Touring Tuscan Towns – Cortona

Are you traveling to Tuscany, and wondering what wonderful towns you need to add to your must-see list? Well, I have a great option for you, the hilltop town of Cortona. This stone-clad town features a magnificent medieval tower, a busy piazza and endless winding alleyways. As a romantic at heart, I fell in love with Under the Tuscan Sun, first the book by Francis Mayes, and then the movie which put this town on the map; and for good reason!

One of my favourite scenes in the movie has to be her writing the postcard while sitting on the ledge overlooking the piazza. 

“Dear Mom. It’s market day in Cortona. The piazza is an ongoing party, and everyone is invited. Clichés converge at this navel of the world. You almost want to laugh, but you can’t help feeling these Italians know more about having fun than we do.

I eat a hot grape from the market, and the violet sweetness breaks open in my mouth. It even smells purple.

I wish I could stay longer, but the bell reminds me of time. ‘Ding-dang-dong,’ the bell says, instead of ‘ding-dong.’ I wish you were here.


The historic and beautiful Tuscan Town of Cortona. A hilltop town in Italy.
Me, the Holidaymaker, sitting on the same ledge overlooking the piazza waiting for the Ding-dang-dong chimes of the clocktower

Let’s take a tour of Cortona, shall we?

The Piazza

The main piazza in Cortona, a small town in Tuscany, Italy

The main square, called Piazza della Repubblica, features many historical buildings dating back to the 13th century. A well-preserved town hall, clock tower and former palace are just some of the significant landmarks you will find. 

This is a lively piazza, the very heart of this beautiful town. It’s where you will find the locals constantly coming and going, catching up with one another and stopping in on their favourite shops. And, there are many, many wonderful shops. Everything from art to antiques to jewelry to leather. Not to mention the cafés and restaurants.

The main piazza in Cortona, a small town in Tuscany, Italy

The Streets of Cortona

The historic and beautiful Tuscan Town of Cortona. A hilltop town in Italy.

Cortona’s streets are steep. You will be going up and down as you make your way through the town. All but one, the main Via Nazionale (linking’ Piazza Garibaldi and Piazza della Repubblica) together. You might hear locals refer to it as Ruga Piana (or flat street).

A couple streets worth seeking out is Via Guelfa and Via Ghibellina. These are the two original streets of the old town. 

Pin on Under the Tuscan Sun

Lastly, find Via Janelli. It’s a picturesque thoroughfare of 14th-century timber-framed houses. These ancient medieval houses are built of stone and brick, while the jambs, the thresholds and the architraves are exclusively in stone. The upper floors of the house project onto the street and are supported by wooden shelves.

The Etruscan Walls

The historic and beautiful Tuscan Town of Cortona. A hilltop town in Italy.

Cortona is believed to have been a powerful Etruscan town during period of 400-600 BC. Then in the 13th century it became a city state with its own currency. It was owned by the Medici family and remained under their rule until 1737. Following the Italian Wars of Independence, Cortona became part of the Kingdom of Italy.

The historic and beautiful Tuscan Town of Cortona. A hilltop town in Italy.

The Etruscan walls are incorporated into the medieval walls that surround the historic center. Inside the walls, you can wander the narrow medieval streets often getting glimpses of the wonderful views of the valley below.

The Views

The beautiful Tuscan views from Cortona, Italy
The hilltop views of the Val di

Cortona is situated on a hill (500 meters above sea level), where you can enjoy a unique and amazing view of the Val di Chiana. It lies in the eastern part of Tuscany, in the Arezzo region, very close to border of the Umbria region and Lake Trasimeno. In such close proximity to other wonderful Tuscan towns this makes for a great area to explore.  

The beautiful Tuscan views from Cortona, Italy
The hilltop views of Cortona looking to the valley below with Lake Trasimeno in the distance.

The Churches

Cortona, can be found in the Tuscan region of Italy. A lovely small town that features many beautiful churches
This is the Cortona Cathedral (or Duomo). A Renaissance cathedral, built on the site of an Etruscan temple. It features a has an 11th-century façade, as well as, 16th to 17th century paintings inside.

San Francesco church built in the 13th century

Cortona, a small town in Tuscany Italy is definitely worth having on your must-see list
San Domenico church built in the 15th century
The Santa Maria del Calcinaio in Cortona Italy. This beautiful Renaissance church dates back to the 14th century.
Lastly, my favourite. On your way to or from Cortona, along a twisting road you will come upon this beautiful Renaissance church. The Santa Maria del Calcinaio. It was built in 1513, and is one of the most architecturally important Renaissance churches in all of Tuscany.

The Museums

Visit the small Museo Diocesano across the piazza features a superb art collection. It depicts the town’s history from the 3rd century to the 18th century. 

Wander the fascinating Museo Etruscan Museum displays artifacts from Etruscan and Roman era.

Take a look at the Etruscan Tombs found at the foot of the town. Here you will see the Etruscan tombs dating back to the 3rd century BC.                             

The Girifalco Fortress overlooking Cortona dates back to 5th or 6th century. The fortress walls connect to the town walls and creates this a pentagonal-shaped, internal courtyard.             

Where to Drink and Dine

The best gelato: Gelateria Snoopy 

Visit the best wine bar (and shop): Enoteca Molesini 

For the best coffee:  Café Tuscher

And, the best alfresco dining: La Loggetta

As a holidaymaker…

There is a saying in Italian, Passeggiata, which means to stroll in a town looking good. The chicer the town, the chicer the passeggiata. Cortona is definitely the town to do this in. Of all the Tuscan towns we toured, this one felt and looked a little bit different. The winding alleyways and buildings were a bit more elegant. I fell in love with the pale blue-grey stone buildings; as well as, the finer shops and restaurants that you will find here. Cortona, is a definite must experience town when in Tuscany. 

Visit Cortona, a hilltop town in Tuscany. This historic old town has a lot of interesting history in Italy.
Visit Cortona, a hilltop town in Tuscany. This historic old town has a lot of interesting history in Italy.


    • The.Holidaymaker

      Thank you Faith for taking the time to read and comment. Life doesn’t get any better than a gelato in hand and strolling this lovely historic town.

    • The.Holidaymaker

      Thank you Haley for stopping by and commenting. I hope you get to travel there one day soon!

  • Nic

    This is a great guide for visiting, it’s one of those “regions” you say you want to visit but in fact have no actual idea of exactly where to base yourself or to visit so this is really useful. Next time we’re back in Europe we’re hoping to do more of Italy so this will be awesome.

    • The.Holidaymaker

      Thank you for commenting Nic. I know that exact feeling; Tuscany is a large region and you can’t see every town or village, so how do you narrow down that list. We chose the Siena part of the region and we were in close proximity to many wonderful towns. Cortona happened to be one of those. Hope this helps with your travel planning.

  • Patricia Pagenel

    Tuscany is high on our travel plans for Italy, but we have yet to make it happen! The mix of scenic roads, the small villages, the wine and food, and like in Cortona, the village life, and of course, the Etruscan history – from the walls, the museums, the temple, the tombs… You are giving us Tuscan wanderlust!

    • The.Holidaymaker

      Thank you for your comments Patricia. I am pleased to hear that you already have Tuscany on your travel list. You can’t go wrong! There are so many villages and towns that are wonderful to visit, and Cortona happens to be one of them. It doesn’t matter where you go in Italy, you can always find amazing food, wine and views. Happy travels!

  • Cindy

    I’m thinking of going to Tuscany and Umbria in the fall, and now I want to add Cortona to my list of towns to see. I’m with you – – I like nothing better than wandering narrow streets in towns like these, perhaps with the occasional break for gelato or vino.

    • The.Holidaymaker

      How fantastic Cindy that you may be going to this area in the fall. I am happy that I was able to inspire you to add Cortona to your list. Thank you for your comment.

  • Jerry and Fiona

    We missed Cortona twice on our trips to Italy, opting for Pitigliano and some towns in Umbria instead. The Etruscan influence in that part of Italy is really interesting to us. That passeggiata is something else, too.

    Missing Cortona twice means we must return to finally see it one day – which is fine with us!

    • The.Holidaymaker

      There is nothing wrong with returning for a third time! I want to explore more of the Umbria area and that will be our next trip there hopefully. Thank you for your comment.

  • Sage Scott

    Of all your magnificent photos, I’m most drawn to the church dome in the first one. It looks like a smaller-scale version of Brunelleschi’s Dome atop the Santa Maria del Fiore in Florence. Do you see the resemblance? ~ Sage Scott, the Everyday Wanderer

    • The.Holidaymaker

      Thank you for your comment and your kind compliment. Yes, I do see the resemblance after you now say this.

  • Laura Pedlar

    I have loved my visits to Italy but I’ve only been to the major cities so far. This looks like a quieter way of life in Tuscany. I like people watching in piazzas and I also love gelato! I’m not a big fan of visiting churches but I think that this place might be nice to stop on an Italian road trip.

    • The.Holidaymaker

      Thank you for your comments Laura. Tuscany is indeed the laid back and relaxing region of Italy. It’s slow pace of life is definitely intoxicating. We always try and mix large, vibrant cities with a relaxing beach or rural destination all within the same holiday. It feels like a holiday within your holiday. I too am not a big fan of visiting every church or museum either, but at least try and take a picture of the main attractions of each place we visit. Our ideal is just to wander the streets, eat good food, peruse the shops and take in the surroundings. Italy is definitely a great road trip kind of country.

  • Louise France

    Would love to visit this whole region one day and dedicate some time exploring towns like Cortona

    • The.Holidaymaker

      Thank you Louise for your comment. The best part of Tuscany is that many of these wonderful must-see towns are in close proximity making it easy to fill your day with 2 or 3. Hope you get to travel to the Tuscany region one day soon.

  • April Key Rode

    I always enjoy your article about Europe and it’s good to read this one! Italy is in our bucket lists and yes gelato is a must try in visiting this country! Happy travels and thanks for sharing!

    • The.Holidaymaker

      Thank you so much April for being a faithful follower of my blog posts! It is great to hear that Italy is on your list, and hope that this has inspired you to perhaps move it up the list ;).

  • Josy A

    This is all beautiful, but that view from the hilltop of the Val di is just perfect!

    This is one part of Italy that I know embarrassingly little about so your words and wanderlust-inducing photos are incredibly helpful!

    • The.Holidaymaker

      Thank you Josy for commenting and your kind words. I am always happy to share my travels and hopefully inspire future plans, so I do hope that you get to travel to this wonderful part of Italy. Oh, yes, the hilltop views are beautiful.

  • Nitin Singhal

    Beautiful medieval town!! I love how diverse Italy is. It has beaches, ancient ruins, medieval towns, city on canal. Hope I get to visit Italy someday.

    • The.Holidaymaker

      Thank you for your comment Nitin. I absolutely agree – Italy has wonderful diversity in landscape and makes for a fantastic travel destination. I think that is why it is one of the most popular European countries for holiday. I hope you get there one day soon too!

  • Life Of Y

    Cortina looks like such a lovely town! It’s not one I’m familiar with but I’m glad I stumbled across your post! I guess that’s another Italian gem I want to enjoy a gelato in. Especially if Snoopy is serving!

    • The.Holidaymaker

      Thank you for your comment. Yes, indeed it is the perfect town to stroll and have a gelato in! Thanks for stumbling on my post, hope you return again.

  • Heather

    I love that the Estruscan walls are built into the medieval walls. So cool! I would definitely visit Cortona. I need to go back to Italy and see so much (only been to Rome). If I read correctly am I saying this right: Good to know that Cortona has very chic passeggiata! 🙂 Gelato in Italy is so flipping awesome and cute name-Snoopy!

    • The.Holidaymaker

      Thank you for your comments Heather. Yes, you are indeed saying it correctly; and Cortona is one of the more upscale Tuscan towns where you can definitely witness passeggiata! Glad to hear that this has inspired you to potentially add to your future travel itinerary when you return to Italy.

  • Michael Hodgson

    We have always avoided Cortona simply because it was featured in Under the Tuscan Sun … book and movie. But may have to reconsider, though there are sooooo many amazing Italian cities we want to see first … all with amazing gelato and passeggiata tradition … with gelato being of highest priority naturally.

    • The.Holidaymaker

      Thank you Michael for commenting. I agree, I am slightly opposed to any place that is considered a novelty for tourists as well. if you go in the evening or even early morning, you will instantly forget that fact, and enjoy the beauty of this town.

  • Mohana

    Your photographs are captivating!! They grab the attention right up at the front. The guide too is beautifully pieced together and offers a well-balanced experience for a visitor in Cortona. Piazza della Repubblica seems to be THE place to be. Thank you so much for sharing 🙂

    • The.Holidaymaker

      Thank you for your kind comments and compliments. I am very appreciative of you taking the time to read it. You are right, the Piazza is THE place to be while in Cortona.

  • Erica

    Great photos! Italy is so stunning, no matter how much you see, there´s always more places to go back for! I´ve yet to explore the Tuscany region that these pictures definitely inspired me. I love the rolling green hills and cobblestone villages like Cortona, and sounds like the perfect place for a chic passeggiata and a gelato!

    • The.Holidaymaker

      Thank you for your comment Erica. Tuscany is a region of Italy that is so wonderful to explore when you want a laid back and relaxing holiday. We added this in the middle of visiting larger cities and it was a perfect way to unwind and really soak up what Italy is known for and that is good food, wine and scenery. I am always happy to inspire, and glad I did here.

  • Jas

    Tuscany is super high up on my list and reading this just makes me wanna fly over right this second! Piazza della Repubblica is just beautiful and it sounds like the perfect place to spend a relaxing afternoon. The views at the top of Val di are stunning too. I’m in awe!

    • The.Holidaymaker

      Thank you Jas for your comments. If we all could just have the luxury of packing our bags and going wouldn’t that be a wonderful notion. Alas, most of us aren’t able to travel on a whim. That is what makes blogging fun, that you hope it inspires future plans and itineraries.

  • Riana Ang-Canning

    What a beautiful town! I remember being so blown away by the views from San Gimignano, and these ones look just as impressive. You’ve also reminded me that I’ve read Under the Tuscan Sun but I don’t think I’ve ever seen the movie. I must rectify this ASAP!

  • barry

    Iv’e been to many places in Italy but Tuscany has still eluded me. The area looks impressive and those overhanging buildings on Via Janelli are beautiful – just the sight I love to see in an old town.

    I know there are so many places to see in Tuscany but your post makes me want to put Cortona at the top of the list.

  • JoJo Hall

    Little towns and hill top views are always amazing, let alone in Italy, they’re just stunning! It’s my plan to visit smaller towns and places in Italy the next time I’m over there as I know they have so much to offer!

  • Emma

    I love the medieval streets of old towns like this. Cortona looks beautiful and such amazing views! I haven’t been to Tuscany but now I’ve also got a new book for my reading list

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