Disclosing Cortona: 15 Unforgettable Things to Do in Cortona, Italy
If you’re planning a road trip through Tuscany, you’re probably already dreaming of rolling hills, vineyards, and medieval villages. But let me tell you — Cortona, this beautiful hilltop town in eastern Tuscany, is a must-see destination that will steal your heart instantly.
Cortona has winding streets that seem to have a story at every corner, panoramic views that look straight out of a postcard, and an atmosphere that invites you to slow down and savor every moment. Cortona is one of those places where time seems to stand still, and before you know it, you’ll be planning your next visit.
I wanted to visit Cortona ever since I watched André Rieu’s Romantic Paradise concert from Cortona. Recently I finally got a chance to explore Cortona on a Tuscany road trip, and I can tell you — it’s not just the scenery that makes this town magical. It’s the sense of history, the warm hospitality, and the sheer beauty that surrounds you at every turn. So, if you’re ready to be inspired, let me take you on a journey through Cortona’s highlights — the things you simply can’t miss when you visit this charming town. Here is my guide to the top things to do in Cortona Italy.
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15 Special Things to Do in Cortona Italy
1. Start with the Views at Piazza Garibaldi
The first stop on your Cortona adventure should be Piazza Garibaldi. It’s not just any square — it’s a viewpoint that offers sweeping, panoramic views of the Tuscan countryside. From here, you can see the vineyards, olive groves, and villages below, all bathed in that golden Tuscan light that makes everything look like a painting. It’s a perfect place to pause, take a deep breath, and let the beauty of the place wash over you.
I still remember standing there, the whole valley unfolding before me, thinking, “I’m really here, in one of the most beautiful places in the world.”
2. Stroll the Cobblestone Via Nazionale
Now that you’re ready to explore, take a leisurely stroll down Via Nazionale, Cortona’s main street. This charming pedestrian avenue is lined with boutiques, art galleries, and cozy cafes. There’s something so wonderful about walking down a street like this — it feels like stepping back in time while still enjoying modern comforts.
I recommend popping into one of the little cafes for a coffee or gelato and simply soaking up the atmosphere. You might find yourself lingering longer than you expected, watching locals chat, tourists snap photos, and the world go by at a slower pace.
3. Discover the Heart of Cortona: Piazza della Repubblica
As you continue along the Via Nazionale you’ll eventually come to Piazza della Repubblica. This is Cortona’s main square and a real highlight of the town. Surrounded by medieval buildings, it’s the kind of place where you’ll want to stop, sit, and take it all in. There’s always something happening here, whether it’s a local market, a festival, or simply people enjoying an afternoon drink. The Palazzo Comunale (Town Hall) adds to the square’s historic charm, standing proudly with its old-world architecture.
Take a seat at one of the outdoor cafes and enjoy a glass of Aperol or wine— the square is perfect for people-watching, and there’s a cozy, inviting vibe that makes you feel like you’ve stumbled upon the true heart of Cortona.
4. Museums and Ancient Artifacts: Museo Etrusco and Tabula Cortonensis
Cortona isn’t just about stunning views and charming streets — it’s also home to a rich cultural heritage. If you’re an art lover or history buff, don’t miss the Museo Etrusco (Etruscan Museum), where you can delve into the town’s ancient Etruscan past. Cortona was once an important Etruscan city, and this museum showcases artifacts from that era, including the famous Tabula Cortonensis, an important bronze inscription that offers a glimpse into the life of the Etruscans.
The museum offers a fascinating journey through time, and it’s one of those places that adds depth to your understanding of Cortona. I always find it amazing to think about the layers of history beneath my feet as I walk through this town.
The entrance fee is 10€. Check out the official website for the opening hours and more info.
5. Cortona Duomo and Piazza del Duomo: A Step Back in Time
No visit to Cortona would be complete without a stop at the Cortona Duomo (Cathedral of Santa Maria Assunta). The cathedral, located in Piazza del Duomo, is a striking piece of Renaissance architecture. Inside, you’ll find peaceful quiet, and beautiful religious art. It’s the kind of place where you can take a few moments to reflect and appreciate the calm and simplicity that pervades the town.
It’s a lovely spot to slow down, especially if you’re looking for a peaceful moment to connect with the town’s spiritual history.
6. Explore the Diocesan Museum: Art and History in One Place
If you’re looking to dive deeper into Cortona’s artistic and religious heritage, make sure to visit the Diocesan Museum of Cortona, just a short walk from the Duomo. Housed in a former palace, the museum displays an incredible collection of sacred art, much of which was created by local artists or commissioned for the town’s churches.
You’ll find works by famous artists like Fra Angelico and Luca Signorelli, making it a perfect stop for art lovers. I was particularly drawn to the stunning frescoes and paintings that bring Cortona’s religious and cultural history to life. It’s a place where history, art, and spirituality beautifully converge — and a great spot to reflect on the town’s deep-rooted connection to its artistic past.
The entrance ticket is 6 €. For more info check out the official website.
7. St. Francis and the Church of San Francesco
Cortona is also known for its spiritual heritage, and a visit to the 13th-century Church of San Francesco is a must. This church holds relics of St. Francis of Assisi, including his tunic, the cushion on which the dying saint led his head, and the New Testament he used. Brother Elias of Cortona, a close associate of Saint Francis of Assisi, brought these items to Cortona after the death of St Franicis of Assisi in Assisi.
However, the most valuable item of the church is the Reliquary of the Holy Cross (a piece of the True Cross on which Jesus of Nazareth was crucified) in a reliquary of Byzantine work in ivory and silver – making the Church of San Francesco in Cortona a place of pilgrimage for many.
The quiet, reflective atmosphere of the church is the perfect place to take a break from sightseeing and appreciate the spiritual side of Cortona.
8. Basilica of Santa Margherita: A Sanctuary with Stunning Views
Another iconic spot in Cortona is the Basilica of Santa Margherita, dedicated to the town’s patron saint, St. Margaret. Perched on a hill just outside the town center, the basilica offers breathtaking views of the entire region. The sight of the rolling Tuscan hills from here is absolutely mesmerizing — and there’s something truly serene about the place.
Inside the basilica, you’ll find the tomb of St. Margaret, and the peaceful atmosphere makes it an ideal spot for quiet contemplation. The walk up to the basilica is worth it just for the view alone, so make sure to include it on your itinerary.
9. Girifalco Fortress: A Piece of History and Panoramic Views
For a bit of adventure and even more stunning views, head to the Girifalco Fortress, a 16th-century military stronghold perched above Cortona. The fortress was built over the 5th/6th-century fort from Etruscan times. The fortress is only a few meters above the Sanctuary of Santa Margherita. It is a fantastic spot for history lovers and photographers alike, offering panoramic views of the town and the surrounding countryside. You can even see Lake Trasimeno in the distance from the fortresses on a clear day! It’s a bit of a climb to get to the top, but trust me — it’s worth it.
The fortress also gives you a sense of Cortona’s historical importance as a strategic location. Walking through the old stone walls and imagining what it must have been like during its heyday is an experience you won’t forget.
Click here to check out the timetables and fares.
10. Visit the Convent of Le Celle: A Tranquil Escape
If you’re looking for a place to experience the deep spirituality of Cortona, don’t miss the Convent of Le Celle (Convento delle Celle). Just a 10-minute drive from the town center, this peaceful sanctuary tucked into the hills offers an entirely different kind of experience.
St. Francis of Assisi spent time in prayer and contemplation there briefly in the early 13th century. Hermitage ‘Le Celle’ (Eremo Le Celle) founded Elias of Cortona, a close associate of St Francis of Assisi, adding a refectory and a few more rooms to the room where St Francis stayed. Convent de Le Celle is my favorite site in Cortona Italy. It is a place of supreme tranquility combined with the superb beauty of nature!
The serene atmosphere here is palpable, with the natural beauty of the surrounding forest adding to the sense of peace. You can explore the small chapel and the room where St Francis of Assisi once stayed, walk along the trails, and imagine what it must have been like for St. Francis as he lived here in solitude. For anyone looking to disconnect and find quiet, this is an essential visit — a true escape from the hustle and bustle.
11. Take in the View from Villa Bramasole: A Film Lover’s Dream
For a truly unforgettable experience, take a short trip outside the town to visit Villa Bramasole, famously featured in the book and film Under the Tuscan Sun. While the villa itself is private, the view from its grounds is nothing short of spectacular. From here, you can enjoy sweeping views of Cortona and the surrounding hills, perfectly framed by cypress trees and olive groves.
Even if you can’t visit the villa up close, just standing at a vantage point near the property and imagining Diane Lane walking through the gardens is a magical experience for any film lover. It’s one of those iconic Cortona moments that will stay with you long after you leave.
12. Sample the Local Flavors: Wine and Cuisine
What would a visit to Tuscany be without indulging in the region’s amazing food and wine? Cortona is renowned for its wines, particularly the Cortona DOC, made from Syrah and Sangiovese grapes grown in the nearby vineyards. Take time to visit a local winery, like Cantina Baldetti and Cantina Canaio, and sample some of the best wines in the region — the flavors will stay with you long after the last sip. Touring Cortona wineries is even a popular day trip from Florence. Check out the Exclusive Cortona Tour, Land of Tuscan Syrah.
And when it comes to food, you’ll be treated to some of the most delicious, rustic cuisine in Italy. Think rich pasta dishes, freshly baked bread, olive oil straight from the groves around town, and hearty meat dishes that are perfect after a day of exploration. Whether you’re sitting down at a family-run trattoria or enjoying a meal al fresco in the town square, you’ll be in for a real treat. A glass of wine, some pappardelle al cinghiale (wild boar pasta) or delicious crostini toscani, and a sunset over the hills? It’s as perfect as it sounds.
Where to Eat in Cortona: Restaurant Recommendations
- Osteria del Teatro: This cozy restaurant is a local favorite, offering authentic Tuscan cuisine and a great selection of wines. It’s a perfect spot for a romantic dinner or a relaxed meal with friends.
- La Bucaccia – Da Romano: Located in the heart of Cortona, this charming restaurant serves up classic Tuscan dishes in a warm, rustic atmosphere. Their wild boar ragu and steak are particularly popular.
- Caffè degli Artisti: If you’re looking for a casual, charming spot for a morning coffee or a light lunch, this café offers a great ambiance and a selection of delicious pastries.
13. Take a Cooking Class: Learn to Make Pasta and Pizza Like a Local
No trip to Tuscany would be complete without indulging in its incredible cuisine, and what better way to dive deep into Italian food culture than by taking a cooking class in Cortona? There are several local cooking schools offering hands-on experiences where you can learn to make fresh pasta and wood-fired pizza, two of the region’s most beloved dishes.
I highly recommend joining a class where you can roll up your sleeves, learn the secrets of making pasta from scratch, and bake pizza in a traditional stone oven. The best part? You get to enjoy your creations afterward, savoring the delicious results of your hard work while enjoying the rustic atmosphere of a typical Tuscan kitchen. It’s a memorable and immersive way to experience the local culture and gain skills that will impress your friends and family when you return home. Check out the Cortona: Pasta and Pizza Cooking Class.
14. Shopping in Cortona: A Treasure Hunt for Unique Finds
If you’re a fan of shopping, Cortona won’t disappoint. The town is full of charming little boutiques and artisan shops where you can find one-of-a-kind treasures. Whether you’re looking for handmade leather goods, vintage jewelry, or local ceramics, Cortona is the perfect place to find a piece of Italy to take home with you.
I was particularly taken with the quaint craft shops selling hand-painted pottery (like Clelia Tondini – Cortona Pottery Studio and Terrabruga), which make for perfect souvenirs. You can also find small artisan stores selling everything from handcrafted shoes to Tuscan linen, each item echoing the local traditions and craftsmanship.
Don’t forget to stop by the antique shops scattered around the town. These hidden gems are perfect for discovering rare vintage items and unique antiques. It’s a fun way to explore the town’s history and take a little piece of it home with you.
15. Attend the Archidado Joust: A Step Back in Time
If your visit coincides with the Archidado Joust, you’re in for a real treat. This historical event takes place every June and is Cortona’s most exciting and colorful celebration. The Joust is a medieval-style competition where locals dressed in historic costumes reenact the town’s past with a tournament of archery, sword fighting, and other exciting activities.
The joust brings the streets of Cortona to life, and you’ll feel like you’ve stepped into a time machine. It’s a fantastic way to immerse yourself in the town’s history and culture, and the excitement of the event is contagious. If you’re lucky enough to be in town during the joust, make sure to grab a seat in one of the piazzas and cheer on the contenders. It’s an unforgettable experience that will make your trip to Cortona even more special.
What is Cortona famous for?
Cortona is famous for its well-preserved medieval architecture (ancient stone buildings, churches, and piazzas), breathtaking views, and scenic landscape. The town is perched on a hilltop, offering sweeping vistas of the Val di Chiana and Lake Trasimeno.
Cortona gained international fame as the setting for Frances Mayes’ memoir Under the Tuscan Sun, later adapted into a popular film starring Diane Lane. The Villa Bramasole, featured in the movie, is located just outside Cortona and has become an iconic symbol of the town.
The town is also known for its deep Etruscan roots (the town dates back to the 7th century BCE). It was an important Etruscan city. One of the most famous artifacts found in Cortona is the Tabula Cortonensis, an Etruscan bronze tablet displayed in the Etruscan Museum today.
Besides that, Cortona has a big religious and spiritual significance. Cortona has strong ties to St. Francis of Assisi, who spent time in the Convent of Le Celle, a peaceful retreat that can still be visited today. His relics are also kept in the Church of St Franicis of Assisi in Cortona. The same church in Cortona keeps a piece of the True Cross of Jesus of Nazareth.
Where is Cortona?
Located in the eastern part of Tuscany, Cortona is perched on a hilltop in the province of Arezzo, overlooking the Val di Chiana. Its location offers some of the best panoramic views in all of Tuscany — rolling hills dotted with olive groves and vineyards as far as the eye can see. Cortona is about 120 km southeast of Florence, 30 km north of Perugia, and 25 km from Arezzo, making it a perfect base for exploring the heart of Tuscany and Umbria.
Distances from Cortona to nearby towns:
- Florence: 120 km (around 1.5 hours by car)
- Arezzo: 25 km (30 minutes by car)
- Perugia: 30 km (40 minutes by car)
- Siena: 90 km (1 hour 30 minutes by car)
How to Get to Cortona: Renting a Car is Key
While Cortona does have a train station, the most convenient way to explore this stunning part of Tuscany is by renting a car. Tuscany’s charm is best experienced through leisurely drives along its winding roads, and Cortona is no exception. Renting a car will give you the flexibility to explore not only Cortona but also the beautiful surrounding towns, vineyards, and countryside at your own pace.
If you’re flying in, the nearest major airports are:
- Florence Airport (Amerigo Vespucci Airport) — about 1.5 hours by car. Check out rental cars at Florence Airport.
- Perugia San Francesco d’Assisi Airport — about 45 minutes by car. Browse rental cars at Perugia Aiport.
- Pisa International Airport — about 2.5 hours by car. Check out rental cars at Pisa Airport.
I flew into Pisa Airport, rented a car, went to hike Cinque Terre first, and then went to Tuscany and Cortona. This was not my first Tuscany road trip. Driving in Tuscany is a pleasure — the roads are generally well-maintained, and the scenic views make every drive feel like a mini adventure. Just be aware that in some towns, like Cortona, the historic center is a pedestrian zone, so you’ll need to park outside the town and walk in.
Optionally, you could visit Cortona on a day trip from Florence or a day trip from Rome.
How Much Time Should You Spend in Cortona?
Cortona is the perfect size for a 2- to 3-day visit. You’ll want enough time to explore the town’s charming streets, visit its historic sites, enjoy its delicious food, and take in the stunning views. If you’re planning to do some nearby day trips (which I highly recommend), a longer stay would be ideal.
What to Do Near Cortona: Day Trips and Exploring the Region
While Cortona itself is a treasure trove of things to do, the surrounding region also offers incredible opportunities for exploration. Here are some fantastic day trips to take from Cortona Italy:
- Arezzo: A historic city just 30 minutes away, Arezzo is known for its beautiful medieval and Renaissance architecture, as well as the Piero della Francesca frescoes in the San Francesco church. Read: Top Things to Do in Arezzo
- Lake Trasimeno: Only 20 minutes from Cortona, this serene lake offers opportunities for boat rides, hiking, and enjoying the charming lakeside towns like Castiglione del Lago.
- Pienza: A UNESCO World Heritage Site, this Renaissance town is famous for its pecorino cheese and stunning views of the Val d’Orcia. Read: A Complete Pienza Travel Guide.
- Montepulciano: Famous for its Vino Nobile wine, Montepulciano is a must-visit for wine lovers. The town also offers panoramic views of the Tuscan countryside. Read: Best Things to Do in Montepulciano
When Is the Best Time to Visit Cortona?
The best time to visit Cortona is in spring (April to June) and early fall (September to October). During these months, the weather is pleasant, the crowds are smaller, and the landscape is at its most beautiful — lush and green in the spring, or golden and ripe with harvest in the fall. The summer months (July and August) can be quite hot and crowded, especially with tourists.
Is Cortona Worth Visiting?
Absolutely! Cortona offers everything you could want from a Tuscan town: rich history, stunning views, delicious food, and a relaxed, welcoming atmosphere. Whether you’re a history buff, a foodie, or simply someone who loves the charm of a small Italian town, Cortona is worth every moment of your time. It’s the kind of place that stays with you long after you leave.
Cortona is a hidden gem of Tuscany — peaceful, authentic, and full of life. So, if you’re planning a road trip through Tuscany, be sure to put Cortona on your list. You won’t regret it.
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