One week in Tuscany with Cortona as a home base
Experience life in a small historical town and easily move around the region
6 days

Here is a time-based tour for one week in Tuscany with Cortona as home base. This is a great itinerary for all those interested in exploring what Tuscany has to offer. Explore art, the main cities, great food, thermal baths and nature, all while immersed in the remarkable landscape.

Why Cortona? When visiting Tuscany, Cortona makes a great home base as you get to experience life in a small Tuscan town, but in close access to the main roads. Located about 20 km far from Lake Trasimeno, from Cortona you can easily reach the major art cities of Siena and Arezzo (40 minutes), the well known cheese and wine towns Pienza and Montepulciano (even closer), and two different thermal baths at Chianchiano or Rapolano.  

Frances Mayes's Under the Tuscan Sun is set in Cortona and has made the town ever more popular in recent years.

We suggest that you rent a villa outside Cortona or an apartment in town for one week and just slow down, drink up the atmosphere and a good glass of local red wine. Here is a suggested day-by-day itinerary that fits in plenty of the sites, but also makes lots of time to relax.

Day one
Hang out in Cortona
Cortona city centre
Cortona city centre - Credit: John Morton

Take all the time to get to know the town, find its stores and amenities as described here. This itinerary is wonderfully laidback, we don't suggest that you do too much each day, but rather return often to your temporary home in Cortona to simply sit in piazza Garibaldi and take in the view.

The best place to start touring the town is from piazza della Repubblica and piazza Signorelli. Until the 13th century, these two squares were in fact one space and also the site of an ancient Etruscan-Roman forum. Both are framed by medieval buildings and shops.

The Palazzo Comunale (Town Hall)with its impressive stairway and the giant clock tower, sits at the southern part of piazza della Repubblica. Take the opportunity to visit the Museo dell’Accademia Etrusca, Fra Angelico’s panels in the Museo Diocesano, the Medieval Church of San Francesco and the Church of Santa Maria Nuova, built by Giorgio Vasari. Of course, enjoy piazza Garibaldi where you can see Lake Trasimeno in the distance. 

If you're in the mood for a walk, your next stop could be the Girifalco Fortress, also known as the Medici Fortress because it was restored and modified in 1561 by Grand Duke Cosimo I de 'Medici. Located at the highest point of the city (about 1km from piazza della Repubblica) it hosts many events and festivals such as Cortona on the Move: the international exhibition of contemporary photography which is held every year from July to September. From the top of the tower, you can enjoy a breath-taking view of Cortona and the entire Valdichiana. 

Day two
Siena and the Crete Senesi
 - Credit: Mirella Bruni

The road that conects Cortona to Siena crosses the Crete Senesi, or Senese clays, with its famous winding roads lined with cypress trees and wheat fields. Be sure to make a stop near Asciano, along the Strada Provinciale del Pecorile, to snap a photograph of one of the most instagrammed spots of this countryside: the agriturismo Baccoleno.

Once in Siena, you'll be spoilt for choice. The city has plenty to offer for a day's tour. Start in piazza del Duomo with a visit to the Cathedral famous for its intarsiated marble floor and for the Piccolomini Library with renaissance frescoes by Pinturicchio. Across from the Duomo is the large museum complex of Santa Maria della Scala, previously a pilgrims' hospice and now used for special exhibits. 

It's time to visit Piazza del Campo, one of the most beautiful squares in the world and the setting of the famous Palio Horse race. Overlooking the piazza is the city hall, the so called Palazzo Pubblico which is home to the civic museum. The civic tower, or Torre del Mangia, stands tall at 87 metres in height and it's the third tallest historic tower in Italy. You can reach the summit by climbing 300 steps to enjoy a one-of-a-kind view of the entire city.

Day three
Thermal baths and outlet shopping
Rapolano Terme
Rapolano Terme - Credit: mikeccross

Located 23 km from Cortona, the outlet at Valdichiana has a great selection of mens and womens clothing and accessories, as well as store with kitchen supplies. Definitely worth spending a few hours (and euros) here.

As for thermal baths, this area is rich in sulfur waters, so you can choose between Rapolano Terme or Chianciano Terme. In Rapolano Terme, you can choose between two attractive thermal establishments: Antica Querciolaia and San Giovanni Terme Rapolano. In Chianciano Terme, in addition to the thermal pools of Theia, you can find the Sensory Salon with 20 different experiences including aromatherapy, chromotherapy, musical therapy and calidarium. Bring your flip flops, bathing cap, and a robe! 

Day four
Wine & cheese party
Pienza cheese
Pienza cheese - Credit: Josh

Enjoy the best of Tuscany's food with cheese in Pienza, followed by a wine tasting in nearby Montepulciano. Pienza is also historically important; it's layout was entirely constructed in the Renaissance, complete with an interesting church and other public buildings. Together with the whole of the Val d’Orcia, Pienza was recognized as a UNESCO World Heritage Site.

If Pienza is synonymous with cheese, Montepulciano is the capital of Vino Nobile. Walking around the city center, you can visit the centuries-old cellars set in underground tunnels carved into rock. Visit one of them and taste the famous Vino Nobile di Montepulciano, defined by the poet Francesco Redi as the King of all wines.

Day five
Arezzo and Monterchi
Monterchi landscape
Monterchi landscape - Credit: Franco Vannini

Arezzo is the closest large town to Cortona. Get a map and explore this city, starting perhaps with the church of San Francesco and its frescoes of the True Cross by Piero della Francesca. In the Duomo, you'll find Mary Magdalene, made by the same hand. If you're lucky enough to time your visit with the Arezzo Antique Fair that takes place the first sunday of the month, be prepared for crowds but also for the possibility of finding a real treasure to take home!

After leaving Arezzo, you're likely to be keen to seek out more works by Piero della Francesca. You can take a small road to Monterchi to visit the Madonna del Parto, a fresco by Piero that's believed to have magical properties with regards to assisting in pregnancy and birth. Local women still pray to her.

Day six
More small towns or a hike

A long hilly hike followed by a nap is just what you need to complete your trip. Follow the road that goes to the Eremo di Celle, the 13th-century hermitage founded by Saint Francis. This path is only 3 km long. It passes by the Basilica di Santa Margherita at the top of the town of Cortona. If you want to take a longer walk, you can follow the Way of Saint Francis which continues towards Sansepolcro, passing by Castiglion Fiorentino and Arezzo. 

If hiking is not your thing, go check out any of the other small towns in the area, including Castiglion Fiorentino, a city of Etruscan origins and a wealth of museums and artworks or Foiano della Chiana, where the most historic carnival in Italy is held.