Best of Tuscany: Cortana, Italy
View below Cortona’s walls overlooking Val di Chiana.
You can try to persuade me there’s a better town in Tuscany than Cortona, Italy.
Tuscany is absolutely gorgeous and this region full of destinations one should not miss! Unfortunately, it takes much longer than a lengthy holiday to truly soak in the glory of Northern and Southern Tuscany.
However, if you’re searching for the complete Tuscan experience in just one destination, Cortona is the picture-perfect town to embrace la dolce vita (the sweet life). Plan your stay in this Italian oasis and Cortona will be your favorite, too!
Arriving to this hilltop town makes a lovely first impression. Situated almost two-thousand feet above sea level, Cortona instantly wows all with its sweeping views of Val di Chiana below. Quickly, eagerness to discover life behind Cortona’s strapping fortress-like walls sets in.
Charming in every way imaginable - Cortona is an beautiful medieval town, featuring Renaissance period architecture and timeworn cobblestone streets. An expert tip – be sure to pack walking shoes. Visitor vehicles are not permitted within the town walls, so you’ll have to take a short walk up a slopping street to reach Cortona’s epicenter – Piazza della Repubblica.
The epitome of the word “community” – Piazza della Repubblica is a jubilant display of the Cortonese lifestyle. Best described as the heart of Cortona, Piazza della Repubblica is the best place to enjoy pastimes such as people watching. From here you’ll see people spread out on the Palazzo Communale steps enjoying the day and Cortona’s older generations congregating around the piazza benches, perhaps to chat about the latest town gossip.
Aperitivo at Bar Caffe Signorelli.
In the early evening, Piazza della Repubblica comes alive for aperitivo. A lovely Italian tradition, aperitivo is best described as the time after work and before dinner, in which people meet with friends to relax over cocktails and hors d’oeuvres. Compared to an American “happy hour”, aperitivo is takes place later in the evening since Italians generally eat dinner around 9:00 PM. In Cortona, our favorite place for aperitivo is al fresco in Piazza della Repubblica at Bar Caffe Signorelli.
Cheese wheels in Cortona, Italy market.
Another true Italian experience, shop Cortona’s Saturday Market. On market days, the town comes together to buy and sell local wares, produce, meats and other Tuscan goods throughout the main piazzas. You’ll want to wake early for this, there is nothing more authentic than buying juicy, ripe tomatoes, fruit and a cheese wheel directly from Cortona’s local farmers. Absolutely delicious.
Views from Piazza Garibaldi in Cortona, Italy.
Steeped in deep history, Cortona’s beautiful views are all paired with stories to be uncovered. Once conquered by the Etruscans long ago, pieces of their reign are still visible today – just check out portions of Cortona’s ancient walls! The best view of the area is located at the historical landmark, Piazza Garibaldi. From this point, you can see Lake Trasimeno – where Hannibal led the largest ambush in history against the Romans – and the best panoramic views of Tuscany.
Views from Duomo Santa Maria Assunta in Cortona, Italy.
Another view one must see, sneak away for the golden hour before sunset at Duomo Santa Maria Assunta. One of the best places for this special lighting, here you’ll witness the sun’s gold castings lay onto the surrounding olive groves below. After the sun goes down, the blue tones over the hills creates an incredible sight.
Basilica of Santa Margherita in Cortona, Italy.
Cortona is a fantastic destination for active visitors. Venture beyond the town walls and embark on a hillside exploration through Tuscany. An intoxicating adventure, hiking through Tuscany’s olive groves and ancient roadways is an experience you’ll never forget.
Hike to Cortona’s most-loved sights, such as Basilica of Santa Margherita. From here, you’ll see more panoramic views of Val di Chiana and Lake Trasimeno. For a more mysterious adventure, visit Tanella di Pitagora. Located just beyond the town walls, this Hellenistic tomb is said to be from third or second century B.C. It’s unclear the tomb’s exact story, however, ask around Cortona and you’ll hear many different mystifying stories of the tomb’s ancient history.
Ristorante Tonino overlooking Val di Chiana in Cortona, Italy.
Dining in Tuscany is one of the main attractions and despite Cortona’s small size, you’ll be pleasantly surprised by its lengthy list of restaurants. From pranzo (lunch) to cena (dinner), you’ll get the full Tuscan dining experience! For the ultimate dining view in Cortona, Ristorante Tonino offers outdoor dining overlooking Val di Chiana.
Insalata Caprese in Tuscany (Fresh mozzarella di bufala, roma tomatoes, basil & oregano).
Maximize your vacation time in one of the best destinations in Tuscany – Cortona, Italy. Although, it’s not a best-kept secret, Cortona is a great town to get away from the hustle and bustle for an authentic getaway “Under the Tuscan Sun”.
A town often overlooked by travel guides - for larger destinations such as Siena, San Gimignano and Florence – Cortona is a wonderful jewel of Tuscany. If your graced with a generous amount of time to travel Tuscany…visit Cortona – and beyond. Northern and Southern Tuscany are significantly different and deserve to be on your bucket list. Other cities and towns I recommend for your Tuscany itinerary – Florence, Lucca and San Gimignano.