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Cortona
Walking tours

Walking tours

Our most recommended Cortona Walking tours

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.

From Florence: Siena, Cortona, Montepulciano & Val D'Orcia

2. From Florence: Siena, Cortona, Montepulciano & Val D'Orcia

Meet your local tour leader and the rest of your group of like-minded young travelers for a full day to discover the unbeatable paths of Tuscany made famous by movies. From Florence, travel for 1.5 hours by private 8-seat mini-van through the beautiful Tuscan countryside enjoyed by generations on the movie screen. Learn about the Italian way of life, the local customs, cuisines, and quirks from your guide before reaching the first stop of the day, Siena. Admire this medieval town that set the backdrop of the famous movies Letters to Juliet and Stealing Beauty. Be amazed by the charming narrow streets with local artisans, red-brick squares, and gothic cathedral. Then, continue the trip towards your next destination, the famous Montepulciano, where vampires converge in the Twilight Saga's New Moon. The beautiful walled town is also the home of the Montepulciano DOCG wine, making it the perfect opportunity for a tasting of vino and other local products at a 14th-century underground cellar. Have the chance to purchase products for the perfect gift or to ship home. Here, savor a wine tasting with a light lunch made with local products. Throughout the tour, your guide will provide you with local insight and information about the specific scenes and other films set in each place, as well as free time to explore the other attractions that the towns have to offer at your leisure. After lunch, head to Cortona, the luscious hilltop town known for its olive groves and made famous by Diane Lane in Under the Tuscan Sun. Spend some free time in Cortona to explore the narrow streets, artisan stores, and other landmarks which are seen in the cinematic adaption of Frances Mayes' novel. Who knows, maybe your own Italian love story will unfold! Finally, head back to Florence for approximately 8 PM.

Cortona: Pasta and Pizza Cooking Class

3. Cortona: Pasta and Pizza Cooking Class

After enjoying a cup of espresso and getting to know each other, lunch or dinner preparations will begin. You'll get settled into the kitchen, get your aprons on and then get cooking! Your local cook Simonetta will teach you everything you need to know to make some delicious Pizzas and Fresh Pasta and she will assist you the whole time. From the beginning to the end, all steps in the process will be followed. After all the dishes are prepared and cooking, you will be able to enjoy a rest by walking in the garden. From the garden you will enjoy a 360 degree panoramic view of the Valdichiana valley. The garden is beautiful, and full of a wide variety of roses that you'll be able to enjoy as you stroll around the gardens. When the weather is nice, lunch or dinner can be served on the terrace so you can admire the sunset (in case of dinner) over the Tuscan hills, accompanied by the chirping of birds. Of course, you will also be able to enjoy a good glass of wine from the wine list of over 85 local Tuscan wines.

Cortona: Guided E-Bike Tour of Tuscany's Hidden Gem

4. Cortona: Guided E-Bike Tour of Tuscany's Hidden Gem

In Cortona, discover the village where nature and history combine with incredible views that will be the setting for a beautiful e-bike ride to discover areas little known for mass tourism. Just as it was for the Etruscans, Cortona is still located in a strategic position that allows with low effort, to visit historical places and admire breathtaking views. This route will be familiar to locals, but difficult to plan without a guide. I will tell you about the many intriguing stories of this area, from the old lake, the maps of the surrounding area by Leonardo da Vinci and the numerous battles fought over control of the city. An e-bike ride is simple and suitable for everyone. An easy bike ride makes it easy to focus on your surroundings and make the most of the ride. The guide will take a few minutes before we start to explain how to use the eBike and to make your bike safe and fun. If you're looking for other guided tours in the area, don't worry. In addition to Cortona, you can find similar experiences in Cortona - Valley, Arezzo, Pienza, and Castiglion Fiorentino. And if you desire a personalized experience, simply contact us, and we'll create a tailor-made tour just for you. Don't miss the opportunity to have a unique and unforgettable experience in beautiful Tuscany!

Cortona: Valdichiana Guided eBike Tour +option wine tasting

5. Cortona: Valdichiana Guided eBike Tour +option wine tasting

As we embark on our e-bike tour through the charming Val di Chiana, we'll witness the sublime beauty of the Tuscan countryside that stretches between Cortona and Montepulciano. During the tour, we'll have the opportunity to distinguish between the unique characteristics of Val di Chiana Aretina and Val di Chiana Senese, as we venture along peaceful white gravel roads, far from the commotion of traffic and tourists. Our tour will take us on a loop, affording us the chance to admire the flourishing wheat crops and immaculate vineyards that dot the landscape. As we meander through the countryside, we'll be greeted by vibrant wildflowers and breathtaking vistas that will leave us feeling as though we've stepped into a dream. On our way back, we'll visit a local farm and winery for a delightful wine tasting experience. Indulge in the region's finest wines paired with a light lunch, all for approximately €40 per person, payable directly at the winery. With our expert guide leading the way, you'll have the chance to discover all of these amazing landmarks and more during your e-bike tour through the Val di Chiana. So come and join us for an unforgettable journey through one of the most beautiful regions in all of Italy. If you're looking for other guided tours in the area, don't worry. In addition to this, you can find similar experiences in Cortona (up in the hill town), Arezzo, Pienza, and Castiglion Fiorentino. And if you desire a personalized experience, simply contact us, and we'll create a tailor-made tour just for you. Don't miss the opportunity to have a unique and unforgettable experience in beautiful Tuscany!

Cortona: Private 2-hour Guided Tour

6. 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.

Pienza: Guided E-bike Tour through the Val d'Orcia

7. Pienza: Guided E-bike Tour through the Val d'Orcia

Our e-bike tour through the Val d'Orcia also includes visits to some of the region's most iconic landmarks, including the 500-year-old Giardino in San Quirico. This stunning garden is a true masterpiece of Italian design and is sure to take your breath away. Another highlight of the tour is the visit to the Chapel of Vitaleta, a beautiful stone chapel that stands in a picturesque countryside setting. This iconic landmark has been featured in many postcards and photographs, and its beauty is truly awe-inspiring. As you continue your journey through the Val d'Orcia, you'll also have the chance to explore the Campi Elisi the most breathtaking and iconic landscapes in the region. These stunning fields are filled with colorful wildflowers, and their beauty is unmatched by anything else in the world. With our expert guide leading the way, you'll have the chance to discover all of these amazing landmarks and more during your e-bike tour through the Val d'Orcia. If you're looking for other guided tours in the area, don't worry. In addition to Pienza, you can find similar experiences in Cortona, Arezzo, Castiglion Fiorentino, and Montepulciano. And if you desire a personalized experience, simply contact us, and we'll create a tailor-made tour just for you. Don't miss the opportunity to have a unique and unforgettable experience in beautiful Tuscany!

Private Tour From Florence to Cortona and Montepulciano

8. 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: 3-Hour Private Walking Tour

9. Cortona: 3-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 3-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.

Arezzo and Province: Drive Vintage Vehicle with Audio Guide

10. Arezzo and Province: Drive Vintage Vehicle with Audio Guide

This tour is designed to familiarize you with places of historical and nostalgic significance. Many of the places available to discover on this tour are off-the-beaten path, and not commonly seen by tourists.  Start your adventure at the meeting point where you will get to choose your tour option, and the vintage vehicle you desire to drive. Pick the tour most suited to your needs and the car you've always dreamed of driving. Once you've picked your tour and vehicle, you will be required to successfully complete a driving lesson to familiarize yourself with the technical components of driving your vintage vehicle.  Once you have learnt the basics, you will be able to set-off, learning a lot about the places you drive past with your complimentary audio-guide. Your vehicle will be equipped with everything you need as you drive through quaint Tuscan towns and witnessing places of historical curiosity.

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Frequently asked questions about Cortona Walking tours

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What people are saying about Cortona

Overall rating

5.0 / 5

based on 1 reviews

Our guide Claudia made a great and informative tour. We recommend! The only negative comment was the time. The tour was only offered at 3:00 p.m. and that's just extreme at 32 degrees. We had booked another guided tour in Assisi, which was also only offered at 3:00 p.m., which we canceled.

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.