Cortona, is a beautiful Tuscan town. For most of us, we were first introduced to this hilltop town first through the book by Francis Mayes, and then the movie. Under the Tuscan Sun put Cortona Italy on the map. 

This Tuscan town lies in the province of Arezzo, in the Chiana Valley in southern Tuscany. Cortona to Florence is a 90-minute drive. Check out our Guide about Florence here. 

Perched on top of a hill, Cortona is an ancient walled town with lively piazzas, endless winding alleyways and many churches. This is your guide to the best things to do in Cortona Italy.  

Top Things to Do in Cortona

PIAZZA DELLA REPUBBLICA

Perched on top of a hill, Cortona is an ancient walled town with lively piazzas, endless winding alleyways and many churches. Cortona lies in the Chiana valley of southern Tuscany in Italy

The main square in Cortona is Piazza della Repubblica. The buildings that sit along the perimeter date back to the 13th century. Here you will see significant attractions that include a well-preserved town hall, clock tower and former palace. 

Perched on top of a hill, Cortona is an ancient walled town with lively piazzas, endless winding alleyways and many churches. Cortona lies in the Chiana valley of southern Tuscany in Italy

This is a lively piazza, the very heart of this beautiful Tuscan 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. 

THE STREETS OF CORTONA

Perched on top of a hill, Cortona is an ancient walled town with lively piazzas, endless winding alleyways and many churches. Cortona lies in the Chiana valley of southern Tuscany in Italy

The streets in Cortona are steep. You will be going up and down as you make your way through the town. All but one, the main Via Nazionale, which links Piazza Garibaldi and Piazza della Repubblica together. You might hear locals refer to it as Ruga Piana or flat street. Seek out the ancient streets of Via Guelfa and Via Ghibellina. 

Pin on Under the Tuscan Sun

Another top attraction is to 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

Perched on top of a hill, Cortona is an ancient walled town with lively piazzas, endless winding alleyways and many churches. Cortona lies in the Chiana valley of southern Tuscany in Italy

Cortona is believed to have been a powerful Etruscan town during the 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.

Perched on top of a hill, Cortona is an ancient walled town with lively piazzas, endless winding alleyways and many churches. Cortona lies in the Chiana valley of southern Tuscany 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.

CHURCHES IN CORTONA

Perched on top of a hill, Cortona is an ancient walled town with lively piazzas, endless winding alleyways and many churches. Cortona lies in the Chiana valley of southern Tuscany in Italy

Even in a small town, there are a lot of churches in Cortona. All playing a significant role in history makes each of them interesting to visit. My favourite, pictured above, can be found on the outskirts of Cortona. The Santa Maria delle Grazie al Calcinaio, also called the Madonna del Calcinaio was built in 1513 and is one of the most architecturally important Renaissance churches in all of Tuscany. Here are others to visit:

  • San Francesco is considered one of the earliest Franciscan churches (1245)
  • Cathedral of Santa Maria Assunta, a Renaissance structure (15th century)
  • Church of San Doménico (15th century)
  • Sanctuary of Santa Margherita, a pilgrimage church (19th century)

MUSEUMS IN CORTONA

The best way to learn about the interesting history of Cortona is to visit its museums. Here are the top ones to visit:

  1. The small Museo Diocesano, or Diocesan Museum across the piazza features a superb art collection. It depicts the town’s history from the 3rd century to the 18th century. 
  2. Wander the fascinating Museo Etruscan Museum displaying artifacts from the Etruscan and Roman eras. 
  3. 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.                             

GIRIFALCO FORTRESS

Perched on top of a hill, Cortona is an ancient walled town with lively piazzas, endless winding alleyways and many churches. Cortona lies in the Chiana valley of southern Tuscany in Italy

The Girifalco Fortress overlooking Cortona dates back to 5th or 6th century. The fortress walls connect to the town walls and create a pentagonal-shaped, internal courtyard. It is one of the favourite viewpoints for admiring the surrounding Tuscan landscape.

VIEWS FROM CORTONA

Due to being perched on a hill, Cortona’s views are incredible.  There are a few piazzas and alleyways where you can gaze upon the view of the Val di Chiana and Lake Trasimeno. 

Best Places to Stay in Cortona

Cortona can easily be seen in one day, but if you would like to make Cortona your home base, this ancient town offers a wide range of accommodations, both in town and close to it. Here are some of the best accommodations in Cortona.

  • Hotel in the old town: Hotel San Michele is located inside one of the oldest buildings of Cortona, the ancient Baldelli Palace. Updated rooms in the 15th century palace overlook the terra cotta roof tiles and the countryside views beyond.  
  • Luxury countryside villa: Relais La Corte dei Papi offers luxurious accommodation in a tranquil, romantic setting just 10 minutes from Cortona. This 18th century villa with a pool also offers fine dining restaurant
  • Agriturismo in a great locationAgriturismo Pagliai is a 15th century estate that produces its own olive oil and vegetables. Stay in a rustic suite or individual apartments.
  • Apartment in the historic town centre: Cortona Suite is a on the second floor of a 15th-century building overlooking Piazza Signorelli square. A light breakfast is available for your stay.  
  • Or, explore other properties using Booking.com

Here are some best places to eat in Cortona:

  • Gelato: Gelateria Snoopy 
  • Wine bar: Enoteca Molesini 
  • Coffee:  Café Tuscher
  • Alfresco dining: La Loggetta

Best Day Trips from Cortona

The beautiful Tuscan views from Cortona, Italy

If you’ve decided to make Cortona your home base, here are some popular day trips you might wish to take. 

  • Villa Bramasole – tourists flock to the villa that was featured in Under the Tuscan Sun. And there are two, one where the movie was filmed and the other is the real villa Francis Mayes bought. Both are within walking distance from Cortona
  • Pienza – a 15th century Renaissance town designated a UNESCO World Heritage Site is a 50-minute drive. Check out our Guide of Pienza here. 
  • Montalcino, Montepulciano, and Arezzo – are all notable hilltop towns in under an hour’s drive from Cortona. Check out our Guide of these Tuscan towns here.
  • Siena – a medieval city that is known for its 13th century Piazza del Campo, considered to be one of Europe’s greatest medieval squares. Siena to Cortona is an hour’s drive. Check out our Guide to Siena here. 

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. 

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47 Comments

  1. 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

  2. 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!

  3. 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.

  4. 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!

  5. 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!

    1. 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.

  6. 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!

    1. 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.

  7. 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 🙂

    1. 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.

  8. 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.

    1. 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.

  9. 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!

    1. 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.

  10. 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!

    1. 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.

    1. 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!

  11. 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!

    1. 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.

  12. 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!

    1. 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 ;).

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

    1. 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.

  14. 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.

    1. 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.

  15. 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

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

  16. 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!

    1. 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.

  17. 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.

    1. 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.

  18. 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!

    1. 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!

  19. 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.

    1. 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.

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

    1. 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.

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