Things to do
We hope you’ll be able to make the most of your time in Italy. Here are some highlights in and around Cortona.
Nearby towns
Montepulciano
Known for its food and wine, this hilltop medieval town is a lovely trip. Have lunch in the garden at La Grotta, at the same time enjoying the Renaissance church of San Biageo nearby. Or visit a cavern winery called Cantina de' Ricci where you can indulge in wine-tasting accompanied by delicious Tuscan antipasti.
30 mins away by car from Cortona
1 hour away by train from Cortona - note there is one change. Train schedule can be viewed here.
Siena
There is a lot to see in Siena, so it’s best done as a day trip. A stunningly beautiful Gothic city, the focus is the Piazza del Campo. (The Palio takes place here twice a year, in July and in August.) The cathedral has to be seen to be believed!
Our favourite restaurants are La Taverna di San Giuseppe and Gallo Nero.
1 hour away by car from Cortona
2 hours away by train from Cortona - note there is one change. Train schedule can be viewed here.
Lake Trasimeno and
Castiglione del Lago
Take the local ferry to reach Isola Maggiore, one of three islands in the centre of the huge lake, where fish restaurants await you in the tiny village. You can catch the ferry from Castiglione del Lago, the largest town on the lake, where the fortress Rocca del Leone is also worth a visit, with a wander along the walls overlooking the lake.
25 mins away by car from Cortona (but Isola Maggiore is a full day’s trip)
10 mins away by train from Cortona. Train schedule can be viewed here.
Montone
A short drive away from Borgo di Bastia Creti is a charming small medieval village, dubbed one of Italy’s 100 Most Beautiful Villages. A view from the top at sunset will remind you of a Renaissance painting!
Hint: Delicious food is to be had at Erba Luna
Val D’Orcia
This beautiful area of south-east Tuscany has been designated a World Heritage site. Vast open hillsides topped by farmhouses, tall cypresses, and vineyards form the quintessential Tuscan landscape. Pienza is a Reanissance town worth visiting, and La Foce is the beautiful house & garden developed by Iris Origo, author of War in Val d’Orcia.
1 hour away by car from Cortona
Bagno Vignoni
The ancient village of Bagno Vignoni dates back to Roman times where its thermal waters were discovered and used as baths. The town square is an ancient pool filled with the hot springs water, although you’re not allowed to use them these days... We’d recommend the spa hotel Albergo Le Terme, which sits in the town square too and has its own baths.
1 hour 15 mins away by car from Cortona
Activities in & around Cortona
Convent de Le Celle
This 13th-century Franciscan convent is located in Le Celle, just outside Cortona. The rustic stone buildings are beautifully cut into the mountainside, sitting atop a stream and surrounded by woods. St Francis (the patron saint of Central Italy) lived as a hermit for six months in a cave here, and monks from the Capuchin order still inhabit the convent.
10 mins away by car from Cortona
Fine dining
You generally can’t go wrong wherever you go, but if you want a special meal around Cortona, here are a few of our favourites: Osteria del Teatro, Caffè del Teatro, La Bucaccia, Villa Di Piazzano and to splash out, Il Falconiere Restaurant is a Michelin star worth visiting.
Villa Di Piazzano & Il Falconiere are a 10 min taxi outside Cortona
Walks
September is usually a gorgeous month for walking and trekking (clear, blue skies, warm temperatures during the day but usually not too hot!) Ideas for walks nearby can be viewed here.
There are many ancient Etruscan routes in and around Cortona, such as a walk up to Cortona from the church in Sant’Angelo.
Art
If you’re interested in art and Piero della Francesca, here’s an itinerary from Normi & Alastair to follow the famous Renaissance artist’s masterpieces.
Sansepolcro
Piero della Francesca was born in Sansepolcro, where some of his paintings can be viewed at the Museo Civico, including Virgin Mary of Mercy, and The Resurrection.
Monterchi
The moving portrait of Virgin Mary Giving Birth (Madonna del Parto) has been relocated from its original chapel to this small exhibition centre in the village of Monterchi.
Hint: A nice meal can be had at Ristorante La Pieve Vecchia just outside Monterchi.
Arezzo
One of our favourite towns. It’s best to park in one of the carparks just outside the city wall. It has a stunning square, one end of which is the 10C cathedral Santa Maria della Pieve with an original 14C altarpiece by the Sienese artist, Pietro Lorenzetti.
Piero della Francesca’s stunning fresco of The Legend of the True Cross can be viewed at the nearby Basilica of San Francesco.
Hint (more delicious food!): Near the Basilica di San Francesco is our favourite restaurant in Arezzo, Antica Fonte.
Shopping
The Via Nazionale is a little high street that runs through the centre of Cortona with lots of shops, small galleries, bars and of course gelaterias. Laura’s favourite is Marri if you want to spend a small fortune!
For those who want to venture further afield, the Valdichiana Outlet store is 25 mins away by car and features some good Italian brands.
Wine tasting
Tuscany is filled with superb vineyards. Nearby you could try Avignonesi or Montepulciano’s Cantina de'Ricci. Alternatively, a bit further, on your way over or back from Florence, stop at Antinori’s winery which has spectacular modern architecture.