What One Day in Cortona Looks Like

Things to Do in Cortona in a Day

Wander Cortona’s Old Town

Cortona’s old town is a highlight of any visit, with its narrow cobblestone streets, stone homes, and unique shops that feel straight out of a postcard. It’s the kind of place where you’ll want to get lost—and we certainly did.

As we wandered the residential streets, every turn brought something unexpected, from hidden courtyards to scenic alleyways. Locals, including friendly Nonnas, chatted outside their homes and offered warm smiles as we passed by.

We also noticed many cats lounging in the sun or strolling about. Most of them gathered near the Convento di San Francesco, where a fascinating relic of St. Francis of Assisi, the patron saint of animals, is kept. The connection felt fitting and added a special touch to our exploration.

Admire Piazza della Repubblica

Piazza della Repubblica is the heart of Cortona and is impossible to miss during your walk through the old town. Its focal point is the Palazzo Comunale di Cortona, with its striking clock tower and grand steps that invite you to take in the view from above.

The piazza is a perfect spot to grab a coffee or find a seat to soak in the vibrant atmosphere of one of Italy’s most beautiful towns. As you stand in the middle of the square, it’s remarkable to think that it has been part of Cortona since Etruscan times—long before the Roman Empire or the birth of Jesus.

From here, choose one of the narrow streets leading off the square. Each path promises a stunning view or a hidden gem worth discovering.

For fans of Under the Tuscan Sun, this is where Diane Lane’s character shops at the outdoor market, buys grapes, and spots the blonde woman holding the duck. It’s a fun little nod to the movie that adds to the charm of the experience.

Visit Piazza Signorelli

Italian piazzas are always a highlight, and Piazza Signorelli is no exception. This small, charming square is just around the corner from Piazza della Repubblica, so you’re bound to pass through it as you explore Cortona.

On our visit, we strolled through it a couple of times before realizing it was the setting for the fountain scene in Under the Tuscan Sun. While the fountain was a prop created for the movie, it adds a fun, cinematic connection to the square.

However, Piazza Signorelli’s real story goes much deeper. Once the headquarters of the Florentine rulers of Cortona, it has a history tied to the town’s governance and culture. It’s named after Luca Signorelli (1445–1523), a Renaissance master best known for his frescoes of the Apocalypse and the Last Judgment in the Cathedral of Orvieto.

Surrounding the piazza, you’ll find the striking Signorelli Theatre, the Municipal Palace, and the historic Casali Palace—all worth admiring as you take in the square’s rich history and vibrant energy.

Shop Along the Via Nazionale

If there’s one street you shouldn’t miss in Cortona, it’s Via Nazionale. While some shops may seem aimed at tourists, you’ll find plenty of authentic treasures here.

The specialty food stores are a highlight. At Marfuga Shop, we sampled their award-winning olive oil and couldn’t resist buying two bottles, along with some decadent truffle butter. The friendly shop attendant even went above and beyond by recommending and securing a reservation at her favorite local restaurant.

We also visited a leather shop where we picked up a handcrafted belt and a gorgeous leather backpack. Along the way, we stumbled upon art galleries featuring unique, handmade pieces by talented local artists.

Eat Gelato at Dolce Vita

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While at the olive oil shop, we got a great tip: try the artisanal gelato at Dolce Vita, especially their fresh olive oil gelato made with Mafuga’s award-winning oil. Naturally, we couldn’t pass that up.

Keep in mind that olive oil gelato may not be available year-round since the flavors rotate with the seasons. Regardless, Dolce Vita’s gelato is some of the best we’ve had.

Don’t leave Cortona without treating yourself to a scoop (or two). After all, no day in Cortona—or anywhere in Italy—is complete without gelato.

Convento di San Francesco

During our day in Cortona, we stumbled upon the Convento di San Francesco, a smaller but fascinating church tucked away in town.

Inside, you’ll find two relics of St. Francis of Assisi: the tunic he wore at his death and the cushion that supported his head during his funeral. As the patron saint of animals, it felt fitting to see so many cats lounging around the area near the church, adding a charming touch to our visit.

If you visit in the afternoon, be sure to step inside. When the sunlight streams through the stained-glass window, it casts a striking red cross on the wall—a serene experience.

Optional: Duomo di Cortona

If time allows during your one day in Cortona, consider visiting the Duomo di Cortona, also known as the Cathedral of Santa Maria Assunta. Located in Piazza Duomo, a lovely square with restaurants and cafés, this historic site is one of the oldest churches in Tuscany.

The Duomo’s origins date back to the 11th century when it was a Roman temple before being destroyed and rebuilt. Over the centuries, it has undergone several restorations, the most recent in the 18th century, which shaped much of its current appearance.

Inside, you’ll find remarkable works of art, including Pietro da Cortona’s Adoration of the Shepherds, making it a worthwhile stop for art and history enthusiasts.

Visit the MAEC – Museum of the Etruscan Academy

For history buffs, the MAEC (Museum of the Etruscan Academy) is a must-see and one of the top things to do in Cortona. As one of Tuscany’s most significant Etruscan museums, it offers a fascinating glimpse into ancient history.

The museum houses an extensive collection of Etruscan and Roman artifacts, along with historical exhibits and art pieces. With four floors to explore, it’s a treasure trove of archaeology and culture, making it a rewarding stop during your day in Cortona.

Tour Ideas:
Cortona Private Walking Tour [book here]
Easy Guided E-bike Tour Around Cortona [book here]
Dining Experience at a local’s Home in Cortona [book here]

Where to Eat in Cortona

Cortona is brimming with fantastic restaurants, and we had the pleasure of enjoying two during our one day in Cortona. While finding a spot for lunch is easy, dinner is a different story—reservations are highly recommended.

Thankfully, a friendly local shopkeeper insisted we try one of her favorite places and even called ahead to secure us a table. Without her help, we might have been turned away!

Located in the heart of the old town, Trattoria Dardano is a family-owned Tuscan trattoria that’s as cozy as it is authentic. For lunch, we were seated among locals—a promising sign—and found ourselves so captivated by their dishes that we ordered the same.

We tried the Pappardelle al Cinghiale (wild boar) and Pici all’Anatra (duck ragù), both of which were outstanding. The pasta was fresh and perfectly cooked, with hearty, savory, deeply satisfying flavors. It was the kind of meal that fulfilled the hearts in our stomachs.

For dessert, we shared a budino al cioccolato, a chocolate pudding similar to panna cotta but made with Nutella. Usually, we’re not big fans of panna cotta, but this was different—light, creamy, and rich. Needless to say, we didn’t leave a single bite behind.

To top it all off, the price was a pleasant surprise—less than 30 euros for two entrees, dessert, and a glass of wine. With delicious food, reasonable prices, and excellent service, Trattoria Dardano is a must-visit in Cortona.

For dinner, we visited Osteria Le Rughe di Cortona, a recommendation from the same friendly local who sold us olive oil earlier in the day. She was so enthusiastic about this spot that she called and begged the restaurant to seat us, even if it meant dining a bit earlier than usual.

Tucked away on a quiet sidestreet you might otherwise miss, Osteria Le Rughe di Cortona is a small, unassuming gem. The local shopkeeper had raved about their crostata Toscana—technically crostini neri (black crostini) with chicken liver pâté—claiming it was the best in town. While we skipped it (liver just isn’t our thing), her passion for the dish was infectious, and it’s worth trying if you’re adventurous.

Instead, we opted for the night’s special: steak with porcini mushrooms (in season) and a side of rapini. It turned out to be one of the best meals of our trip. The steak was perfectly cooked, tender, and perfectly seasoned, while the porcini mushrooms were rich and flavorful. A rare treat for us, the rapini made a delicious complement to the main course.

Pro tip: Always ask about the specials. They often highlight the freshest, in-season ingredients and are the standout dishes.

While we started dining early, the restaurant quickly filled with locals by the time we left, a sure sign of its quality. Reservations are highly recommended to secure a table at this cozy osteria.

How to Get to Cortona, Italy

Planning your day trip to Cortona requires some thought about transportation, as it’s not as simple as hopping off a train like in Florence, Rome, or Bologna. While it takes a little extra effort, the journey is worth it.

FAQs About One Day in Cortona, Italy

Is Cortona a good base for Tuscany?

Yes, Cortona can be an excellent base for exploring Tuscany. It’s centrally located and within an hour’s drive of cities like Siena, Arezzo, and Perugia. Its proximity to nearby towns such as Montepulciano and Chiusi also makes it ideal for day trips while enjoying the charm of a smaller town.

Find and Book Accommodations in Cortona