

« We travel not to escape life but
for life not to escape us »Robyn Yong
Cortona is truly a Tuscan treasure. This hilltop medieval town dates back to the Etruscan period over 2,500 years ago and sits majestically in the south-east region of Tuscany. Its old world architecture, culture and charm melds with the hustle and bustle of modern Tuscan life making it vibrant, alive and timeless!
“A dream came true for us the summer of 2016 when we got to live “Under the Tuscan Sun” in a charming villa just a few minutes walk into the town of Cortona. We had to pinch ourselves. This was Frances Mayes’ country and we were living it! We were so captivated by the experience that we returned in September 2017. This time our intent was to capture and document our experience to share with you. It was love at first sight as we drove through Villa Cristina’s gates.”

Renovated in 2015, Villa Cristina features its original 5 metre high brick vaulted ceilings on the main floor. Seventeen Century wood beams and antique glazed “cotto” tiled floors, are mixed with modern touches all blending as if original. The main floor contains a spacious kitchen and a great room with an antique refectory table that seats 10-12 comfortably. The kitchen contains all the conveniences of modern living including a dishwasher. However, in true Tuscan style, a wood burning oven was built in the corner giving an old world feeling to the heart of the home. Two sets of french doors open to the terrace with its stone table sitting under a vine laden portico—marking the spot where we gathered to start and end each day under the stars.




















« Church bells ring out from the church below beckoning a new adventure under the Tuscan sun. »



The town of Cortona is a stroller’s paradise. As you explore the winding narrow streets thatcircle the hill, you realize that it is a living, working town with a bustling daily life. Visiting as atourist for the first time, you stand captivated watching its inhabitants come and go throughout this walled city busy with their daily rituals. It is a town full of narrow shop-laden streets, medieval treasures, hidden stone staircases. All ready for discovery.

The main entrance into the town is via Nazionale which leads into the centre of town and the Piazza della Repubblica. The town hall with its impressive clock tower and prominent staircase dominate the square. Here you will see some familiar sites from the movie, “Under the Tuscan Sun” documented with wall plaques.
Imagine dinner at La Leggetta under the vaulted ceiling of its terrace on a warm summer’s night watching the sun set behind the clock tower sipping wine and dining on one of Chef Marco’s traditional Tuscan dishes as the stars come out. The town of Cortona is the perfect setting for you to create your own magical moments.



You will never go hungry or thirsty in Cortona. The streets are filled with artisanal shops carrying an abundance of Tuscan products and fresh produce that literally spill out of the doorways. Our two favourites are run by the Molesini family both located in Piazza della Repubblica. They opened in 1937 and are still going strong 3 generations later. The “supermarket” offers a wide selection of fresh produce, package products and household needs. The Enoteca Molesini across the square prides itself as purveyors of fine regional wine and offers wine tasting to small groups.

Saturday is market day in Cortona. Local farmers set up their stalls in the Piazza Signorelli from 8:00am to 2pm.


We were lucky to partake in the 2 day “Choc Cortona” chocolate festival held mid September. The finest craftsmen from across Italy showcase their handmade chocolate. The air is filled with its delicious scent enticing you to indulge.



The most important festival in Cortona is the “Sagra della Bistecca”(Steak festival) celebrating the famous Chianina cattle which is considered one of the oldest breeds in the world. Considered to be the most important gastronomic festival of the year, it takes place in the public gardens of Parterre and is held in mid August. T-bone steaks are cooked according to an old Tuscan tradition and served with local wines.



Artisanal Italy is alive and abundant in Cortona. It is a shopper’s mecca with its beautiful boutiques filled with hand-crafted pottery, jewellery, clothing and shoes.

Wandering through the streets of Cortona a discovery is made around each bend in the road. Make sure to visit the Medieval houses of the 1300s on Via Iannelli. These Cortonese homes with their original overhanging beams date back to the Estrucean era.





Although Cortona is a city of stone, bursts of bright flowers and greenery adorn the streets and greet the passerby at every turn.





"In the heart of the historic center of Cortona, located in Piazza della Repubblica in front of the majestic Palazzo del Comune, stands the Antica Gioielleria in Cortona.” The shop is filled with original jewellery pieces, handmade by local Italian artists.




Cortona is Frances Mayes’ country made famous by her book, Under the Tuscan Sun. A trip to this hilltop town would not be complete without a leisurely walk to her beloved Bramasole so exquisitely renovated and nestled along the roadside just 2 km outside of town. To get there… find the entrance of the park at Piazza Garabaldi located at the end of Via Nazionale. Walk through the park to the end where the tennis courts are located. Follow the road, staying to the left when it forks. Take notice of the 100 year old cypress trees lining the road high above the valley on your right. You will see the Mayes’ beautiful peach home sitting proudly on the hill among the gardens.

What to See:
- Piazza della Repubblica - “The heart of Cortona.” All roads seem to enter into the main square. The town hall dominates the square with its prominent staircase dating from the 13th century to incorporate the distinctive clock tower.
- Via Jannelli - picturesque street with some of the oldest medieval houses in Italy with original wooden support beams
- Basilica Santa Margherita - neo-gothic 19th century church with 13th century wooden crucifix
- Museo Diocesano - opposite cathedral has artifact and paintings from 12th-17 centuries
Museo dell’Accademia Etrusca - Etruscan artifacts including a bronze chandelier from the 4th century BC. - Chiesa di San Francesco - dating back to 1245, one of the earliest Franciscan churches
- Chiesa di Santa Maria Assunta - Renaissance structure built over a Romanesque church
- Chiesa di San Niccolo - small church at the top of town
- Duomo 16th century building incorporated into an earlier Romanesque building
- Bramasole - Frances Mayes’ beautiful villa - a beautiful walk along a long winding road on the outskirts of town.
Where to Eat:
Restaurants in Cortona specialize in menus that reflect the flavours and tastes unique to the season.
- La Loggetta - via Piazza Pescheri ~ housed in a 12th century palace with an outdoor terrace that gives a spectacular views of town hall with its impressive bell tower (famous for its scene in Under The Tuscan Sun)
- Osteria del Teatro - via Maffei ~ an elegant restaurant located in a 6th century building known for its cheese fondue with black truffle shavings
- Cortona Bistrot - via Santa Margherita ~ a tiny intimate 8 table restaurant run by a husband and wife. Additional seating is available outside and across the street by the wall
- Trattoria Toscana via Dardano ~ just a few steps from the main square small, cozy restaurant run by the Cenci family featuring typical Tuscan cuisine
- Taverna Pane e Vino - via Piazza Lucca Signorelli ~ located in old cellars dating back to the 14th century - a favorite of Frances and Ed Mayes
- Bar Tusche - via Nazionale ~ located on the main street into town great place for coffee, glass of wine, lunch or dinner
- Gelato Ti Amo - via Benedetti ~ favorite gelato spot
Favorite Spots - coffee & pastries
- Pasticceria Banchelli, via Nazionale - Always a buzz of activity, it became our favourite “go to” place for morning coffee and pastries located on the road leading into the centre of town.
- Cortona - Caffè Vittoria - Sit among the locals and watch Piazza Luca Signorelli come alive.
- Camucia - Paticceria Vannelli - Experience a cappuccino made by one of Italy’s top baristas. Make sure to try EVERTHING! Read about our morning at the Vannelli family’s pasticceria in our Found and Loved
