Under the Tuscan Sun: Cortona as a base to explore Tuscany and Umbria

Cortona holiday Guide Tuscany

Why Cortona as a base to explore Tuscany and Umbria in Italy? Cortona is one of the most beautiful and fascinating hill towns of Tuscany and Italy. The origins of this small and suggestive village go very far back in time, and you can still admire part of its imposing Etruscan walls.

High, on top of a steep hill, Cortona offers one of the most breathtaking and vastest panorama of all Tuscany. Its location near Arezzo southeast of Tuscany, on the border with the Umbria region, makes it a great home base to explore some of the most impressive sights and attractions of both regions.

Cortona is a great town in itself, with an enchanting countryside and a fabulous landscape, offering a lot to any tourist: great art and culture at the notable Etruscan Museum, great events like the Tuscan Sun Festival, beautiful monuments like the fortress of Girifalco and the peculiar Town Hall, not to mention the possibility to enjoy a lot of outdoor activities, like cycling or trekking. Read our mini-guide to visit Cortona for more information.

Cortona has everything to make your holiday in Tuscany absolutely fantastic! A great base to visit Tuscany and Umbria.

If you choose Cortona as your home base, a car is recommended, though the train station of Cortona Terontola can be very convenient to reach major art towns like Florence and other destinations in Tuscany.

The Best Day Trips from Cortona


Here is an interesting itinerary that covers most of the must see visits and most popular destinations in Tuscany, using Cortona as your starting point:

  • Florence, the art town par excellence, the first on your list of the things to see in Tuscany! I suggest you reach Florence by train, as driving in Florence can be quite stressing and there is few parking. Just at the feet of Cortona, you find the train station Cortona-Terontola, from where you can take a train arriving directly in Florence town’s center in about 1 hour and half. Train timetables on Trenitalia.com.
  • Arezzo, located north of Cortona, can be reached in about 40 minutes driving. Arezzo is a very charming and quiet art town, with a beautiful main piazza with loggias. Roberto Benigni chose Arezzo as a location for his Oscar winning movie “La Vita è Bella”.
  • Siena, so famous for its Palio horse race, is a must visit for anyone visiting Italy! Its beauty is incomparable, a lot to visit any part you turn. Just walk its alleys and medieval streets to fall in love with it forever.
  • Monteriggioni is a tiny hamlet near Siena that is unique in itself. Still perfectly enclosed by thick medieval walls and bastions, it retains the unique charm of a village suspended in time.
  • San Gimignano, so famous and well known for its many medieval towers, is one of the most beautiful and peculiar hill towns of Italy! Here there’s a lot to discover and visit beyond the towers.
  • Montepulciano is the perfect medieval Tuscan town to fall in love with! Home to the prestigious Nobile di Montepulciano red wine, this village has a unique atmosphere and wonderful palaces. Its smaller alleys are enchanting and offer lovely views over the valley.
  • The Val d’Orcia is the most spectacular countryside you may admire in Tuscany! Visit it and its fabulous hill towns and top sights, including Montalcino, Pienza, Bagno Vignoni, San Quirico d’Orcia, and the beautiful monastery of Sant’Anna in Camprena, special location for “The English Patient”.
  • The Crete Senesi: West Cortona you are in the land known with the name of Crete Senesi for their characteristic and suggestive lunar landscape. Here rise many nice hill villages, while I also suggest you visit the majestic and Abbazia di Monte Oliveto Maggiore, full of surprises. Monte Oliveto is one the most impressive and beautiful abbeys of Tuscany.

If you are interested in visiting also special and lesser known towns and attractions, you may well consider visiting the following:

  • Anghiari, beautiful scenic hill town northeast of Arezzo, is a lesser known place but extremely worth the visit. I speak about it in this list of Tuscany off the beaten path villages.

Great Day Trips to Umbria

Assisi in Umbria

And here follows an interesting itinerary for fantastic day trips to Umbria and its main sights, using Cortona as a base:

  • Lake Trasimeno, few kilometers south Cortona, this large lake with picturesque islands and imposing castles, is simply beautiful! Its characteristic villages facing the lake, like Passignano sul Trasimeno and Castiglione del Lago are lovely and very characteristic. Spending a day on the shores of the lake would be a great idea, especially during spring and summer. The lake is a great place for watersports, fishing, and cycling. Food here is delicious!
  • Perugia, the capital of Umbria, is a superb art town with a great historical heritage. Its medieval streets are beautiful as are its squares and palaces. The famous Umbria Jazz Festival is held here. The wonderful 15th century frescoes by Perugino within Palazzo dei Priori are a spectacle not to be missed.
  • Orvieto, built high on the remains of an ancient volcano, is a spectacular hill town with one of the most beautiful cathedrals of Italy.
  • Deruta is a wonderful hill town, known for the production of beautiful hand made artistic ceramics. Highly recommended.
  • Assisi, just an hour’s drive from Cortona and visible for miles, Assisi is a medieval jewel, and a Unesco World Heritage Site. Here are the beautiful Basilica of San Francesco, and other interesting Franciscan sites.
  • Gubbio, Spello, Todi, and Spoleto are other suggestive and intriguing Umbrian towns that may be worth a visit.

Where to Stay in Cortona

Lying on a fabulous valley surrounded by verdant hills, is the exclusive Relais la Corte dei Papi, luxury hotel with spa, that is ideal to have a superb holiday. Find other accommodations de charme we recommend in Cortona at this link.


  • Enza Lafratta ha detto:

    Could one use Cortona as a base for day trips in Umbria using public transit?

    • elena nacci ha detto:

      Hi Enza,
      thanks for your message,
      You might actually use bus and train to reach some of the best destinations in Umbria, but, as for Tuscany, the best way to move around is by having a car.
      Have a nice day,

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