Cortona, Italy | A 2-day itinerary

Cortona. This lovely little hill-top town is located in southeastern Tuscany (Italy), roughly 2,000 feet above the sea level, overlooking the Valdichiana (Chiana Valley). Cortona is filled with beautiful views, stony side streets, and little Italian restaurants. Dating back to the Etruscan era and Roman times, the town is surrounded by stone walls (built around 400 B.C.) that run along the outer edge of the city.

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

Cortona in Italy
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Why visit Cortona?


Cortona is a great home base to see many parts of Tuscany including Florence, Siena, Arezzo, and, of course, lots of vineyards. Pienza and Montepulciano, both are well-known wine towns within 30-40 km of Cortona. The city itself has a rich history, museums, churches, tons of shopping, great little restaurants and gives visitors that quintessential small-town Tuscan experience.

How to Get to Cortona


Florence, Rome, and Pisa are the closest major airports to Cortona. From there, you have several options: train, taxi/private driver, or rent a car. I would highly suggest renting a car because then you can enjoy the beautiful scenery on the drive and even stop by a vineyard or two. Plus, it gives you options to visit other areas near Cortona.

By Taxi or Private Driver


A taxi or private driver will cost you anywhere from 150-250 Euros. Probably not the best option for most people. But if you don't want to think, and have others do the driving,

By Train


Visitors can also get to Cortona via train, which takes you right to the base of the city. There are two train stations, Terontola-Cortona or Camucia-Cortona.  It's super easy to use too! But, you will still need to take a taxi or bus to get up to the city centre.

Pro Tip - If you do take the train, and want a taxi, make sure to arrange this ahead of time – they don't just hang out at the station.

Getting to the city centre and parking


Once you get near the city, make sure to give yourself plenty of time to get to the top. It will take you about 10 minutes by car/taxi from the main road to the city proper because the road is very, very curvy.

All of the parking for the city is outside the walls, so you will need to wear your walking shoes! Plus, visitor cars are not allowed inside the city walls anyway.  When you get to the top of the hill via the main road (Casa Sparse Cortona), there will be easily accessible parking right there.

Where to Stay in Cortona


Cortona is divided into two different main areas to stay - within the city walls or outside the city walls. Both are great options; it just depends on what you are looking for.

Inside the city walls, you will find cute little apartments or Airbnb's to rent. Most are on little side streets and offer balconies so that you can take in the vibe of the city.  Upgrade and find one with a view of the valley, you won't be sorry!

If you are looking for a bit more space, stay outside the city walls.  I would highly suggest renting a beautiful Tuscan villa through Hill Town Tours. Each villa is unique and luxurious! They also offer full tour services, including daily breakfast, private drivers, wine tasting, truffle hunting, horseback riding and so much more. If you don't want an entire Villa to yourself, I would suggest La Corte Dei Papi! They have a lovely restaurant and an amazing spa right on-site.

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Day 1 in Cortona


On your first day in Cortona, I recommend the first thing you do is simply wander. The city is lovely, full of little side streets and stony roadways. The vibe is friendly and traditional. There are tons of restaurants, little shops, local bars, and gelato places to check out.

Cortona Town Square

Once you have gotten in a good walk around town, spend some time people-watching or shop at Piazza Della Repubblica. This is the city centre of Cortona, so there are tons of people to see and places to sit. The Piazza has many shops and restaurants to explore and enjoy! Make sure to grab some Gelato and sit on the steps of the Palazzo Comunale - the city's 13th- century town hall and clock tower. Also, take a wander over to Piazza Signorelli located right next to the city centre.

The shopping in Cortona is really nice. They have everything from wine shops to pottery stores, leather shops, and jewellery places - all of which are locally hand-made. The best place to check out is a pottery shop called Casantonio.

Located right on the Piazza, this little gem carries every variety imaginable of hand-painted Tuscan pottery. The owner is very friendly and welcoming! They even ship to the U.S. if you wanted to purchase one of their larger items.

Up next Lunch. There are many restaurants to choose from in Cortona that I would suggest trying a few of them for lunch. Wherever your wander lands you, pick the next place you see. Grab some pizza here, a pastry there. It is a great way to get a feel for the city.

If you feel like giving your feet a rest, sit down and try a meal at Caffe del Teatro. Located in Piazza Signorelli, their dinning terrace sits above the street level giving dinners a great view of the Piazza.

Pro Tip - Make sure to get your shopping and eating done before around 2 p.m. because most of Cortona shuts down in the middle of the day so the locals can take a break. Most places reopen later in the early evening.

Now time for some sightseeing. There are many churches and museums to visit in Cortona. However, the best experience can be found exploring the Santa Margherita Sanctuary. Located at the highest point (1 KM from the city centre) in the city, along with the Girifalco Fortress, this amazing church represents the patron saint of the city. The fortress, also called the Medici Fortress, was restored in 1561 and just can't be missed. Follow the path along the city's Etruscan walls on your climb up so that you can enjoy breathtaking views of the valley and surrounding countryside. You can even see Lake Trasimeno in the distance.



And now time for dinner. You can't go wrong with Italian food and almost every place will serve you something amazing. However, the best place to eat in Cortona is La Logetta. This lovely place has a nice inside area, but the best seat in the house is on their terrace, which overlooks the main Piazza. Sitting here on a warm evening with a nice glass of red wine and a big bowl of pasta - it can't be beaten! Everything they make is homemade with locally sourced ingredients and the place is family-owned. You will find truffles in many of the dishes they offer but you really can't go wrong with any item on their menu.

After dinner, take your time getting back to your car or walking to your hotel/apartment. The streets at night are magical! And many of the little wine bars stay open late.

Day 2 in Cortona


On your second day in Cortona, swing by Pasticceria Banchelli for a coffee and pastry. Relax and watch the city wake up, it's a great way to start the day.

Next, book yourself a Tuscan Experience! There are so many activities that will help you immerse yourself in the local culture. Most of these tours can be booked through local tour companies. Please note - all of these must be booked in advance. Here are a few good options:

Tuscan Cooking Class (5 hours) - You will be able to find classes all over the Cortona area both in town and in the country-side. Participants learn how to make traditional Tuscan dishes!

Truffle Hunting (6 hours) – You get to follow around the adorable truffle-hunting dog and dig up these delicious treats! Then, you are treated to a truffle themed lunch after the hunt.

Wine Tasting Tour (Full or half-day tours) - Cortona is located in Tuscany after all, and has many vineyards within a short driving distance from the city. Having a driver allows you to fully enjoy yourself without worrying.

Vineyard tour

Other unique experiences include, a falconry experience, drive a Ferrari, bike tour, horseback riding, art tour, olive oil tasting, off-roading tour, and many more. There is something fun for everyone to do!

On your way back to Cortona, pay a visit to the very famous Under the Tuscan Sun House, Villa Laura.  Located just 3 km from the city centre of Cortona, this amazing villa is available to rent. The public is not allowed to tour at this time, but you can still drive by and catch a glimpse.

Get yourself back into the city proper for dinner. I suggest dining at La Bucaccia - they have amazing steak (prepared rare as is the Tuscan tradition) and chestnut ravioli. Another good option is Osteria del Teatro – try the truffle fondue!

At the end of your two days in Cortona, you will find that it just wasn't enough! Cortona is such a charming city located in an amazing area of Italy, you will want to come back again and again.

Submitted by Sara Moore from WanderMoore

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