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.

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.

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.