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Cortona

Day trips

Our most recommended Cortona Day Trips

From Florence: Assisi and Cortona Full-Day Guided Tour

1. From Florence: Assisi and Cortona Full-Day Guided Tour

Head out from Florence into the rolling green hills of Tuscany and Umbria to discover the architectural jewels of Assisi and Cortona. Your 11-hour tour begins in Assisi, the home of San Francesco. Your guide will lead you along the narrow, winding streets of the medieval town as you learn about its history. Inside the Basilica of San Francesco d’Assisi you’ll admire Giotto’s frescos of the life of San Francesco and discover why this is such an important pilgrimage site. See the interior of the Basilica of Santa Chiara, dedicated to a follower of San Francesco. Afterwards you’ll have free time for a stroll around this mystical city. Your tour will then continue with a visit to Santa Maria degli Angeli Church, the birthplace of the Franciscan Order. Cross back into Tuscany to the town of Cortona, built by the Etruscans, and noted for its architectural wonders and panoramic views over the surrounding landscape. Cortona is also well known as the setting for the movie, Under the Tuscan Sun.

Cortona: 2-Hour Private Walking Tour

2. Cortona: 2-Hour Private Walking Tour

Discover the iconic Tuscan town of Cortona, which was made famous in the book Under The Tuscan Sun by Frances Mayes. Located between Florence and Rome, Cortona is rich in Etruscan roots. It is an easy city for everyone to love due to its atmosphere, its Etruscan past, its delightful medieval old town, and its splendid panoramas. Your guide will help you admire this fantastic village throughout a private 2-hour tour, informing you of the secrets and history of the area. The path through the center of Cortona will lead you through the town's historical core, helping you discover the most important historical and artistic beauties of the city. You'll also discover the museums, walls, and buildings, throughout an exciting journey that will take you back throughout the centuries. The itinerary throughout this tour is not particularly demanding, and is suitable for the whole family.

Private Tour From Florence to Cortona and Montepulciano

3. Private Tour From Florence to Cortona and Montepulciano

Meet your English-speaking driver at your hotel on a comfortable Mercedes-Benz to start the journey to the beautiful Cortona. Enclosed by stonewalls dating back to Etruscan and Roman times, Cortona sits on the top of a hill. This dominant position over the valley offers a spectacular view from all over the town of the surrounding valley and even Lake Trasimeno. The town has become very popular in the past decade thanks to the book by Frances Mayes, Under the Tuscan Sun (and the movie with Diane Lane) which is set in Cortona. You will have time to relax or explore the area, the driver will suggest the best things to do in the area.  Leave at 11:30AM for have a delicious light lunch at a family winery. Continue then to Montepulciano on a relaxing 30 minute drive on the hills surrounded by breathtaking landscapes. Of course your driver can stop the car at anytime you want if you wish to take photos. Arrive at the charming Montepulciano around 2:00PM. This is a medieval hill town of rare beauty full of elegant Renaissance palaces, ancient churches, charming squares and hidden corners. Montepulciano has received lots of attention following the filming of the vampire saga Twilight sequel New Moon here and has seen a notable increase in visitors. A walk through Montepulciano is the best way to view the town as well as enjoy stunning views of the surrounding countryside covered by vineyards producing the famous Nobile which is possible to taste in the many wine shops located within the city's walls.

From Florence: Private Day Trip to Assisi and Cortona

4. From Florence: Private Day Trip to Assisi and Cortona

Discover the picturesque towns of Assisi and Cortona on this relaxing day trip from Florence. Explore Assisi's many churches, medieval castles, and the Roman amphitheater, and then wander through Cortona's famous Piazza Garibaldi. Meet your driver outside your Florence hotel and enjoy the stunning views as you drive through the countryside from Tuscany to Umbria. In Assisi, enjoy a stroll through this UNESCO World Heritage Site. Stop to admire the ancient Basilica of San Francesco d'Assisi and the Santa Maria Maggiore. After seeing all that Assisi has to offer, enjoy a relaxing lunch in town before rejoining your driver and heading to Cortona. This hilltop town is rich in Etruscan relics, medieval buildings, and Renaissance works. See parts of the original Etruscan wall, explore where Hannibal's army ambushed the Romans, and visit the Piazza Garibaldi. After sightseeing, enjoy a glass of wine with breathtaking views of Lake Trasimeno. When you're ready, let your driver know and return to Florence.

Cortona and Arezzo: Full-Day Tour from Rome

5. Cortona and Arezzo: Full-Day Tour from Rome

During the tour, you can explore the narrow and charming streets of Cortona and you can visit the most picturesque and hidden corners of this beautiful and unusual town. Together with your guide, you will also be able to retrace the places of the movie "Under the Tuscan Sun" and take a look at the famous Villa Bramasole.  After Cortona, you can visit Arezzo, another beautiful Tuscan town and one of the richest of the region, situated at the top of a hill. Here you will see the Basilica of San Francesco, well known for its wonderful cycle of frescoes and the "Legend of the True Cross" a masterpiece by Piero della Francesce. Also visit the city's cathedral, with its beautiful stained glass windows and the Piazza Grande, famous for being the set of Roberto Benigni’s movie "Life is beautiful".

Frequently asked questions about Cortona Day Trips

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Other Sightseeing Options in Cortona

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What people are saying about Cortona

Overall rating

4.9 / 5

based on 17 reviews

This was a great day. Massimo was an incredibly good guide for the day long excursion. Provided myself and my children so much in the way of historical and current context around what we saw and experienced, advice about what to spend time on, what not to waste time on and provided us space to explore alone and encounter the unexpected. The van was incredibly comfortable. Massimo even went above and beyond and helped us with dinner plans. He treated us like friends rather than clients. When we return to Italy we will use him again!

These Tuscan towns are breathtaking, I need to win the lottery to move here and enjoy the beauty, the people, the history, culture, charms and love these towns have to offer. Barbara was a wonderful guide who was always very attentive to our needs. Katia our local tour guide in Assisi is a great person. Her passion for such culture and history shows in all her explanations. Thank you Barbara and Katia.

Debra was Wonderful!!! She had a great knowledge of the area, introduced us to the nuances of Cortona and met several shop owners.

Great!!! Fantastic!!! Complete!!! There's nothing more to say.

The cities are beautiful and the guides are very good and cordial