Cortona Private tours

Our most recommended Cortona Private tours

From Florence: Private Day Trip to Assisi and Cortona

1. 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: 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.

Cortona: Private 2-hour Guided Tour

4. Cortona: Private 2-hour Guided Tour

Cortona is a town which is certainly easy to love for everyone. This is mainly because of its atmosphere, its Etruscan past, its lovely medieval city center, and its fantastic views. Your experience begins as your professional local guide takes you on a private walking of the historical center of Cortona which will take you back in time. The tour features Piazza della Repubblica - the main square dating back to the Roman age, Palazzo del Capitano del Popolo - the residence of Cardinal Passerini during the 16th century, and the Palazzo Comunale - which dates back to the 12th century. Traveling further, encounter Palazzo Casali and Teatro Signorelli, which is a typical theater in a Neoclassical style still in use for the local theater season. The town’s cathedral will be also be a part of your walking tour, complete with its charming views.

Other Sightseeing Options in Cortona

Want to discover all there is to do in Cortona? Click here for a full list.

What people are saying about Cortona

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!

Our tour guide Giuseppe was one of the most informative we have ever experienced. His knowledge of art, history and culture made Cortona come alive for us and he was so funny and engaging that the time flew by! We highly recommend this experience.

An excellent guide who was a local resident was able to show us and give us an insight into the very quaint and interesting Cortona. Highly recommend a guided tour to see what makes this town so unique and unforgettable

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

Julia was a fantastic guide. I highly recommend this tour.