Cortona (Arezzo)

Another of the towns we can see from the house, high up on the side of the Apennines, is Cortona. Cortona is the venue of long long views, a great Gelato and our favourite passeggiata by far.

Nestled in the heart of the region of Tuscany, the charming town of Cortona is a must-visit destination for anyone interested in exploring Italy’s rich history and natural beauty.

Cortona, situated in the Val di Chiana valley and surrounded by rolling hills, woodlands, and vineyards, is an ideal location for outdoor activities and wine tastings. Cortona, with its old alleys, medieval structures, and other cultural attractions, also provides a plethora of opportunities to learn about Tuscan art, food, and traditions.

Things to do in Cortona, Italy

Cortona is a charming town in the heart of Tuscany that offers a rich mix of cultural attractions, natural beauty, and delicious cuisine. Here are some common and lesser-known things to do in Cortona:

  • Explore Cortona’s rich history and cultural heritage: the Etruscan walls, the Church of San Francesco, and the Museo dell’Accademia Etrusca are just a few of the historical landmarks and cultural attractions.
  • The Monastery of Camaldoli is a beautiful and peaceful destination that offers a unique blend of spiritual and natural beauty. It is located in the Camaldoli Woods, a nature reserve near Cortona.
  • Discover the local cuisine: Tuscany is famous for its delicious cuisine, and Cortona has many restaurants and food markets that serve traditional Tuscan dishes. You can also learn more about the local ingredients and techniques by taking a cooking class or going on a food tour.
  • Go wine tasting: Cortona is in the Chianti wine region, and many local wineries offer tastings and tours. This is an excellent way to sample the region’s delicious wines and learn about the region’s wine-making traditions.
  • Take a walk in the beautiful countryside: One of the most breathtaking natural areas surrounding Cortona is the Val di Chiana valley. Beautiful rolling hills, forests, and vineyards, and there are numerous walking and hiking trails that allow you to explore the local landscape.
  • Shop for local artisanal products: There are many artisanal shops and markets in Cortona where you can find a variety of local products such as ceramics, leather goods, and wine.
  • Attend a local festival or event: Cortona hosts a number of local festivals and events that highlight the town’s rich cultural heritage, such as the Cortona Mix Festival and the Festa dei Candelieri. These events are an excellent way to learn about Cortona’s culture and traditions.
  • Visit Lake Trasimeno: Another natural highlight near Cortona is Lake Trasimeno, the largest lake in central Italy. Located just a short drive from the town, Lake Trasimeno is a popular destination for swimming, boating, and fishing. The lake is also home to several small islands, including Isola Maggiore and Isola Polvese, which can be reached by boat from the lakeshore.

Why stay at Siena House outside of Cortona

Siena House is a charming and welcoming boutique hotel located in the heart of Tuscany, just 30 kilometers from the town of Cortona. Our Siena House is an excellent choice for both couples and families, thanks to its large and comfortable rooms and suites, on-site amenities, and convenient location.

The Siena House Hotel also provides a variety of amenities and services suitable for both couples and families. The hotel has a saltwater swimming pool, an outdoor kitchen, and several outdoor areas, including a garden and a terrace, where guests can relax and enjoy the beautiful surroundings.

Because of its secluded location and spacious and comfortable rooms that provide a sense of privacy and seclusion, staying at Siena House feels as private as staying in a villa.

Photos and notes from Cortona

Image showing a tuscan hill town piazza in cortona in winter, a bank facade casa risparmio di firenze in the background people walking and a collectables market in the foreground
Collectables Market in Cortona at Christmas

Passeggiata = a stroll in town looking good. Typically after dinner. It’s quite a serious business, the chicer the town, the chicer the passeggiata.

cortona the long long views
Viewing spot at only half way up…

And Cortona is a very chic spot indeed.  In the province of Arezzo – and with a very different feel to the Sienese towns, the buildings lining Cortona’s elegant streets are more frequently plastered.  Featuring more stone and particularly the lovely grey – blue Pietra Serena in their construction as well as endless peeling paint studies in the art of muted greys and aged pastel tones; inspiring for an artistic eye.  Very photogenic, romantic even on a grey day, a trip to Cortona is recommended to all of our guests – and especially to honeymooners looking for that perfect backdrop for stylish fotoricordi.

Image showing a wedding party being photographed in a tuscan hill town. They are standing on worn grey stone steps, with a convertible classic vw beetle in the foreground and the photographer of the wedding party is on one knee close to the car.
The ‘ice cream steps’ in Piazza di Repubblica. the Gelateria Snoopy is just around the corner.

Yes, you can wear high shoes relatively comfortably here and that’s not true in many of our lovely hill towns But bring flats for the hike to the top for the long long views….

image showing a theatre front with a loggia for a covered market at ground level. the theatre is plastered and painted in yellow ochre with deep green external blinds and stone details there is some activity in the piazza and a few white vehicles are visible
Teatro Signorelli, Cortona.

A firm favourite of the American visitor, promoted not only by the ‘Under the Tuscan Sun’ connection, but also by historic connections to the University of Georgia, Cortona has established a reputation as a stylish hill town. Bristling with chic little artisan outlets – fashion, jewellery, leather, a wonderful hat shop, antiques, art, local ceramics, several very good bars, a lovely enoteca and plenty of top notch white tablecloth dining, and a remarkable ice cream shop.

Image showing a dome viewed from above this is the dome at cortona and the view beyond is the val di chiana countryside.
Cortona overlooks Val di Chiana countryside

In Cortona the experience is all about atmosphere.  Passing an hour or two of on the main street watching the world go by in Cortona is rather lovely.

Image showing a man and a woman drinking iced coffee together in a Tuscan hill town
Iced Illy Coffee at Tuscher

If you’re there earlier in the day or you’re feeling more active there’s much to be discovered by heading ‘up’…up beyond the main streets dipping into the residential areas; right at the top the Fortress and a beautiful church with amazing long views. We love Cortona and come often enough, it’s an easy trip for us. You’d most likely find us sitting chatting on the steps in the Piazza Repubblica local style in the Summer between sundown and dinner. In the Winter instead it would be TUSCHER for a Cappuccino, Prosecco or Martini – depending on the time of day.  We might either head for dinner at LA BUCCACCIA or OSTERIA DEL TEATRO or alfresco if a hot Summer evening at LA LOGGETTA overlooking the main square.  If here for an impromptu lunch or having overstayed a Winter morning Cappuccino and (several) pastries at BAR VANELLI downtown in Camucia, we’d most likely lunch at ENOTECA MOLESINI. If in arriving to the tourist-only populated lunch-time Cortona, a leisurely lunch at Molesini followed by a lazy exploration of the beautiful park with it’s large areas of shade, is recommended

cortona the cat on the windowsill

THE DRIVE: 30 minutes from the house PARK just follow the blue ‘P’ signs on the approach, there’s a large car park below the city walls; it’s fairly obvious when you’re close in.  The Cortonese have kindly put a pair of elevators to glide you effortlessly up to the centre VISIT any time of day although bear in mind that only restaurants will tend to be open between 13.00 and 16.00… when everyone’s home eating pranzo SPECIAL EVENTS the annual TUSCAN SUN FESTIVAL DON’T MISS the SANTA MARGARITA church (just head up, up, up…) and the long views from the FORTEZZA above it (before sunset) the evening PASSEGGIATA, Ice cream at GELATERIA SNOOPY, ITINERARY a few hours in Cortona combines well with wine tasting in parts of Chianti, a city visit to Arezzo or town visit to Lucignano – as well as being a suitable dinner stop ‘en route’ home following a trip into Umbria.  Heading cross country from Cortona to the Mall or the Prada factory outlet is also fairly simple.

Siena House is a boutique hotel in Tuscany with British owners.  We write and photograph Tuscany year round as a resource for our guests publishing our insider guide to Tuscany and our blog, Tuscany Reportage.