Cortona (Tuscany), Italy

Cortona, Italy epitomizes the image of a Tuscan hillside town. While tourists keep the town abuzz, locals also fill the winding hillside streets and town park. Fortification walls encircle Cortona’s medieval stone-clad buildings to further the town’s history. As such, cars very rarely drive through the center of town. The main street, Via Nazionale is full of small shops and restaurants, and ends in two grand piazzas. One of these piazzas is the home of Cortona’s main bell tower, and the other is the home of weekly markets.

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Cortona is especially famous because of the book and movie Under the Tuscan Sun. This movie is both based in and filmed in Cortona. In fact, the author, Frances Mayes still lives just up the hill from the city walls! Make sure to watch the movie before visiting Cortona, as it was filmed here, so you will recognize many of the landmarks seen in the movie.

Cortona is easily accessible by train from larger Italian cities such as Rome or Florence. (A bus picks tourists up from the train station and drives them up to Cortona.) Alternatively, you can rent a car to travel from one place to the next. Cortona is also a great jumping off point for day trips to other Tuscan towns for those interested in exploring Tuscany.

Where to Stay in Cortona, Italy

View from Hotel Villa Marsili in Cortona, Italy

Hotel Villa Marsili is located about a block and a half from Cortona’s shopping and restaurant center. The hotel boasts dramatic panoramic views of both the Tuscan countryside and neighboring region of Umbria from its hillside location. We love the hotel’s front courtyard, and the beautiful rooms as well. Additionally, breakfast is included with your room, and offers staples such as breads, cold cuts, yogurt, fresh fruit, and coffee. Our favorite part of Villa Marsili (besides the view) are the people that work there — from the people working in the breakfast room to the front desk, employees are friendly and welcoming. Plus, those working at the front desk are always always eager to help you plan your day in Tuscany. Villa Marsili recently joined forces with the Best Western Signature hotel collection to ensure uniform quality and easier booking services, only adding to the hotel’s amenities.

Places to Eat in Cortona, Italy

  1. Trattoria Toscana: Located just uphill from Piazza Signorelli, Trattoria Toscana caters to a blend of locals and tourists. Our favorite meal was the Steak Florentine (massive T-bone steak, cooked with simple spices and sliced to share) and pasta. Make sure to try a dish with pici pasta while you are in Tuscany. Pici is a specialty of Tuscany, and is a hand rolled pasta (kind of like a thick spaghetti noodle). We loved how Trattoria Toscana prepared their daily special with pici: covered in tomato sauce and served with fresh mozzarella.
  2. Locanda al Pozzo Antico: Located on a side street below Via Nazionale, this restaurant offers a quaint atmosphere. Restaurant guests can choose to sit at tables out front, inside, or in a small courtyard. Plus, each meal is deliciously prepared based on traditional Tuscan recipes.
  3. Gelateria Snoopy: Named after Snoopy, the dog from the U.S. Peanut’s comics, this gelato place is fun to visit and offers the best gelato in town. Made fresh daily, there is a huge variety of flavors to sample and choose from. This gelato shop is located in Piazza Signorelli (behind the bell tower). We loved to grab our gelato and take it to sit on the steps of the bell tower. However, be warned – during the heavy tourist seasons, Snoopy’s runs out of some flavors in the evenings, so either go early to have your pick, or be adventurous!

Things to Do in Cortona, Italy

Via Nazionale, Cortona, Italy

Shop on Via Nazionale

Cortona’s main street offers a wide variety of small shops to pique your interest. From women’s clothing stores and shops filled with leather products (such as purses, belts, coats, and bags), to countless art galleries, you will be sure to find things to take home. Plus, most of the art galleries are familiar with shipping abroad, so don’t worry if you fall in love with a painting of the Tuscan countryside: it doesn’t have to fit in your bag!

Walk through the Park (and Visit Bramasole)

Piazza Garibaldi (the entrance of Via Nazionale as you come up from the hotel) leads to both the town center and town park. This tree lined park offers breathtaking views of Tuscany’s countryside, a playground for children, fountains, and a lovely gravel pathway. We especially loved walking through the park on hot summer afternoons or for after-dinner evening strolls.

Also, if you continue through the park, you will eventually reach a residential road. Follow this road and you will find Bramasole, the house that Frances Mayes bought which inspired the book and movie Under the Tuscan Sun. (This is the real Bramasole. The house that the film was taped in is located down the hill from Cortona’s old town.) Make sure to set your GPS to Bramasole if you visit to ensure you end up on the correct street and see the right house (there is a plaque on the gate to Bramasole so you will know when you reach it)!

Fountain in Cortona, Italy's tree-lined park
Basilica di Santa Margherita: Cortona, Italy

Visit the Basilica di Santa Margherita and the Franciscan Monastery

Located at the top of the hill, high above the town of Cortona, is a grand Roman Basilica and Monastery. While we drove up to visit these sites, but many people choose to hike the 0.8 kilometers uphill to visit from Cortona instead. In addition to enjoying the view from the top of the hill, visitors can tour the church and the monastery, marveling at the architecture, history, and importance of each.

Walk through the weekly farmers Market in Piazza Signorelli

As Cortona only has one small convenience grocery store, most locals get their groceries on Market Day. Everything from meat to vegetables to cheese is available at this market, which completely transforms Piazza Signorelli. Ask your hotel’s front desk for up-to-date information regarding when the markets are held.

Piazza Signorelli: Cotona, Italy
Italian Winery

Visit a Local Winery

Tuscany is home to the picture-perfect image of Italian wineries, and the wine industry is a major tourist draw for Tuscany. As such, make sure you tour a winery while you are in Tuscany! Ask your hotel for up-to-date information regarding which wineries are best to visit based on your preferences and interests.

Day Trips from Cortona, Italy

While you can take public transit to Cortona and other nearby towns, we prefer to rent a car when visiting to maximize our time. Here are a few of our favorite day trip destinations in the area:

Montepulciano is a nearby Tuscan town, and offers plenty of shops and winding cobblestone streets to explore. 

Montepulciano: Tuscany, Italy

Orvieto, located in the nearby region of Umbria, is also a walled hilltop town, but is much larger than Cortona, and thus offers a wide variety of shopping options as well as architectural wonders to wander through (from the large Cathedral in town to medieval stone buildings in the town center). 

Florence is one of Italy’s most famous cities. While you can drive there, we suggest driving down the hill from Cortona to Camucia, and then taking a direct train into the city. While in Florence, visit the Medici Palace, see Michelangelo’s David sculpture, stop by the famous Duomo (Cathedral) to see its famous dome roof, walk across the jewelry store lined Ponte Vecchio bridge, and shop in the famous high fashion stores (or tourist shops if you’re like us). Plus, grab a gelato and stroll along the city’s winding streets to gain a better understanding of Florence.

Florence, Italy (from Ponte Vecchio Bridge)