Exploring the Val di Chiana: Hidden Tuscany by Train!
- realtravelguides
- Oct 15
- 2 min read
The Val di Chiana, stretching between Arezzo and Siena, is classic Tuscan countryside — cypress-lined hills, vineyards, and medieval villages. Yet it’s less visited than Chianti or Val d’Orcia, making it a peaceful and delicious escape.
Why Go?
This valley combines easy rail access with hilltop towns full of art, slow food, and traditional life. It’s Tuscany without the tourist buses.
A bit of History
Once marshland reclaimed by the Etruscans and Romans, the Val di Chiana became fertile farmland and a key trade route. Home to the medieval attractions of Cortona and Castiglion Fiorentino, its lesser-known towns — Monte San Savino, Lucignano, and Foiano della Chiana— also flourished in the Renaissance.
What to Expect
Warm, small-town hospitality.
Hilltop views and hidden frescoes.
Excellent local cuisine and wines.
Towns to Visit and What to See
Arezzo – Start your journey here, visiting Piero della Francesca’s frescoes in San Francesco.
Cortona – A sun-drenched hilltop town with sweeping views over Lake Trasimeno, known for its Etruscan roots, Renaissance charm, and relaxed café culture.
Castiglion Fiorentino – A medieval gem between Arezzo and Cortona, crowned by its ancient fortress and beloved for local festivals and rustic Tuscan cuisine.
Monte San Savino – A local culinary hotspot, known for its pork dishes and Renaissance Loggia dei Mercanti.
Lucignano – Perfectly circular medieval hill town with the Tree of Life in its museum.
Foiano della Chiana – Famous for its Carnival and Chianina beef.
Civitella in Val di Chiana – A medieval village with panoramic views and WWII history.
Food Culture
This is Chianina beef territory — the original Florentine steak. Expect hearty soups, handmade pici pasta, olive oil, and Montepulciano wines.
Where to Eat
Osteria del Teatro (Cortona) – Renowned for elegant Tuscan classics.
Ristorante Il Goccino (Lucignano) – Seasonal local cuisine, beautiful terrace.
Le Bindi (Monte San Savino) – Fabulous multi-course, no menu Tuscan cuisine extravaganza, where you eat at one shared table - meeting new people and tasting multiple courses in a unique family-style setting. Booking essential!
Agrituristica Poggio San Piero (Foiano della Chiana) - outstanding locally sourced food and great service in a country farm setting just outside Foiano.
Where to Stay
Fattoria Santa Vittoria (Foiano della Chiana) – Panoramic apartments with swimming pool, winery tours, truffle hunting, cooking classes and exquisite wine pairing.
Hotel Villa Marsili (Cortona) – Set within the town walls of medieval Cortona, this impressive 18th-century residence offers you spectacular views of the mountains, hills, and nearby Lake Trasimeno.
Off the Beaten Track
Cycle the Sentiero della Bonifica, a scenic 62 km trail following old canals between Arezzo and Chiusi.
How to Get There by Train
Regional trains from Florence or Rome stop at Arezzo, Monte San Savino, and Castiglion Fiorentino, from where short taxis reach the hill towns.
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