The province of Arezzo is in Eastern Tuscany, Italy. It includes the renowned Medieval hilltop town of Cortona, the Natural Park of the Casentino Forests and plenty of small towns with an enchanting out-of-the-way atmosphere.

There’re monasteries here too, legacies of Saint Francis of Assisi who lived in this area for part of his life. This area also gave birth to some artistic talents, including Michelangelo Buonarroti whose home town has adopted his name, Caprese Michelangelo.

To make things easy, we’ve arranged the attractions into the three geographical areas of the Arezzo province in Tuscany, and listed the main sights by area.

things to do in tuscany in autumn

Discovering Eastern Tuscany – the Val di Chiana

Stretching from Arezzo to Siena, this was Etruscan territory and the home of the famous “Chianina breed of cattle. The most succulent of the famous steak bistecca alla fiorentina comes from here.

Highlights of the Val di Chiana:

Cortona – is the most famous town in Eastern Tuscany, scenic and quite touristy. A lot of its publicity came from the novel “Under the Tuscan sun”, written by Frances Mayers , an American writer-turned local. Cortona boasts Etruscan remain, picturesque Medieval streets and breathtaking views.

Le Celle Hermitage – lies a few kilometres from Cortona, a monastery in a peaceful natural setting, infused with the spirit of San Francesco.

Lucignano – romance is always just around the corner in this small Medieval town. It has one particularly unique sight that everyone falls for: the Tree of Love.

small towns in tuscany
Cortona – photo @vidalouca1970 pixabay

What to see in the Casentino area

Easily reached from Florence on the scenic SR70, the Casentino is north of Arezzo. It is a prosperous part of Eastern Tuscany, famous for its goldsmiths and wool products. Among its guests it counted Saint Francis and the father of the Italian language, Dante Alighieri.

In this area you’ll see some of the most atmospheric Medieval country churches and monasteries in Tuscany. Spirituality and nature, forests and sacred mountains, small hamlets nested in the woods. The hills are covered by ancient woodland (Natural Park of the Casentinesi Forests), and the river Arno has its source here on the slopes of Mount Falterona. A great destination for walkers and peace seekers.

⇒ Discover the Best of Casentino with our 2 Day Road Trip.

Highlights of Casentino:

Poppi– an attractive small town and the site of the spectacular Conti Guidi castle, that dominates the valley.

Pieve di San Pietro a Romena (Pratovecchio) – the best example of Romanesque pieve (country churches) in Casentino.

La Verna Franciscan Sanctuary an atmospheric place situated on the mountain where Saint Francis received his stigmata. This is where he founded his religious community that is still alive today.

National Park of the Foreste Casentinesi (15 km. north of Poppi) – this is a walkers paradise. It’s one of the oldest forests in Europe with plenty of trails catering for walkers of all levels.

eastern tuscany

Valtiberina in Eastern Tuscany

Renaissance masters Piero della Francesca and Michelangelo Buonarroti both come from Val Tiberina. Art fanatics often make pilgrimages here to visit Caprese Michelangelo, home town of Michelangelo, genius of the Renaissance and creator of the statue of David. Don’t miss the small museums dedicated to the mesmerising works of Piero della Francesca, born in San Sepolcro.

Highlights of the Valtiberina:

Anghiari – a quaint town with a Medieval feel and a creative atmosphere. You’ll find plenty of antique dealers and it’s home to a thriving artisan community.

Caprese Michelangelo – Home town of Michelangelo Buonarroti. You can still see the church where he was baptised and the house were he was born, now a museum.

San Sepolcro and Monterchi Museum – See the masterpieces by Piero della Francesca in the Madonna del Parto Museum in Monterchi and in the Museo Civico in San Sepolcro. => Check out our Piero della Francesca artworks itinerary.

=> 10 Beautiful small Towns to visit near Arezzo

Anghiari – photo luis-garden

Shopping in Eastern Tuscany

There are two worthwhile shopping outlets in the area. The Space Outlet in Montevarchi is a pleasant place to shop and has plenty of cafes and restaurants too. The Outlet Valdichiana is in Foiano della Chiana. It’s a nice setting and has a relaxing atmosphere, with plenty of shops selling famous brands.