Arezzo, Cortona
and Montalcino
Two nights in a castle hamlet near Arezzo, three below Cortona, two among the vineyards of Montalcino.
Eastern Tuscany, from Piero della Francesca to Brunello
The quieter side of Tuscany: Arezzo and its frescoes, the walled villages of the Valdichiana, Cortona looking down towards Lake Trasimeno, and then west across the clay hills of the Crete Senesi to Montalcino and the Abbey of Sant'Antimo.
- 1Arezzo 2 nights
- 2Cortona 3 nights
- 3Montalcino 2 nights
7 days, 3 homes
For every stop: what to see and where to go, the dishes to try and where to eat them. Below, two or three of our homes in the area, with live rates for your nights.
Arezzo and the Valdichiana
Arezzo is a prosperous, unhurried city of goldsmiths and antique dealers, and home to one of the great fresco cycles of the Renaissance.
What to see & where to go
- Piero della Francesca's Legend of the True Cross in San Francesco
- Piazza Grande, sloping and arcaded
- The Duomo and Piero's Mary Magdalene
- The antiques fair, on the first weekend of every month
- Monte San Savino and Lucignano, walled villages of the Valdichiana
- Anghiari and the Casentino castles
What to eat
- Chianina beef, grilled as bistecca
- Pappardelle with duck ragù, an Arezzo classic
- Grifi all'aretina, slow-cooked veal cheek
- Olive oil from the hills of Arezzo
Where to eat
- Buca di San Francesco, beside the church
- Chianina beef, from the white cattle of the Valdichiana
- Pici with garlic sauce, a local classic
Medieval castle hamlet among woods and olive groves.Why stay hereA whole medieval castle hamlet among the woods, with its own restaurant and a pool in the countryside.See the home
Cortona, above the Valdichiana
Steep, compact and Etruscan in origin, Cortona looks down over the Valdichiana to Lake Trasimeno.
What to see & where to go
- Fra Angelico's Annunciation in the Diocesan Museum
- The MAEC, the museum of the Etruscan city
- Santa Maria del Calcinaio, below the walls
- The Eremo delle Celle, a Franciscan hermitage in the woods
- Montepulciano and a Vino Nobile tasting
- Lake Trasimeno and Castiglione del Lago
What to eat
- Chianina beef from the Valdichiana
- Pici with meat ragù
- Crostini neri, toasted bread with chicken-liver pâté
- Cortona Syrah
Where to eat
- Osteria del Teatro, in the old town
- Dinner among the vines at Il Falconiere
- A bistecca of Chianina beef, cooked rare
17th-century villa among vineyards, with a starred restaurant.Why stay hereA 17th-century villa near Cortona with a Michelin-starred restaurant, spa and pool.See the home
Hotel and spa in a former monastery.Why stay hereA former monastery in Cortona, with a spa: the old town is right outside the door.See the home
Montalcino and the Crete Senesi
West of the Valdichiana, the clay hills of the Crete Senesi lead to Montalcino, the hilltop town of Brunello.
What to see & where to go
- The Abbey of Sant'Antimo, in a valley of olive trees
- The Abbey of Monte Oliveto Maggiore and its frescoes by Signorelli and Sodoma
- Montalcino's fortress
- A Brunello di Montalcino tasting at a historic estate
- The Crete Senesi road from Asciano
- Buonconvento and San Quirico d'Orcia
What to eat
- Brunello and Rosso di Montalcino
- Pici all'aglione, hand-rolled pasta with garlic and tomato
- White truffle from the Crete Senesi, in autumn
- Pecorino di Pienza
Where to eat
- Osticcio in Montalcino, with a view over the Val d'Orcia
- Fiaschetteria Italiana 1888, the historic café on the main square
- Pici and pecorino from nearby Pienza
18th-century villa of the bishops of Montalcino.Why stay hereAn 18th-century bishop's villa on a Brunello estate near Montalcino, with pool, restaurant and tastings on the grounds.See the home
Country relais with a pool, between Siena and Arezzo.Why stay hereA country relais in the Crete Senesi, with pool and solarium, between Montalcino, Siena and Arezzo.See the home
Ask our assistant
This itinerary is a starting point. Tell the assistant your dates and constraints and it re-plans the stops on our homes, then checks the rooms.
- We only have 7 days: which stop do we cut?
- Same route but with two children under 10: which homes work?
- Can you check the three homes for arrival on May 4?
