Legend of the True Cross. Piero della Francesca’s fresco cycle in the Basilica di San Francesco is the reason art historians come to Arezzo. Entry is timed and numbers per slot are limited, so it is booked ahead rather than walked into — in high season the slots go days in advance. Book through the official basilica booking service and confirm the current slot times before you plan the day around it.
• Piazza Grande. A square that slopes, ringed by buildings from four different centuries, with Vasari’s loggia along the top side. It is where the Giostra del Saracino, the town’s jousting tournament, is held twice a year.
• The Duomo. On the highest point of the town, with a small Piero della Francesca Magdalene painted directly onto the wall of the left aisle — easy to walk past, and worth stopping for.
• Casa Vasari. The house Giorgio Vasari built and decorated for himself. The painter who wrote the first history of Italian art was from Arezzo, and his own house is the least crowded thing in town.

Arezzo was also the setting for much of Roberto Benigni’s Life Is Beautiful, which visitors sometimes recognise before they recognise anything else.

Cortona: what to see

• MAEC. The museum of the Etruscan Academy, built around finds from the tombs in the plain below the town. Cortona was an Etruscan city long before it was a Tuscan one, and the museum is where that becomes concrete.
• Piazza della Repubblica. The town’s living room, with the staircase of the Palazzo Comunale used as public seating from morning to night.
• The Museo Diocesano. A small collection holding Fra Angelico’s Annunciation and work by Luca Signorelli, who was born in Cortona.
• Santa Margherita and the Girifalco fortress. At the top of the town, a steep climb rewarded with a view that runs across the Val di Chiana to Lake Trasimeno.

Getting there from Florence

By train, Arezzo is a direct run from Santa Maria Novella and the journey is comfortable. Cortona is the harder half: the station is at Camucia, in the plain, and the town sits several hundred metres above it, reached by bus or taxi. Doing both towns by public transport in one day is possible but leaves little margin: the Camucia bus is timed to the trains rather than to your afternoon, and the last useful connection back to Florence is earlier than most people assume. Check both legs on Trenitalia before committing to the train version of this day.

By car the two towns are a straightforward drive and the day becomes flexible. If you would rather not drive, our private transfer service covers this part of Tuscany, and a tailored itinerary can combine the two towns with a stop in the Val di Chiana on the way back.

When to go

Arezzo holds an antiques fair that fills Piazza Grande and the surrounding streets on the first weekend of the month — excellent if you want the market, difficult if you wanted the square empty. The Giostra del Saracino takes place twice a year and the town is busy around both dates. Cortona is quietest outside July and August; the summer festival season fills it.

Frequently asked questions

Can you visit Arezzo and Cortona in one day from Florence?

Yes, comfortably by car and tightly by train. Allow around three hours in Arezzo, including the Piero della Francesca cycle, and two to three in Cortona. Starting early matters more than moving fast.

Which is better, Arezzo or Cortona?

They answer different questions. Arezzo if you came to Tuscany for art and want a real working town; Cortona if you want a hilltown, a view and a slow afternoon. Visitors who only have time for one usually prefer Cortona for the setting and Arezzo for the paintings.

Is Cortona the town from Under the Tuscan Sun?

Yes. Frances Mayes’s book and the film that followed are set there, and the town has lived with that association ever since. It is a real Etruscan hilltown with a museum to match, not a film set.

How far is Arezzo from Florence?

Around eighty kilometres by road, southeast along the Valdarno. Cortona is roughly another thirty kilometres beyond it.

Seeing eastern Tuscany privately

If you are extending the trip in Florence itself, the Giardino di Boboli make a good contrast on a day you stay in the city. This is the part of Tuscany where a private day makes the most difference, because the two towns are not connected to each other by any convenient public route and the best hours are the early ones. We build these days around what you want to see rather than a fixed circuit — see how our private tours work, or tell us what you have in mind.