Cortona Italy is a beautiful town set in the hills of Tuscany. It’s made up of countless winding streets and colorful architecture, all of which overlook the legendary Lake Trasimeno and Val di Chiana below. The historic sites and delicious restaurants make it the perfect place to visit on a day trip from the nearby towns of Tuscany, or even cities like Florence! Here are the best things to do in Cortona and why it’s such a must-visit destination in Italy.
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How to Get to Cortona Italy
Cortona Italy is an hour and a half from Florence and less than one hour from the popular city of Siena. On our visit, we came from the medieval village of Montepulciano, which is one of the most famous towns nearby.
One thing to know about Cortona is that it is actually VERY large compared to the other “villages” in the area. Make sure to give yourself at least a few hours to explore all the backstreets, castles, and local shops.
There is a main parking area just outside the city walls with very few places to do so within Cortona. Keep in mind that the historic center is limited to cars and only allowed during certain hours or days. It’s honestly better to just avoid driving through Old Town in general.
If you aren’t planning on renting a vehicle, you can take public buses, the Tuscany hop on hop off tourist bus, or jump on a group day trip from Florence!
Where to Stay in Cortona Italy
Although many travelers visit Cortona in Italy on a day trip, if you have the time it is a great place to stay! Options range from historic hotels to traditional bed and breakfasts. They have a homey feel and give off welcoming Italian vibes that every traveler will love. Many even have epic views of Cortona and its natural surroundings in the green heart of Italy.
Ultra Luxury – Monastero Di Cortona Hotel & Spa – This gorgeous hotel and spa is situated inside an ancient monastery! Enjoy all the luxury amenities you love inside this historic building near town.
Fun Vacation – Hotel San Luca – Beautiful hotel with views over Cortona from the terrace. You’ll also be just a quick drive to Lake Trasimeno.
Historic Hotel – Hotel San Michele – Located inside the Baldelli Palace which is one of the oldest buildings in Cortona Italy. Live like kings and queens inside this 15th century mansion!
Apartments – Le Residenze Ristori – Apartment-style rooms with wifi, TV’s, and a kitchenette. Great place to stay near everything inside the city walls.
Quick History of Cortona
It is impossible to explain the history of Cortona Italy in just a couple of paragraphs. However, it’s important that you get the gist of it before your visit! Cortona is known as the “mother of Troy and grandmother of Rome.” Legend has it, that the ancient hero Dardanus left Cortona to found Troy, while Aeneas founded Rome hundreds of years later.
It is believed that around 5th century BC Cortona was one of a dozen Etruscan cities in the area around Lake Trasimeno. Soon after, the Romans would come through to conquer and change this entire region. Evidence of both time periods from over 2,000 years ago can be seen in the very walls and tombs of the ancient city.
The more modern history (still very old!) is just as interesting as the Roman and Truscan periods. Many buildings and churches still standing date back hundreds of years within the historical center of Cortona.
The crown jewel is the fortress that sits high above the city and dates back to the 13th century. One of the best things to do in Cortona Italy is to visit the many museums in town. Don’t miss out on the Diocesan and MAEC museums after exploring the historical center!
Best Things to do in Cortona Italy
Explore the Historic Town Center
When visiting the town of Cortona Italy make sure to wear some extremely comfortable walking shoes! The town is built into the mountainside making it very steep. There are plenty of small side streets to explore, but when you first arrive in town head toward Piazza della Repubblica.
This is the heart of Cortona, with many of the best bars, cafes, and restaurants located nearby. A large staircase heads up to the 13th century Palazzo Comunale, which is a nice place to sit and take in the view. From the main square stretching all the way down via Nazionale, is filled with restaurant tables that spill into the city streets.
You can find everything from small cafes and bars for drinks to fine dining restaurants, gelato shops, and pizza by the slice. In the summer months, this sleepy mountain village comes alive with both tourists and locals out enjoying life.
Hike to the Castle of Cortona in Italy
If you’re up for a steep climb then a trip to the Cortona Castle is a must! Also known as the Fortress of Girifalco, this historic site has been key to the city’s defense for hundreds of years. Even though the current castle dates to 1258, experts agree there was likely a fortress here all the way back in 6th century BC during the Etruscan period.
Although it has such a strong look to it, the castle couldn’t withstand the constant attacks during the wars with Arezzo. Eventually, it was sold along with the city of Cortona to the Florentines in 1411. Over the next few centuries, it would undergo much construction. Ironically, it would never be used in battle again.
Epic Views of Val di Chiana
One of the best things to do in Cortona is to simply admire the beautiful views of Val di Chiana! The highest point is from the castle described above. Yet, you’ll be happy to know that there are amazing viewpoints all around Cortona in Italy.
Even if you just want to hike a little ways up the hill, you can get to different views and vantage points of the city and Chiana Valley. Val di Chiana is one of the most beautiful in Central Italy and lies across both the Tuscany and Umbria regions. If you’re limited on time, one of our favorite views is by the Garibaldi & Republic Memorial & Monument.
See the Cortona Churches & Tombs
Another thing to see both up close and from afar is the many churches of Cortona Italy. Religion is as much a part of Tuscany’s history as anything, and this is a common theme around the country. Below are some of the must-see religious sites in and around Cortona.
Monastery of Celle: First monastery built by St. Francesco of Assisi in the early 13th century. Located about 10 minutes from Cortona and is inhabited by Friars to this day.
Church of Santa Margherita: Named after the patron saint of Cortona and constructed next to the Fortress of Girifalco around the same time period.
Church of Santa Maria delle Grazie: 15th-century church and some of the most recognizable Renessaince architecture from the hills of Cortona.
Etruscan Tombs: Incredible ancient tombs that were uncovered in the early 1900’s. They are in the Archaeological Park of Sodo about 2.5 miles from Cortona.
Santa Maria Nuova Church: Another remarkable church just outside of the walls of Cortona Italy. It was designed by famous architect Giorgio Vasari, and its dome-shaped top can be seen from long distances.
Enjoy the Delicious Food of Cortona Italy
Along with its great history and architecture, you can find all your favorite Tuscan dishes and drinks in Cortona Italy! From Chianina beef and local pasta to truffles and pecorino cheese, there are endless delicious meals to try here!
If you’re not starving or want to keep it cheap, you can stop in at one of the many pizza shops for a quick bite. In the summer it’s common to see everyone outside enjoying an Aperol Spritz or glass of wine.
Below are some of the best restaurants to check out on your trip to Cortona in Italy! For dinner, we highly recommend making a reservation in advance.
- Relais La Corte dei Papi
- Trattoria Toscana
- Pizza place we went to
- Osteria del Teatro
- La Bucaccia da Romano
- Bar 500
Relive the Movie Under the Tuscan Sun
An American writer moves to Tuscany and rebuilds an old villa into her new home… Stop us if you’ve heard this one before! One of the most famous movies about Italy was actually filmed right here in Tuscany.
Under the Tuscan Sun was first a best-selling book, and now tourists from all around the world come here to see the house. Today you are free to visit “Villa Bramasole” as many do just outside of Cortona. It’s about 30 minutes walking from the city center and you can even buy olive oil from the house!
Have any questions on this article, Val di Chiana, or want to share your own favorite things to do in Cortona Italy? Leave us a comment below!
Brigitte & Jake
Where in the world are we? Follow our daily adventures on Instagram @nothingfamiliar!
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Italy Travel Planning
Flights: We always check Skyscanner and Kayak to search for cheap flights. That’s how we got from Rome to Venice for under $30 USD!
Accommodation: Compare multiple sites to get the best deal such as Booking.com and Agoda! Also, Hostelworld should be your go-to source if you’re traveling on a budget.
Rental Car: We use Discover Cars to explore when traveling. Consider renting a car in one city and dropping it off in another for an epic Italian road trip!
Tours: Check out Get Your Guide for thousands of activities around the world. Book a Florence winery tour, Capri Boat trip, or street food tour with a local guide in Rome!
Travel Insurance: Never travel abroad without protection! We’ve been using SafetyWing for the last few years on the road and they are there when we need them.
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Can you drive to Cortona from Rome?
Or would it be better to train to Sienna then rent a car?
Hi Judi! You can easily make the drive from Rome to Cortona in about 2.5 hours. If you have a little extra time you could even take the backroads instead of the highway to explore more of the Tuscan Countryside! Have fun!