Two days in Cortona. Wine. Dine. Explore


Make sure you look up when walking around Cortona; there are some beautiful buildings, balconies and frescoes. Sit on the town steps of the Palazzo Comunale with a gelato and watch the world go by or dip into the shops on Via Nazionale and Piazza Della Repubblica which has many shops from tailor-making shoes, hats, or handbags to custom perfume making. This is the heart of Cortona, where the Italians enjoy their ‘passeggiata’ an evening walk before dinner.

Watch the world go by with some Gelato and sit on the steps of the Palazzo Comunale – the city’s 13th-century town hall and clock tower.

If you enjoy shopping, you’ll love Cortona! It’s home to impressive wine merchants and has an abundance of local arts, crafts, and jewellery designers. Located right on the Piazza, Casantonio 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 want to buy one of their larger items.

On your first day in Cortona, we recommend the first thing you do is simply wander around, explore, soak up the atmosphere and live like a local. Cortona is one of the oldest wall towns in Italy and is full of little side streets and cobbled alleyways, gelaterias, cafés, enotecas, shops and restaurants. Enjoy the Italian tradition of starting your day off with a coffee and cornetto in Bar Signorelli.

Pro Tip – Make sure to get your shopping and eating done before around 2 p.m. – most of Cortona closes in the middle of the day so the locals can take a break. Most places re-open later in the afternoon. 

1 PM – 2 PM: LUNCH

Cortona is known throughout Tuscany for its great selection of authentic restaurants. There are plenty to choose from, and most of them are family-run creating dishes from recipes that have been handed down from generation to generation. La Grotta serves simple, delicious food, we love the grilled chicken with spinach and roasted potatoes, Il Cacciatore makes homemade pasta including a mouth-watering carbonara and both of these are less than a minute’s walk from Palazzo Passerini.

Stop at any café or restaurant you pass in Cortona and you’ll enjoy friendly service and great food.

2 PM – 7 PM:

Lunch should be a leisurely affair so 2 pm for sightseeing might be a little ambitious! There are many churches and museums to visit in Cortona. Take a deep breath, put on some walking shoes and climb the hill to visit Santa Margherita Sanctuary located just 1 km from the centre. Along with the Girifalco Fortress, this fantastic church represents the patron saint of Cortona. This church is nestled in the highest area of the town with far reaching views of the surrounding hills and valleys.

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.

Simple, authentic and delicious food can be found in most restaurants in Cortona.

7 PM:

Every restaurant in Cortona will serve you simple, delicious food. There are many beautiful restaurants in the town centre to choose from, some of our favourites include La Loggetta, Osteria del Teatro, Il Cacciatore and La Bucaccia….. This family-owned restaurant 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.

As the leaves turn golden and the air becomes crisp, the local restaurants come alive with the rich aroma of truffles. From creamy pasta dishes to indulgent risottos, these gastronomic gems take centre stage on many of the menus, showcasing the exquisite flavours of the region.

Take a stroll after dinner through the charming streets of Cortona. As the sun sets, the town transforms into a magical haven, illuminated by the soft glow of streetlights. Don’t be surprised to find the little wine bars still buzzing with activity late into the night. Sip on a glass of local wine, savouring the moment before heading back to Palazzo Passerini.


If you want to learn how to make some classic Tuscan dishes why not book a Tuscan Cooking Class. There are so many activities that will help you immerse yourself in the local culture. Tuscan experiences must be made at the time of booking and 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!

In Italy, the day starts with an espresso or cappuccino at the local bar. There are several cafés along Via Nazionale and the two main piazzas where you can stop for a coffee and a ‘cornetto’ (croissant). Relax and watch Cortona come alive, 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!



If you’re after a culinary adventure then book a Tuscan cooking class. Whether you prefer the vibrant energy of being in the town or the charm of the countryside, there are plenty to choose from. Immerse yourself in the art of Tuscan cooking and master how to make the best Italian dishes at home with your newfound knowledge.

Draw inspiration from the local ingredients; during the course, you’ll shop, prepare and dine. Bring the cooking experience back to Palazzo Passerini so you can indulge in cooking and enjoy it privately in your own space. Armed with Tuscan tips and newfound culinary knowledge, you’ll be able to create a feast that will delight the senses!


Truffles are elusive treasures that have captivated the palates of gourmands worldwide for centuries. As you enter the exciting realm of truffle hunting, prepare to be charmed by the presence of an adorable four-legged companion. This skilled canine, trained to detect the intoxicating scent of these rare delicacies, will lead you through the unspoiled beauty of nature, revealing the secrets of the forest with every step.

Witness the dance of sunlight filtering through the lush canopy, casting a gentle glow upon the forest floor. With each passing moment, you’ll feel a deeper connection to the natural world, as if you’ve stepped into a realm untouched by time.

As the hunt ends, prepare to indulge in the sweet aroma of truffles that fills the air. A lovingly handcrafted truffle-themed lunch awaits; every bite is a symphony of flavours, carefully crafted to showcase the unique characteristics of these prized ingredients. 

This is a journey that combines the wonders of nature with the pleasures of gastronomy, a true feast for the senses.


Nestled amidst the verdant hills of Tuscany lies the walled town of Cortona, a true embodiment of the region’s rich winemaking heritage. We invite you to journey through the breathtaking Tuscan countryside, accompanied by your private driver and discover Montalcino, Montepulciano and Chiani.

As you drive along the winding Tuscan roads, a tapestry of olive groves and vineyards unfolds before you, their lush greenery stretching as far as the eye can see. You’ll visit local wineries, where passionate vintners will guide you through the art of wine production and offer you the opportunity to savour their finest creations.

But the experience doesn’t end with wine alone; you’ll have the chance to enjoy authentic Italian food expertly paired with the region’s exquisite wines. From hearty pasta dishes to succulent meats each bite is a celebration of the rich culinary traditions that have flourished in Tuscany over the centuries.

Soak in the sights and sounds that define the essence of Tuscany; magnificent rolling hills, vineyards and olive groves that dot the landscape.

We work with our trusted partner, Molesini Wine Shop, who will help you experience an unforgettable wine tour starting with a tasting in their shop. 


Pay a visit to the very famous Under the Tuscan Sun House, Villa Laura. Located just 3 km from the centre of Cortona, Villa Laura is an incredible villa, designed to capture the romantic essence of Tuscany. 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 Cortona and take in an authentic Italian dinner at La Bucaccia and ask for their steak (prepared rare) and chestnut ravioli. Another great option is Osteria del Teatro, which serves a delicious truffle fondue.



Montepulciano – Pienza – Montalcino – Cortona

  • Pienza is a charming hill town in Tuscany famous for Pecorino cheese (most of the shops can vacuum pack and ship back). The rustic streets are lined with small art galleries and speciality food 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. Walk along Via del Bacio – ‘street of the kiss’ to enjoy the surrounding views. 45 minutes from Cortona
  • Hot Springs of Bagno Vignoni – a once-in-a-lifetime mineral pool experience. 
  • Montepulciano is a small, historical Tuscan town, famous for its vino nobile red wine. Immerse yourself in fine wines and art at Icario, a loftlike, art-filled space where you can taste their signature Sangiovese wines. This medieval hilltop town is also worth visiting for its architecture, history, delicious food and wonderful views.                45 minutes from Cortona
  • Montalcino is close to the Crete Senesi in the Val d’Orcia in the province of Siena. This fairytale hilltop town is famous for the production of Brunello one of the world’s best and most appreciated Italian 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. 1 hour from Cortona
  • 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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