I am completely in love with Italy. From the canals of Venice, to the bright cliff-side buildings of Cinque Terre, to Rome’s ancient architecture and Sicily’s turquoise beaches, this country just holds a massive piece of my heart. And I believe the beautiful hill towns of Tuscany are a must on any Italian itinerary, and so when I recently got the chance to spend a week in Cortona, I was IN.
Cortona is one of the quintessential Tuscan hill towns. It is on a serious hill, and commands sweeping views over Lake Trasimeno and the plain of the Valdichiana (Chiana Valley). It has an insane amount of history packed into its tiny area, an interesting art scene, amazing food, and more.
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Legend has that Cortona was founded by Dardanus, the founder of Troy…specifically, he lost his helmet on Cortona’s hill and so the town took its name from that (corito). The Etruscans built the first town walls in the 4th century BCE, and the town became an important player in the area for centuries to come. It wasn’t until the Middle Ages that Cortona’s fortunes waned. Now it’s a remarkably well-preserved and delightful example of an ancient hill town.
I’ll be honest, I was worried about Cortona feeling too touristy and overcrowded, but didn’t experience that at all. Some tourist groups came through on occasion during the day, but not once in my entire stay did I feel like it was annoying or crowded.
How to get to Cortona
Rome, Pisa, Florence, and Perugia are the closest airports to Cortona…ranging from 58 kilometers (Perugia) to 320 kilometers (Rome). From there, you can choose to either drive, take a taxi, or take the train.
Driving is easy if you’re planning to do a lot of other driving, or take lots of day trips from Cortona. You just can’t bring the car inside the Cortona city walls. If you’re looking to arrange a driver to pick you up from the airport, this website has all the info you need on that as well as other transportation options.
I had spent a couple days in Rome, and so took the train out to the Camuccia-Cortona station. The trip is about 2.5 hours one-way and it’s super easy! One word of warning: the train platform at Roma Termini that goes to Cortona was like 300 meters past all the others. I didn’t realize that, and so ended up racing, dragging my bag, and pouring sweat to make the train. Once you arrive at the Camuccia-Cortona station, it’s a 10-minute drive up to Cortona proper. You can see train timetables on Trenitalia’s website.
Pro tip: If you take the train, pre-arrange for a taxi before you arrive, since they don’t just sit around.
Getting around once you’re there
Very few cars are allowed inside the city walls, and those are almost entirely locals. If you do bring your own car, you’ll need to park in one of the main lots outside the town walls and get around by foot inside. I was fortunate that the taxi driver who picked me up at the train station has permission to drive in the town walls, so he dropped me (and my luggage) off at my apartment…but I had to drag all my luggage down when I left.
What to do in Cortona
There are actually a lot of things to do, including museums, tons of shopping, art galleries, historic churches, and gobs of ancient Etruscan history, if all that’s your thing. (Side note, I have like…Etruscan PTSD from a super intense senior-level ancient Roman history class I took at 8am first semester of my freshman year of college. It’s like mentioning “Etruscan” will give me a twitch…)
But to me, the best part is less about going to a particular museum or taking a specific day trip (though they’re both great). It’s wandering, taking pictures of beautiful details, learning about the history, talking to the locals, and sampling all the amazing restaurants in town.
Wander and look for charming details
If you did nothing else, this is THE BEST thing to do in Cortona. The town’s narrow and steep little streets and alleyways are jam-packed with beautiful touches…whether colorful doors, lots of plants, bright pottery, decorative fountains, or a myriad of other things.
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If you pay attention, even the walls of the alleys have something to say…
One thing that’s hard to truly showcase in photos is how insanely steep the streets of Cortona are. I mean…I’ve spent time in hill towns, but nothing like this. A couple of the doorway pics below start to give you a sense of the angle we’re talking about.
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So, speaking of crazy hills and angles, let’s take it to the extreme…
Climb up to the Fortress Girifalco & Santa Margherita
Google Maps got me on my way, though there are a few signs here and there. It is quite a climb up there, but definitely worth it.
The church of Santa Margherita is the first thing you’ll come upon. Built in the 1300s, it’s dedicated to Santa Margherita, the patron saint of of Cortona…as well as a whole host of other things. The falsely accused, hoboes, the insane, reformed prostitutes, and a lot more. Her remains are on full display if that’s of interest to you.
I can’t tell if the building here is the original one, but it’s very striking nonetheless. I didn’t end up going in due to time, but now I’m bummed because based on the pics I’m seeing it is super colorful and interesting inside.
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A fortress of some type has probably been standing in this spot since about the 5th or 6th century BCE, courtesy of the ancient Etruscans. Something more like the current iteration likely took shape in the 13th century AD, and then the unique pentagonal-shaped courtyard dates back to the 1500s when they connected the fortress to the town walls.
One little more modern history tidbit I found interesting is that WWII it housed 250 children whose parents were exiled abroad and served as an observation post for German radio operators. Eventually it was put to use accommodating liberation troops from the Allied forces.
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You can check the opening times on the official website, and it usually costs €5 to enter. There’s a little gift shop there with some local crafts (I bought a beautiful tea mug for my mom), and then you can wander around the fortress. I’ll speak more on it towards the end, but make sure to check out the Bistrot for lunch, a snack, or a glass of wine.
Cortona is very into the arts, and so you’ll often find some art gallery displays in the fortress—and throughout the town as well. I’m not a huge art person myself, but appreciate the ambiance it adds…I was more into the views! One a pretty day you can’t beat these views of the valley.
People watch in the Piazza della Republica
This is really the beating heart of Cortona. I loved sitting inside the Bar Signorelli in the morning and having my coffees and pastries (yes, plural, don’t judge…), but also having a glass of wine at one of their outside tables in the afternoon.
With a view of Palazzo Comunale, you can see not only some tourists, but all the locals taking their passeggiata in the late afternoon and through the evening. They greet each other, stop to chat, with kids running around and playing. People pop into stores, grab a glass of wine. It is the perfect picture of a small Italian community.
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There are sometimes flag demonstrations the town puts on…it reminded me of American homecoming, with the drumlines, the flying flags, marching, costumes, and more 🙂
Other main areas to explore
The Piazza Signorelli is right around the corner, and another great place to sit with some wine or coffee. You can see the Teatro Signorelli there, which was built in the mid-1800s. It’s hosted many cultural events, and you should check the schedule for a concert, show, or something else. If nothing else, walk through and take in the inside of the theatre.
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From the Piazza della Republica, meander down the Via Nazionale. This is the main shopping thoroughfare, full of leather, handcrafts, pottery, art, foodstuffs, bars and restaurants, and so much more. If you walk to the end of the road, you hit Piazza Garibaldi
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Don’t forget your twice-daily gelato prescription!
Rent an amazing apartment with a view
If you’re staying in a hill town, you’d be crazy not to pick a hotel or rental with a view. I rented Giampero’s “I Terrazzini” apartment on Airbnb and was thoroughly CHARMED. It was absolutely perfect. I’ve written a whole post about my stay here!
(As an Airbnb Associate, I earn a small amount when you book through this link, at no cost to you).
I enjoyed beautiful quiet foggy sunrises, bright blue-skied days, and SUNSETS. The sunsets were a major selling point for this apartment, and they didn’t disappoint. I tried to spend almost every evening up here watching the sunset before heading down for my dinner reservations.
I loved how the rich green valley spread out below, with Lake Trasimeno in the distance and the Church of Santa Maria delle Grazie nestled at the base of the hill. Then the bright oranges and pinks took over and I couldn’t take my eyes off the clouds.
*SIGH* It was hard to want to come down off my hilltop…
Walk to Villa Bramasole (the “Under the Tuscan Sun” house)
Full disclosure: I’ve never watched or read “Under the Tuscan Sun”, so this didn’t really mean much to me. But on my next-to-last day I felt like I needed to go do something that didn’t entail pastries or wine. My knee issue had made me much less exploratory than I’d planned. So I decided to try going out to Villa Bramasole.
I used Google Maps to help me get there. The path is not marked at all, so you kind of have to go with your gut and use Google Maps to help course-correct. The official Cortona site has these instructions, if they’re helpful. Unfortunately it was a dumb choice for me, as my knee got worse and worse throughout the walk, to the point where I thought I was going to black out a few times. So I don’t have fond memories of this walk 🙂
It’s a fine walk if you’re not in pain though. Is it a must-do in my opinion?? No.
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Visit a winery in nearby Montepulciano
Just a very short drive from Cortona are many of Italy’s most well-regarded wine areas, including Montepulciano, Chianti, and Umbria. A winery tour and tasting is a must when visiting this area. About 15 of us did a small group trip to Tenimenti d’Alessandro. I wish I’d just come on my own because I think the service and experience would have been much better.
The grounds are beautiful and food and wine delicious. We just got a lackluster tour and they didn’t really spend any time explaining the wines, why they paired them with the food, what flavors we should get out of them, etc. I think the people that came on their own vs. in a special group tour had a better experience.
Where to eat and drink in Cortona
I’ve written a much deeper post on Cortona’s food scene, so will just provide an overview here. Cortona is a foodie’s PARADISE! It’s shocking how many amazing restaurants there are for a town this size. From what I understand, it’s because the locals themselves are foodies and really enjoy eating out.
First, let’s talk your morning coffee routine. I tried a few different places for my cappuccino and cornetto (or cappuccini and cornetti, because let’s face it, it was *always* multiple…), and quickly settled into a routine at Bar Signorelli. It was definitely my favorite place to sit and sip my coffee, nibble on a pastry, and read my Kindle for a bit. I enjoyed watching the locals come in for their quickly-downed coffee at the bar, and the owner and staff there were incredibly friendly and welcoming to me.
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In terms of lunch and dinner, it’s hard to even know where to start! One of my absolute favorite meals was actually the lunch I enjoyed at La Loggetta. It sits right overlooking the main square, with an amazing view from the patio. The menu was really interesting, and the food was exceptional from start to finish…from the risotto with licorice and forest fruits to the tart with fig preserves and walnuts.
A few other restaurants you definitely need to try out…
- Osteria del Teatro, where I had truffle fondue and a crisp Vermentino wine, along with two delicious pasta dishes for my dinner
- Ristorante Preludio, where I got to sit at an adorable little table-for-one overlooking everyone else, and dine on cheese souffle with pear compote and black truffle
- La Bucaccia, tucked down one of the crazy steep little streets, where I stuffed myself with an amazing cheese souffle (sformatino), some kind of chestnut ravioli with porcini, steak, and zuppa inglese
- Trattoria Croce del Travaglio , with simple and delicious pizza. While I’m more partial to Naples-style Italian pizza vs. this very thin cracker-like crust, this really hit the spot
- Bottega Baracchi, right at the end of Via Nazionale overlooking Piazza Garibaldi. While it has a patio for drinks, I ate down in the cave-like dining room and loved the ambiance and the interesting food options
- Bistrot at Fortezza Girifalco, the cafe at the fortress, is a lovely option for a snack, lunch, or just to sit and have a coffee or drink
If you’re just looking to sit and have a drink, there are tons of great options. I’ve already mentioned Bar Signorelli, and having a drink on the patio of La Loggetta is a great option too. Caffe Tuscher and Bottega Baracchi are favorites among the locals. Head up to the fortress and watch the sunset with a drink
Yeah…I may have gained some weight while visiting Cortona! #totallyworthit
Tips for enjoying your visit to Cortona
A few other notes for planning your stay in Cortona…
- Molesini’s Market is a grocery store right in the Piazza della Republica. It’s quite well-stocked and has everything you need. There’s a gastronomia next door (attached) that makes a delicious panino for like 3 euros. They also have an incredibly diverse wine offering in across the piazza at a wine store of the same name.
- The restaurants in Cortona are amazing, but you do really need to make reservations at most places!
- Cellphone signal is terrible throughout Cortona, due to all the thick stone walls. It’s really important that you have good access to wifi wherever you’re staying.
- I cannot stress this enough—Cortona is NOT a great place for people with mobility issues. The streets are incredibly steep, there are stairs everywhere, super wobbly cobblestones…it’s a handicapped or injured person’s nightmare. I had a particularly upclose experience with this since my knee was excruciating the whole time, and just trying to get around was super discouraging and painful.
If you can’t tell, I adored my time in Cortona, and would return in a heartbeat! What questions did I not answer that would be helpful as you plan your own trip?? Hit me up in the comments!
Other dreamy medieval and hill towns you’ll love:
- Exploring the Hill Towns of Northern Croatia
- The Medieval Charms of Kilkenny, Ireland
- 9 Reasons You Will Fall in Love with St. Paul-de-Vence, France
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