Located near the center of Italy is the charming small town of Cortona. As travelers approach the town from the lower areas of the countryside, Cortona appears to be perched just above and watching over all of Tuscany. This under-the-radar town is not typically mobbed by crowds like other parts of Italy and is a delight to visit. Cortona is truly a beautiful way to begin or end an Italian getaway.

This ancient city has been around for centuries and has more recently enjoyed an influx of visitors. Although travelers from all over the world have visited Cortona for more than two hundred years, the introduction of the 2003 movie, Under the Tuscan Sun, brought a new wave of visitors from the United States and abroad. Once you are exposed to the beauty of this amazing town, whether it be via film or in person, Cortona has a way of simply capturing your heart.

Cortona is a quintessential small Italian town. The mostly sloping stone streets boast delicious restaurants, quaint cafés, and unique shops that feature locally made food and goods. The buildings rising up on either side of a street often feature fresh flowers outside windows during the warmer months. To walk the city during the day or during an evening passeggiata is one of the best ways to take in the local culture and customs.

Estimated to have been present since Roman rule or earlier, the town’s large stone walls still stand today. This feature combined with Cortona’s elevated position above much of Umbria and Tuscany, allowed for great military advantages.

Cortona is thought to have once been an Umbrian city that was eventually taken over by the Etruscans. Over the ensuing years, the city fell under Roman rule before becoming allied with the Ghibelline faction circa the thirteenth century. Cortona then became part of the lands of the Medici during the fifteenth century before eventually earning a role in the Unified Kingdom of Italy.

Unlike many of the larger Italian cities, Cortona is not located at the intersection of or alongside major area highways. Sitting atop a hill above the Tuscan countryside, if traveling by car or bus, visitors would be required to exit off a nearby highway and wind their way through Tuscany to Cortona. Be advised that if traveling by car, the amount of parking options within Cortona’s city walls is limited.

For those flying in, the airports of Peretola International in Florence, Sant’Egidio International in Perugia, Galileo Galilei International in Pisa, and Fiumicino International in Rome will likely be your best bets.

When it comes to navigating the city itself, public bus transportation may be preferable to that of your own car so that parking will not be an issue. Many of the locals choose to traverse the city primarily on foot or by bicycle. The charm of this town lies in each city block and is best experienced when exploring at a slower pace.

Even though it is a small town, touring breaks will be needed for meals. With the local cured meats and cheeses, the homemade pasta, and the deliciously creamy desserts, you will want to partake in the Italian tradition of lingering over meals. The dining experience in Cortona and Italy is much slower paced than what travelers of other nationalities may be used to and may take up to two hours or more. Most meals here will consist of an appetizer, first course, second course, and dessert, but no meal is complete without wine. With the city’s close proximity to several renowned wine areas, it is an absolute must to sip on a fine locally-made wine during the course of your meal.

Whether you plan to stay in Cortona for one day or several, the rich history, culture, and cuisine all come together to make this town largely off the beaten path a wonderful Italian vacation destination of a lifetime.


The city of Cortona is located close to the heart of Italy. It is part of the province of Arezzo and the larger, famous region of Tuscany. Cortona is considered to be a part of the Val di Chiana, known as the Chiana Valley, an alluvial valley that is one of the most extensive in the Apennine Mountain range.

Cortona is not a well-traveled vacation destination located alongside one of the country’s major highways. The right highway exit will take motorists through the Tuscan countryside and eventually lead them to this beautiful and secluded town.

Driving in from the Tuscan countryside, Cortona is highly visible as it sits high atop a hill. The city’s elevated position affords visitors some truly breathtaking and picturesque views of the Tuscany countryside and the rolling hills of neighboring Umbria. Weather permitting, travelers may even catch a glimpse of the nearby Lake Trasimeno, which is the fourth largest lake in the country and the largest in Central Italy. However, other than those bodies of water that can be seen from the edge of Cortona looking out over Tuscany and Umbria, the town is largely landlocked.


Cortona is most commonly visited during the summer months as that tends to be when the town is warmest. The warm summer weather hits in earnest around the middle of June and ends in early September. On average, tourists can usually expect temperatures around 80 degrees Fahrenheit with lows in the 60s. The summer months are statistically lower in rainfall than the remainder of the year.

The coolest part of the year begins in late fall and typically stretches until early spring. During these colder months, the city generally experiences temperatures around the 50s during the day and can bottom out in the 30s overnight.

Despite the temperature, the city of Cortona is just as beautiful when it is warm as it is when the cold sets in. For this reason, there is really not a bad time of year to visit the town.


Because Cortona sits perched above Tuscany and the foothills along the edge of Umbria, the city offers unparalleled panoramic views. By standing upon a wide terrace on the clearest of days, viewers can see the two regions in one sweeping glance. One of the best ways to enjoy such a view is with a glass of locally-made wine or a sweet gelato in the company of good friends.

Another particularity of the city is the presence of one main street that is conspicuously flat. The hilltop location makes the sometimes steep sloping streets of the city a part of everyday life, except for a street called Via Nazionale. Despite its official name, many of the residents refer to the street by its nickname, Rugapiana, which translates to flat wrinkle. Because it is the only truly flat road in Cortona, it is one of the main thoroughfares often traveled by townspeople and visitors.

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