Two days in Cortona. Wine. Dine. Explore


Once you have gotten a good walk around town, spend some time people-watching or shopping at Piazza Della Repubblica. This is the city centre of Cortona, so there are tons of people to see and places to sit. The Piazza has many shops from tailor-making shoes, hats, or handbags to custom perfume making… and of course, restaurants to explore and enjoy!
Make sure to grab some Gelato and sit on the steps of the Palazzo Comunale – the city’s 13th- century town hall and clock tower. Also, take a wander over to Piazza Signorelli located right next to the city centre.
Cortona’s shopping is exquisite, boasting impressive wineries, a well-preserved Etruscan history, and an abundance of local arts, crafts, and jewellery. The refined shopping at Casantonio creates a luxury local retail experience with top-of-the-line Italian pottery. Located right on the Piazza, this little gem carries every variety imaginable of hand-painted Tuscan pottery. The owner is very friendly and welcoming! They even ship to the U.S. if you wanted to purchase one of their larger items.
On your first day in Cortona, we recommend the first thing you do is simply wander. There is plenty to do in and around Cortona, but first, you must discover what this place is all about. The city is lovely, full of little side streets and stony roadways. The vibe is friendly and traditional. There is an array of local restaurants, little shops, local bars, and gelato places to check out.
Pro Tip – Make sure to get your shopping and eating done before around 2 p.m. because most of Cortona shuts down in the middle of the day so the locals can take a break. Most places reopen later in the early evening. If you can support the local shops this is the place from fresh pasta to Pecorino cheese (not Parmesano)…

1 PM – 2 PM: LUNCH

Cortona is known throughout Italy for its dynamic food culture and that shows in the plethora of delicious restaurants. For a pure Italian experience indulge yourself in local venues for lunch. Select from the many dining establishments throughout the city and feel the Italian sun on your skin. Grab some pizza here, and a pastry there. It is a great way to get a feel for the city or take a seat in any cafe in the city.
If you feel like giving your feet a rest, sit down and try a meal in any restaurant in the city. Located in Piazza Signorelli, their dining terrace sits above the street level giving dinners a great view of the Piazza.

2 PM – 7 PM:

Now time for some sightseeing. There are many churches and museums to visit in Cortona. However, the best experience can be found exploring the Santa Margherita Sanctuary. Located just 1 km from the city centre, along with the Girifalco Fortress, this amazing church represents the patron saint of the city. Conquer the hill and discover the sanctuary. This church is nestled in the highest area in Cortona. The views of the city and surrounding countryside are simply stunning.

Girifalco Fortress is
also called the
Medici Fortress

The Medici Fortress is a beautiful fortification in Tuscany that offers you a privileged glimpse into the history and contemporary life of the countryside. It was restored in 1561 and is one of Italy’s most renowned landmarks. The Fortress has a commanding position over the surrounding countryside and is perfectly placed to remind you just how wonderful Italy can be. Follow the path along the city’s Etruscan walls on your climb up so that you can enjoy breathtaking views of the valley and surrounding countryside. You can even see Lake Trasimeno in the distance.
You can’t go wrong with Italian food and almost every place will serve you something amazing.


And now it’s time for dinner. You can’t go wrong with Italian food and almost every place will serve you something amazing. There are many wonderful restaurants in the town center to choose from, some personal favorites being La Loggetta, Osteria del Teatro, and La Bucaccia….. This lovely place has a nice inside area, but the best seat in the house is on their terrace, which overlooks the main Piazza. Everything they make is homemade with locally sourced ingredients and the place is family-owned.
You will find truffles in many of the dishes they offer but you really can’t go wrong with any item on their menu.

After dinner, take your time getting back to your Palazzo Passerini. The streets at night are magical! And many of the little wine bars stay open late.


Next, book yourself a Tuscan experience! For example, a Tuscan Cooking Class. There are so many activities that will help you immerse yourself in the local culture. Most of these tours can be booked through local tour companies. Please note – all of these must be booked in advance.
Swing by one of the coffee shops along Via Nazionale and the two main piazzas for a coffee and a pastry. Relax and watch the city wake up, it’s a great way to start the day.
Other unique experiences include a falconry experience, driving a Ferrari, bike tour, horseback riding, art tour, olive oil tasting, off-roading tour, and many more. There is something fun for everyone to do!



There are numerous cooking classes in the area, both in town and in the countryside. Participants enjoy learning how to cook authentic dishes from local artisans. You’re in charge of dinner tonight, but it doesn’t have to be stressful.
We recommend that you bring the cooking to your palazzo so you can indulge in both cooking it and enjoying it privately in your space. This cooking class includes shopping, preparing, and dining.


Truffles are one of the most prized foods in the world. You get to follow around the adorable dog that is trained to sniff out these rare delicacies. What’s better than being surrounded by unspoiled nature? This tour will allow you to see the beauty of the forest first-hand. Then indulge in the sweet aroma of truffles and enjoy a culinary experience at a lovingly handcrafted truffle-themed lunch after the hunt


The hills of Tuscany are lush with vineyards producing Tuscan wines, and Cortona is the epitome of this region. We offer a private driver to escort you through the countryside so that you can enjoy fine wine paired with authentic Italian cuisine in one of the many local wineries. Drive into the magnificent rolling hills, vineyards, and olive groves. We work with our trusted partners, Molesini Wine Shop, that help you experience an unforgettable wine tour. First, arrange a tasting in their shop. Then you plan the areas to visit the neighbouring wineries of Montepulciano or Montalcino.


Pay a visit to the very famous Under the Tuscan Sun House, Villa Laura. Located just 3 km from the city centre of Cortona, Villa Laura is an incredible villa, designed to capture the romantic essence of Tuscany and is available to rent. Villa Laura is not open to the public, but curious tourists can catch a glimpse of it on the road.


Your day of wine and shopping is coming to an end. Return to the city and take in an authentic Italian dinner at La Bucaccia. For true Tuscan flavour, ask for their specialties-steak (prepared rare) and chestnut ravioli. Another great option is Osteria del Teatro, with delightful truffle fondue.


  • Pienza is a charming hill town in central Italy. The rustic streets are lined with small art galleries and speciality shops. Pop by the open-kitchen restaurant in La Bandita Townhouse and try the spectacular white-bean soup at Sette di Vino in a tiny piazza.
  • Hot Springs of Bagno Vignoni – a once-in-a-lifetime mineral pools experience. Steep while overlooking a lush valley.
  • Montepulciano is a small, historical city in Italy, famous for its exquisite wines. Immerse yourself in fine wines and art at Icario, a loftlike, art-filled space, where you can taste their signature Sangiovese wines.
  • Drogheria Franci is a place in the heart of Montalcino where people celebrate food. They do an amazing risotto with pumpkin or local white truffles. Locanda Demetra is a place with a farm-to-table concept. All the produce is grown on the property and used in the restaurant.
  • Any number of local trattorias serve Tuscan classics like bistecca fiorentina and pici with wild boar sauce, but you’ll be well-fed at the nostalgically rustic Osteria del Teatro in Cortona.
  • Try Locanda al Pozzo Antico, off the plaza, for tasty home-style cooking.
  • Take a day to explore beyond the 30km range and you will end up in Umbria where you can experience such marvels as the Lago Maggiore. Take your time and take a day to soak up the views of the lake.

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52044 Cortona, Province of Arezzo, Italy

+39 338 2999246