Etruscan roots, Renaissance masterpieces & Italy's greatest antique fair — stay green in eastern Tuscany
Arezzo is one of the oldest continuously inhabited cities in Italy, its roots reaching back to the Etruscan civilisation that flourished here well before Rome rose to power. The city sat at the crossroads of four river valleys — the Arno, the Val di Chiana, the Casentino, and the Val Tiberina — making it a strategic trading hub for millennia. That layered history is still visible in every stone: an Etruscan wall fragment here, a Roman amphitheatre there, a medieval tower beside a Renaissance loggia.
For art lovers, Arezzo is a pilgrimage. The Basilica di San Francesco houses Piero della Francesca's fresco cycle The Legend of the True Cross (c. 1452–1466), widely regarded as one of the supreme achievements of Italian Renaissance painting. Just across town, the Church of San Domenico holds a monumental painted crucifix by Cimabue, Giotto's teacher and the artist who first broke with the flat Byzantine tradition.
Cinema fans will recognise Piazza Grande and the surrounding streets as the filming location for Roberto Benigni's La Vita è Bella (Life is Beautiful, 1997), which won three Academy Awards. Every corner of the old town seems to carry a trace of that gentle, heartbreaking film.
Then there is the Fiera Antiquaria — Italy's oldest and largest antique fair, held on the first Sunday of every month since 1968. Over 500 dealers fill Piazza Grande and the surrounding lanes with furniture, prints, ceramics, jewellery, and curiosities. It is the single best reason to plan a weekend in Arezzo, and it draws collectors from across Europe.
Unlike Florence or Siena, Arezzo has not been overwhelmed by mass tourism. Prices are lower, restaurants cook for locals, and you can walk the centro storico in the golden evening light without jostling for space. It is authentic Tuscany — the kind travellers dream about.
Arezzo is superbly connected by rail. The city sits on the main Rome–Florence line, with direct Trenitalia services reaching Florence Santa Maria Novella in about an hour and Rome Termini in roughly 90 minutes on the fast trains. Arezzo station is a flat 10-minute walk south of Piazza Grande — no bus needed.
If you are arriving by car, the A1/E35 autostrada passes just west of the city. Parking is available at the Parcheggio Pietri below the Fortezza Medicea (a moving stairway connects it to the hilltop old town) or along Viale Giotto. Driving within the centro storico is restricted by a ZTL (zona traffico limitato), so check your hotel's permit status before entering.
The old town is compact enough to explore entirely on foot, but give yourself at least two full days. Spend the first morning with Piero della Francesca in the Basilica di San Francesco — tickets should be booked in advance — then wander through Piazza Grande, the Logge del Vasari, and up to the Fortezza Medicea for panoramic views across the Val di Chiana. The second day works well for the Cathedral and the Roman amphitheatre-museum, followed by lunch in the San Marco quarter.
Arezzo is also an ideal base for day trips into eastern Tuscany. Cortona is just 30 km south — a hilltop town overlooking Lake Trasimeno, made famous by Under the Tuscan Sun. Sansepolcro, 40 km northeast, is the birthplace of Piero della Francesca and home to his extraordinary Resurrection fresco in the Museo Civico. The medieval walled village of Anghiari, 30 km away, sits above the upper Tiber valley and was the site of the 1440 battle famously depicted (and lost) by Leonardo da Vinci. Siena is 75 km west, and Florence 80 km northwest — both reachable comfortably by train or car.
The historic heart of Arezzo climbs the hillside from the cathedral down to Piazza Grande. Staying here places you within steps of Piero della Francesca's frescoes, the antique fair, the Logge del Vasari, and the best restaurants. Boutique hotels and B&Bs occupy converted medieval and Renaissance buildings. It is the most atmospheric base, though streets are narrow and car access is limited.
The streets between the train station and the old town — particularly along Viale Giotto and Via Guido Monaco — offer practical mid-range hotels with easy access to both the railway and the centro storico. This is a strong choice if you are arriving by train and want a no-fuss base with modern amenities.
East of the cathedral, the quieter San Marco neighbourhood clusters around the church of the same name. It is still within the old walls, but feels more residential and less tourist-focused. Several trattorias here cater to locals, and the walk to Piazza Grande takes only 10 minutes.
For a rural Tuscan escape, the Val di Chiana south of Arezzo is studded with agriturismi, restored farmhouses, and small luxury retreats. The landscape is rolling fields of sunflowers and olive groves, with the white Chianina cattle that give Arezzo its famous bistecca. You will need a car, but the rewards are silence, space, and views.
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Spring (April–June) and early autumn (September–October) offer mild weather, fewer crowds, and the Giostra del Saracino jousting tournaments in June and September. The first-Sunday-of-the-month antique fair runs year-round.
Arezzo is on the main Rome–Florence rail line. Direct trains from Florence Santa Maria Novella take about 1 hour. By car the A1/E35 autostrada covers the 80 km in about 1 hour 15 minutes.
Absolutely. Arezzo is one of Italy's most under-rated cities — Etruscan in origin, home to Piero della Francesca's Legend of the True Cross frescoes, the filming location of Life is Beautiful, and Italy's largest monthly antique market. It offers authentic Tuscany without the crowds of Florence or Siena.
The Fiera Antiquaria di Arezzo is Italy's oldest and largest antique fair, held on the first Sunday of every month (plus the preceding Saturday) in Piazza Grande and surrounding streets. Founded in 1968, it draws over 500 dealers selling furniture, jewellery, ceramics, prints and curiosities.
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