Cortona, Italy Travel Guide: A Day in the Real Under the Tuscan Sun Town

Our first trip to Italy was a New Year's trip to Cortona, booked a couple of years before we actually moved here. If we're honest about why we picked it, it's the same reason a lot of women in their 40s and 50s end up in Cortona: we'd both watched Under the Tuscan Sun more times than we'd like to admit and wanted to see if the place was real. It was, just not in the way the movie tells it.

At one point on that trip, I looked at Lisa and asked if I should just take a bag of money and buy a house. There was no bag of money. It was wine talking, and the view. We didn't buy anything, but we did fall completely in love with Italy. Looking back, that weekend was probably the moment everything changed. A couple of years later we packed up our lives and moved to Tuscany for real.

If you're looking for the real Under the Tuscan Sun town, here's exactly how we'd spend one perfect day in Cortona.

Best Tours & Experiences in Cortona

Planning to explore beyond wandering the historic streets? Browse the top-rated tours, wine tastings and day trips available in and around Cortona.

Cortona feels different from most Tuscan hill towns we've been to. It's small enough that you don't need a map, and it never feels staged for tourists the way some of the more famous stops can. We've been back several times over the years, and every trip ends the same way: we tell ourselves we'll only stay for lunch, and then it's late afternoon and we're still parked in one of the two piazzas arguing about whether to order another glass of wine.

If you're planning a Tuscany road trip, we'd pair Cortona with Montepulciano. They couldn't feel more different, but together they make one of our favorite day trips in the region.

Best Things to Do in Cortona

You don't really need a checklist for Cortona. Most of the fun is just walking the streets and stopping wherever something catches your eye. That said, these are the places we'd never skip.

Two Piazzas, One Really Good Meal

Everything in Cortona happens between two piazzas. One holds the Duomo and a handful of restaurants with outdoor terraces. The other, Piazza della Repubblica, is where locals actually gather: cafés spill onto the square, and it's where you'll end up whether you planned to or not. Two piazzas and the street connecting them is basically the whole old town, which is part of why one day here is enough.

See the Real Under the Tuscan Sun

Frances Mayes wasn't looking for a book deal when she bought Bramasole in 1990. She saw a wrecked farmhouse on a hillside outside town, made an offer, and spent years fixing it up before any of us had heard her name. The memoir came after that, then the movie in 2003 with Diane Lane playing a version of her. They shot the market scene right in Piazza della Repubblica, which is why it looks so familiar the first time you walk through it. What gets us is that Mayes is still around town most of the year. Not doing press, not running tours. Just a neighbor who happens to have written a very famous book.

Eat an Amazing Lunch

One of the best meals we've had anywhere in Italy happened at Ristorante La Loggetta, tucked on the quieter piazza beside the Cathedral of Santa Maria Assunta. It was so good that years later we brought Lisa's sister and her husband back to the same table, and it held up completely, which almost never happens on a repeat visit. If you do one thing in Cortona besides wandering, make it a long lunch at Ristorante La Loggetta.

Don't Skip Snoopy Gelateria

Just behind the cathedral is Snoopy, a tiny gelateria that's become one of our traditions. Lunch, a slow walk, then gelato, in that order, pretty much every time. We always say we're leaving after one scoop. We rarely do.

Take in the Views

Being up this high above the Val di Chiana does something to the view. Half the side streets in Cortona just stop at a railing and drop straight down into vineyards and olive groves. We've never quite gotten used to it, even after all these visits. If you're coming from Florence or Siena, this is usually the first place Tuscany starts looking like the postcard version people have in their heads before they land.

Explore Cortona's Etruscan History

Rome gets all the credit for ancient history in Italy, but Cortona was doing its own thing as an Etruscan city long before Rome mattered. You don't have to plan around it. The MAEC museum is there if you want an hour indoors, and otherwise the old city walls and scattered ruins just show up while you're walking to lunch.

Girifalco Fortress and Basilica di Santa Margherita

We hiked up to Girifalco Fortress with Cash, and it wasn't the brutal climb we'd braced for. We didn't go inside, but the views from up there are beautiful, even if the trees block a good chunk of the town itself, which surprised us. Cosimo I had the fortress built in 1556 on top of an older medieval fort, which itself replaced an Etruscan structure, so there's history stacked on history under those four bastions. On the way up, you'll pass the Basilica di Santa Margherita, built on the site where Cortona's patron saint spent her final years and where she's buried. The current building is mostly a 19th-century rebuild, but the site itself dates back to the 1200s.

Le Celle Hermitage

We've driven past Le Celle several times and never actually stopped, which is probably the more common way people experience it than they'd admit. It's a small hermitage just outside town, founded around 1211, that briefly housed Saint Francis of Assisi himself. The Franciscans built out a sanctuary and a handful of monk cells there in 1235, and Capuchin friars have lived on the site since the 1500s. It's on our list for next time.

Getting There

By Car

Car is genuinely the easiest way in, and it's what we'd recommend if you're already road-tripping through Tuscany. Parking is outside the walls, and everything in the old town is a walk from there.

By Train

There's a direct train from Florence to Camucia-Cortona, running roughly hourly and taking just under two hours. The station itself is about 3 km from the historic center, so you'll still need a taxi, a local bus, or a fifteen-minute uphill walk to actually reach town.

By Bus

Autolinee Toscane runs a bus from Camucia to Florence a few times a week, similar travel time to the train, just cheaper. Once you're at the Camucia station, local Etruria Mobilità buses run from the square out front into central Cortona.

Places to Visit Near Cortona

Pair Cortona with Montepulciano if you want two very different hill towns in one trip: ours, versus one built entirely around wine tasting. Arezzo is close enough for a second stop the same day if you're not in a rush. And if you're curious about Umbria without actually crossing the border for long, Lake Trasimeno is visible from parts of Cortona and makes an easy add-on if you have a car.

Know Before You Go

Best time to visit: Spring and fall are ideal. Autumn is especially beautiful during olive harvest, and summer brings lively cafés without feeling as crowded as Siena or San Gimignano.

How to get there: A car is easiest. You can also take a train to Camucia-Cortona, then a bus or taxi into the historic center.

Time needed: One full day is enough.

Walkability: Excellent, but steep, with plenty of cobblestones.

Need a car? Recommended if you're exploring more of Tuscany.

Pair it with: Montepulciano, Lake Trasimeno, or Arezzo.

Frequently Asked Questions

Is Cortona worth visiting? Yes. It's one of our favorite hill towns in Tuscany, an easy day trip from Florence, Siena, or Montepulciano, and worth it even if you've never seen Under the Tuscan Sun.

Was Under the Tuscan Sun filmed in Cortona? Yes. Several scenes, including the market scene in Piazza della Repubblica, were filmed here, though the production shot other parts of the movie elsewhere in Italy.

Can you visit Bramasole? No. It's a private home and isn't open to visitors.

Is one day enough for Cortona? Yes. The old town is small enough to see fully in a day, with time left over for a long lunch.

Can you reach Cortona by train? Yes, technically. Trains stop at Camucia-Cortona, about 3 km from the historic center, so you'll still need a taxi or local bus for the last stretch uphill.

Planning More Tuscany Travel

If you're road-tripping through Tuscany, we'd also recommend our guides to Montepulciano, Montalcino, Siena and San Gimignano. Each town has its own personality and together they make one of our favorite regions in Italy to explore.