Cortona and Arezzo — east Tuscany in three days

Why east Tuscany is underrated

The Arezzo–Cortona axis sits in the eastern third of Tuscany, in the Valdichiana valley running up from the Umbrian border. Most tour itineraries don't reach this far east — the Florence-Chianti-Siena loop dominates marketing, and the rest of Tuscany suffers (or benefits) from the lack of attention.

What you get by going east: arguably the greatest single fresco cycle in Italy (Piero della Francesca's True Cross), a perfectly preserved hilltop city (Cortona), Tuscany's biggest antiques fair (Arezzo, first Sunday of the month), the Casentino forests for hiking, and food and wine that's neither Chianti nor Brunello but distinctive in its own right (the cinta senese pig, Vin Santo, the chestnut polenta of the high valleys).

What you give up: the sheer concentration of A-list sights you find in Florence or the Chianti hills. East Tuscany rewards depth over breadth.

Day 1 — Arezzo

Start in Arezzo. The city is bigger and more workaday than Cortona — 100,000 people, working medieval centre, train station with direct Frecciarossa from Florence (35 minutes).

Morning — San Francesco and the Piero frescoes. The headline. Piero della Francesca's Legend of the True Cross fresco cycle in the apse of San Francesco church is the single most important art destination east of Florence. Painted 1452–1466; restored 1985–2000. Booking is mandatory — only 25 people at a time, 30-minute slots, capped at 60 visitors per hour. Book online at pierodellafrancesca-ticketoffice.it 2–3 weeks ahead. €8 entry, allow 60 minutes.

Late morning — the Duomo and Piazza Grande. Walk up Corso Italia from San Francesco. The Cathedral of Saints Peter and Donatus has a Piero fresco of its own (Mary Magdalene) plus the tomb of the bishop-poet Guido Tarlati. Then Piazza Grande — the sloping medieval piazza used as the location for Roberto Benigni's Life is Beautiful (1997) and home of the antiques fair.

Lunch — Antica Osteria L'Agania (Via Mazzini). Honest Tuscan trattoria, 60 years in business. Pappardelle alle lepre. €25–€35 per person.

Afternoon — Casa Vasari and the Basilica of San Domenico. Giorgio Vasari (the painter and art-historian, author of the Lives of the Artists) was born in Arezzo. His house — preserved as he designed it, walls covered with his own frescoes — is open as a museum. Then 10 minutes' walk to San Domenico, which holds Cimabue's painted crucifix (c. 1265–1268), one of the most important paintings in Italian art history.

Late afternoon — the Fortezza Medicea. The hilltop fortress at the top of town has open gardens and the city's best sunset view. Free.

Dinner — La Lancia d'Oro (Piazza Grande). A Michelin-recommended spot directly on the medieval piazza. Modern Tuscan. €55–€75 per person.

Day 2 — Cortona

Drive 30 minutes south to Cortona. Park at Parcheggio Mercato (P2) just below the walls; €1.50 per hour. 5-minute walk up to the centre.

Morning — Piazza della Repubblica + the MAEC. Cortona's central piazza has the 13th-century Palazzo Comunale with its broad open stairway. Off the piazza, the MAEC (Museum of the Etruscan Academy and the City of Cortona) holds important Etruscan bronzes and a small but excellent painting collection (Pinturicchio, Signorelli). €13 entry, allow 90 minutes.

Late morning — Diocesan Museum. Just behind the Duomo. Beato Angelico's Annunciation (1430s), one of the early Renaissance's most reproduced paintings. €5 entry, allow 30 minutes.

Lunch — Trattoria Dardano (Via Dardano). Family-run, traditional, 6 tables, walk-in. Pici al ragù and bistecca. €30–€45 per person.

Afternoon — walk up to the Fortezza del Girifalco. The Medici-built fortress at the top of Cortona's hill, 30 minutes uphill from the centre on cobbled lanes. The view from the ramparts covers Lake Trasimeno and into Umbria. The walk is steep but rewarding; the alternative is the small tourist train (€5 return).

Late afternoon — gelato + slow walk down Via Nazionale. Cortona's main shopping street. Gelateria Snoopy is the standby (despite the name).

Dinner — Osteria del Teatro (Via Maffei). Game-focused menu, intimate, the cinghiale ravioli is the order. €45–€60 per person.

Stay overnight in Cortona — the town transforms after the day-trippers leave. Suggested: Villa Marsili (just outside the walls, 27 rooms, €170–€280) or Relais Villa Petrischio (15 minutes outside town in the countryside, pool, €200–€320).

Day 3 — Casentino and Anghiari

The third day for those staying longer than two nights. Pick one of two directions:

Option A — The Casentino forests. Drive an hour north to Camaldoli, the 11th-century monastery in the heart of the Casentino National Park. Walk in the beech forests; lunch at the monastic refectory (€18 set menu, simple, excellent); visit Eremo (the hermitage 1,000m above the monastery, accessible by car or 90-minute walk). The Casentino was Saint Francis's chosen wilderness; the forests are protected as a national park since 1993.

Option B — Anghiari and Sansepolcro. Drive 45 minutes north-east. Anghiari is a small medieval town famous for the Battle of Anghiari (1440), the subject of Leonardo da Vinci's lost mural commission for the Palazzo Vecchio in Florence. Tiny museum dedicated to the battle. Then drive 10 minutes to Sansepolcro — Piero della Francesca's birthplace, with his Resurrection in the Museo Civico (the painting Aldous Huxley called 'the greatest picture in the world').

The Arezzo antiques fair

The first Sunday of every month, plus the preceding Saturday. Around 500 stalls in Piazza Grande and the surrounding streets; the biggest antiques fair in central Italy. Active since 1968. The mix is genuinely good: 18th-century Tuscan furniture, religious sculpture, ceramics, prints, the occasional astonishing find.

Plan around it if you're collecting or like browsing. Get to Piazza Grande by 9:00 to walk the stalls before they fill. Bring cash; many dealers don't take cards. Bargaining is expected (knock 15–25% off the asking price). Don't try to ship furniture home from a stall purchase — too complicated; smaller items (prints, jewellery, ceramics) travel fine in checked luggage.

Where to eat in the region

Arezzo: Antica Osteria L'Agania (traditional, family-run), La Lancia d'Oro (on Piazza Grande, Michelin-recommended), Le Chiavi d'Oro (modern Tuscan, smart).

Cortona: Trattoria Dardano (walk-in classic), Osteria del Teatro (game-focused), Locanda del Molino (a few km outside town, romantic).

Castiglion Fiorentino: Da Muzzicone — bistecca specialist 20 minutes south of Arezzo, fireplace grilling visible from the table. €35–€55.

For wine: Cortona produces Syrah-based reds under the Cortona DOC — distinct from the Sangiovese-dominated wines elsewhere in Tuscany. The Tenimenti d'Alessandro cellar in Camucia is the best-known producer; €25 tasting with one-week-ahead phone booking.

Practicalities — getting around

From Florence: Arezzo is 35 minutes by direct Frecciarossa (€15–€19) or 1h10 by regional (€9.30). Cortona is best reached by car (1h30) or by train to Camucia-Cortona station (90 minutes from Florence, then a 5-minute bus or 20-minute walk up the hill).

From Siena: Arezzo is 1h30 by car via the SR73. No direct train (you'd have to change at Chiusi).

From Rome: Arezzo is 1h30 by Frecciarossa (€20–€35). Easier than from Florence in some cases.

Hiring a car. Useful for the Casentino + Anghiari day-trip and for getting between Arezzo and Cortona. Pick up at Arezzo station; return there or at Florence's Santa Maria Novella.

Read on

Our Arezzo region pillar covers the wider province. For other east-Tuscany itineraries: day trips from Florence by train includes Arezzo as a 35-minute Frecciarossa stop. The Pienza guide covers south Tuscany; these two pieces together — east and south — give you the half of Tuscany most visitors miss.