Hidden Tuscany: Cortona and Arezzo

A private tour in Tuscany doesn’t always transmit the true spirit and treasures of this region as an authentic Tuscany Experience. Our “Hidden Tuscany: Cortona and Arezzo” tour is designed for those who want to head off the touristic beaten path. We present two destinations that are less raved about than others, but we’re sure that they’ll captivate you.


Cortona dominates the Valdichana in the province of Arezzo, in the southern part of Tuscany. The walls of the city, dating back to the Etruscan and Roman ages, rise out of a hill situated 600 metres above sea level, and the breathtaking view offered here even allows one to spot Lake Trasimeno on a clear day.
Cortona is well-appreciated by tourists, and though it is small, is very accommodating. There are many points of interest to visit, including the Etruscan Museum, the Diocesan Museum, and the unbeatable Sanctuary of Santa Margherita and Girifalco Fortress, both located in the highest part of the city. There’s a bit of an uphill climb, but you’ll arrive in just a few minutes. The Girifalco fortress, currently used for concerts and various types of events, was originally a military structure.
Cortona isn’t just all art and history, it’s also the perfect place for an afternoon of shopping amongst storefronts that offer gastronomic products and handmade goods. It’s the ideal place to find the perfect souvenirs to take home. There are also excellent restaurants where you must try the Chianina beefsteak, famous all over the world. And don’t forget the great wines produced in this area, as Montalcino and Montepulciano are just a few kilometres away, and Cortona’s wine bars offer a selection to discover.
Just beyond the walls you’ll find a monastery built by Saint Francis in 1211 called Il Convento Le Celle, which still hosts a few friars even today. Cortona’s international fame is thanks in part to the 2003 film Under the Tuscan Sun by Audrey Wells, which was filmed mostly in the historic centre of Cortona.


Speaking of unjustly neglected destinations, Arezzo is a prime example of the wonders that are often not included in the classic tours of Tuscany. Located in the centre of four valleys (Valdichiana, Casentino, Valdarno and Val Tiberina) this city - internationally known for its goldsmith trade - was founded by the Etruscans before being conquered by the Ancient Romans.
Arezzo has a very rich artistic heritage, and immediately the church of Saint Francis comes to mind. The church is home to a fresco cycle called Le Storie della Vera Croce, or the stories of the true cross, and was created by Piero della Francesca, one of the greatest painters of the Renaissance. Not far is Piazza Grande which annually hosts the Giostra del Saracino, a jousting tournament in medieval costume that colours the city with its parades.
The Duomo of Arezzo, City Hall, and the Medici Fortress embellish the upper part of the city where you can find various restaurants and antique shops, another distinctive element of the city. In fact, during the first weekend of each month, Arezzo plays host to Italy’s most prestigious market dedicated to the world of antiques and vintage furnishings.
Even Arezzo owes a part of its fame to the world of cinema as many facets of the city are visible in Roberto Benigni’s masterpiece film Life is Beautiful, which won three Academy Awards.

Why choose the tour “Hidden Tuscany: Cortona and Arezzo”?

These two destinations can offer the warmth of an authentic 100% Tuscan experience, as they have less tourists and more locals. You can also request a local guide for Cortona and Arezzo so that you can immerse yourself even more deeply into the local life of the cities.

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