ong before Frances Mayes put it on the international map with “Under the Tuscan Sun,” Cortona was already one of the most quietly captivating towns in Italy. The Etruscans settled here nearly 3,000 years ago, building massive stone walls that still wrap around the hillside today. The Romans came next, then the medieval lords, and then the Renaissance, each layer adding something to a town that feels less like a museum and more like a place that has simply never stopped being interesting.
What Mayes captured — and what draws people here from all over the world — is the atmosphere. Cortona is steep, intimate, and deeply Tuscan in a way that the bigger, more famous towns sometimes aren’t. There are no tour bus parking lots. No selfie stick vendors. Just stone streets climbing the hillside, vine-covered terraces overlooking the Val di Chiana, and a quality of light that makes everything look like a painting.
The drive from Rome
Cortona is one of the closest Tuscan destinations from Rome — about 2 hours by car, heading north on the A1 autostrada and exiting at Valdichiana. The last stretch of road, climbing from the flat valley floor up to the town perched on the hillside, is stunning.
There is a train station at Camucia-Cortona, down in the valley. Trains from Rome take around 2 hours with a change in Terontola. From the station, it’s a 15-minute taxi or bus ride up to the old town. It works, but it’s not seamless — and you lose time on the connections.
A private transfer brings you right to the town gate. No connections, no uphill taxis, no luggage hassle. And if you’re doing a day trip from Rome, the flexibility of having your own driver means you can combine Cortona with other nearby destinations and make a proper day of it.
What to do in Cortona
Cortona is small enough to explore on foot in a few hours, but the kind of place where you’ll want to linger.
Start at Piazza della Repubblica, the main square, where the 13th-century Palazzo Comunale overlooks a cluster of cafes and shops. From here, wander uphill through the steep alleys — every turn reveals another view over the valley below. The higher you climb, the better the panoramas, all the way up to the Basilica di Santa Margherita and the Medici Fortress at the very top.
The MAEC (Museo dell’Accademia Etrusca e della Città di Cortona) is genuinely worth an hour. The Etruscan collection includes an extraordinary bronze chandelier from the 4th century BC — one of the most significant Etruscan artifacts ever found — along with ceramics, jewelry, and funeral objects that illuminate a civilization most people know little about.
For something quieter, walk down the hill to the church of Santa Maria delle Grazie al Calcinaio, a Renaissance gem by Francesco di Giorgio Martini that sits alone among olive groves below the town. It’s a 20-minute walk, and the setting is peaceful enough to justify the detour.
And then there’s the food. Cortona’s restaurants tend to be unpretentious and excellent — the kind of places with handwritten daily menus, local wine by the carafe, and ribollita (Tuscan bread soup) made the way it’s been made here for generations. Your driver will know which places are genuinely good and which are coasting on a nice terrace view.
“Under the Tuscan Sun” spots
If you’ve read the book or seen the film, you’ll recognize the atmosphere more than specific locations — but there are a few landmarks. The Bramasole villa (Mayes’ real house) is on the outskirts of town, visible from the road but privately owned and not open to visitors. The town square, the views, and the general feel of Cortona’s daily life are all authentically captured in the book, and walking around you’ll have plenty of “that’s the Tuscany she was writing about” moments.
Combining Cortona with other destinations
Cortona sits at the eastern edge of Tuscany, right on the border with Umbria, which opens up some interesting combinations:
Cortona and Montepulciano — about 30 minutes apart. This is one of the best one-two punches in southern Tuscany: Cortona for the culture and atmosphere, Montepulciano for the wine and food.
Cortona and Pienza — roughly 45 minutes. Add pecorino cheese and Val d’Orcia views to your Cortona day.
Cortona and Lake Trasimeno — just 20 minutes north. The largest lake in central Italy, with a tranquil, undiscovered feel. Nice for a lunch stop at one of the lakeside towns like Castiglione del Lago.
Cortona and Arezzo — about 30 minutes. If you loved the film “Life is Beautiful,” Arezzo’s Piazza Grande is where much of it was filmed. The town also has a phenomenal Piero della Francesca fresco cycle in the Basilica di San Francesco.
Practical information
Cortona is steep. Seriously steep. Comfortable shoes are essential, and anyone with mobility concerns should know that the main square is about halfway up the hill, with the major attractions spread above and below it. Your driver can drop you as close to the center as possible, and there are a couple of gentler routes through town that avoid the steepest streets.
Allow 2 to 3 hours for a comfortable visit to Cortona itself. If you’re combining it with another town and a winery stop, plan for a full day.
Our Mercedes E-Class and V-Class vehicles are available for both day trips and one-way transfers to Cortona. Book your transfer or reach us on WhatsApp at +39 333 283 1963 — we’re happy to help you plan the perfect day. See our full Rome to Tuscany transfers guide for all available routes.