The 9 Best Walking Tours in Cortona, Tuscany

July 12, 2021 Mollie Coke

Perhaps best known these days as the setting for the book and movie “Under the Tuscan Sun,” gorgeous hillside Cortona has a long history dating back even before its time as an important Etruscan center. Top attractions include the Duomo (Cathedral), the small Museo Diocesano across the piazza with its superb art collection, and the fascinating Museo dell'Accademia Etrusca with its assembly of Etruscan and Roman era items. Cortona is also bursting with splendid churches spanning many periods.
Restaurants in Cortona

1. Cortona Private Guided Tour

Cortona Piazza Garibaldi, 52044 Cortona, Province of Arezzo, Italy Umbria Con Me Day Tours
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5.0 based on 1 reviews

Cortona has become very popular several years ago thanks to the book by Frances Mayes, Under the Tuscan Sun (and the movie with Diane Lane) which is set in Cortona; the protagonist immediately falls in love with the town, its people, and villa Bramasole that she purchases and fixes up.

Inclusions: Local guide

Exclusions:

Reviewed By D1271ETdianaw

We had a fascinating morning with Alessandra, exploring Assisi and learning about its history. It's such a beautiful place, and Alessandra made it come alive for us. The 'Umbria con me' attention to detail was superb, and booking lunch for us at a local restaurant afterwards was a lovely touch.

2. Siena, Cortona, Montepulciano & Val D'Orcia from Florence - Semi private tour

Via Nazionale, 149, 50129 Firenze FI, Italy Italy on a Budget Tours
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5.0 based on 7 reviews

Explore in the comfort of a 8 seat van the most beautiful Tuscan towns made famous through films together with a passionate local driving guide. Enjoy lunchoverlooking the rolling hills of Montepulciano while tasting famous wine. Wander the winding streets of Cortona walked by Diane Lane in "Under the Tuscan sun", watch out for the vampires of the Twilight saga " New Moon" in Montapulciano and taste the famous Noble of Montepulciano wine. Explore the locations made famous by Michelle Pfieffer in "A Midsummer night's dream" and Ralph Fienes in " The English patient". Spot the iconic rolling hills of Tuscany from " Letters to Juliet" and enjoy a taste of the local lifestyle by sampling fine local wine, cheese and other products from the region.

Inclusions: Light lunch in a local winery including 2 wine tasting including the famous " vino nobile di Montepulciano", Wine and cheese tasting in a 13th century cellar, Air-conditioned vehicle, Orientation walk of Montepulciano and free time, 1h free time to explore Cortona, Orientation walk of Siena and free time

Exclusions: Gratuities, Pick up / Drop off

Reviewed By amrutaprasad029

Beautiful experience... We had booked the tour online and it was better than expected ... Beet well planned too ... And great guide

3. Private Full-Day Tour of Assisi and Cortona from Florence

Ciao Florence Tours and Travels
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4.6 based on 9 reviews

Relax on this private, full-day tour of Assisi and Cortona. Enjoy the personalized attention of your private driver and discover the place where St. Francis and St. Clare were born and visit the wonderful hilltop town of Cortona. A relaxing day trip between Umbria and Tuscany at your own pace! Hotel pickup and drop-off from Florence is included with a driver.

Inclusions: Hotel pickup and drop-off, Mercedes vehicle, Speaking driver, Free time in Assisi and Cortona, Bottled water, Wi-Fi

Exclusions: Food and drinks, Local guides in Assisi and Cortona

Reviewed By J Adam K

Took the walking tour today with Safe as our guide. Wonderful experience. Safe spoke flawless English and his passion for Florence, art and history was addicting. We hope to do something similar in the future.

4. Assisi and Cortona Day Trip from Florence

Piazzale Montelungo, Firenze FI, Italy Ciao Florence Tours and Travels
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4.1 based on 126 reviews

Discover the enchanting hilltop towns of Assisi and Cortona on a day trip from Florence, led by a local tour leader! Walk around Assisi, and learn about the life of St Francis of Assisi on visits to the Basilica of San Francesco and the Convent of Santa Chiara. Stop to admire the 9th-century church in Santa Maria degli Angeli before continuing to the Tuscan town of Cortona for some free time to explore.

Inclusions: Journey by fully fitted GT Coach, Expert multilingual escort, Assisi tour with professional guide, Stop for panoramic pictures at Passignano sul Trasimeno, Entrance fee to St Francis'Basilica, Entrance fee to Santa Chiara Church, Entrance fee to Santa Maria degli Angeli Church

Exclusions: Hotel pickup and drop-off, Food and drinks, Gratuities

Reviewed By J Adam K

Took the walking tour today with Safe as our guide. Wonderful experience. Safe spoke flawless English and his passion for Florence, art and history was addicting. We hope to do something similar in the future.

5. Taste of Italy Food Tour to Chianti and Umbria from Rome

Via Giovanni Amendola, 32, 00185 Roma RM, Italy Green Line Tours
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3.8 based on 246 reviews

Discover the foods, wines and hill towns of Tuscany’s Chianti wine region and Umbria on this engaging full-day tour from Rome! Accompanied by an expert local guide, travel through Tuscany’s rolling countryside and visit the lovely medieval town of Cortona, with time to explore its cobbled lanes and absorb its old-world atmosphere. Enjoy a tasty regional lunch at a rural farmhouse restaurant, and wind through the vineyards of Chianti to the hill town of Montepulciano. Here, sample some delicious local wines at a traditional cellar before heading back to Rome.

Inclusions: 4-course lunch, Local guide, Transport by air-conditioned coach (maximum 50 people), Hotel pick-up (only for certain hotels located in central Rome - to be reconfirmed by the supplier after booking)

Exclusions: Gratuities, Drinks with lunch (available to purchase)

Reviewed By nth1234

Wonderful tour of St Peters finishing with the cistine chapel with Alessandro. Once again this guide was first class in his delivery and knowledge of the place. Sean the boss of Angel Tours was excellent with his communications and I thoroughly recommend this company, will definitely use again.

6. Full-Day Private Walking Tour of Cortona

Camucia Stazione, 52044 Camucia, Province of Arezzo, Italy Tuscany Untouched

Take an 8-hour private walking tour through Cortona with a professional guide. Walk through a magnificent location nestled in the woods leading to the cells of St. Francis, enchanted and spiritual, then follow a path that leads to the highest part of the city where the fortress is located with its imposing walls. Have lunch in one the best restaurants in Tuscany, Locanda (own expense). A professional art historian guide will meet you after lunch to show you the history of this beautiful village, visiting the city's most impressive churches: San Niccolò and Santa Chiara (the second church built after the Saint's death). Once in the center of the city, take in the magnificent main square, rich in history and references to the Etruscan world. Then learn about the traditions of the place through the specialty shops of ceramics, local produce, and wine bars. Private tour is limited to 8 people.  

Inclusions: All taxes, fees and handling charges, Professional art historian guide, Environmental tour guide, Local guide, Private tour

Exclusions: Drinks, Alcoholic drinks (available to purchase), Food and drinks, unless specified, Gratuities, Hotel pickup and drop-off, Transportation to/from attractions, Lunch

Reviewed By frodo216

We loved the hot springs and the setting along a river in the woods and found a small pool at a perfect temeperature for a long soak. The wine tasting at a small family vineyard was a pleasant way to round out the day and a nice introduction to the wines of Montalcino. Matteo was and excellent guide and driver - we enjoyed his insights into the countyside and hid frindly and professional manner. Highly recommended.

7. Siena and Cortona full day private day trip from Perugia or Assisi

Umbria Con Me Day Tours

Get your Private day trip in Siena and Cortona and discover its culture, incredible sites, stories legends with entertaining and passionate professional guides. See the artistic, religious, and cultural treasures of Cortona and Siena with professional guides

Inclusions: Private car/van with driver, Guided tour of Cortona, Guided tour of Siena

Exclusions: Lunch, Gratuities, Admission fees

Reviewed By D1271ETdianaw

We had a fascinating morning with Alessandra, exploring Assisi and learning about its history. It's such a beautiful place, and Alessandra made it come alive for us. The 'Umbria con me' attention to detail was superb, and booking lunch for us at a local restaurant afterwards was a lovely touch.

8. Cortona private walking Tour

Piazza Garibaldi, 52044 Cortona AR, Italy Bologna Tour

Discover the iconic Tuscan town of Cortona (made famous in the book by Frances Mayes Under The Tuscan Sun). Located between Florence and Rome, Cortona is rich in Etruscan roots. Cortona is an easy city for everyone to really love. This is because its atmosphere, its Etruscan past, its delightful medieval old town and also its splendid panoramas.

Inclusions: Certified local guide, Bottled water

Exclusions: Private transportation

Reviewed By Tielemanis

As a Ferrari fan, this was a true highlight of my trip to Bologna - Maranello is such a magical place to be! The museum showed the beautiful history on the evolution of its brand! A day to remember!

9. ROME LUXURY TOUR: Cortona Private tour from Rome

Ticketinrome.com

Discover the iconic Tuscan town of Cortona (made famous in the book by Frances Mayes “Under The Tuscan Sun”). Located between Florence and Rome, Cortona is a city easy to love thanks to its timeless atmosphere, its Etruscan past, the delightful medieval old town and its splendid panoramas. Spending time walking through the streets is the main pleasure of a visit to Cortona and there are many historic buildings to admire while walking.

Inclusions: Certified Tourist Guide, Bottle of water, Private guided tour, Pick-up / Drop-off in Hotel, Free customer service 7/7

Exclusions: Food and Drinks (avalaible on request)

Reviewed By Leoz2020

The Agency was helpful in the booking office, but the purchased time slot was not available even though we had booked it in advance and paid. However they were able to give us an earlier time slot. The booking stated that the host accompanied us to the correct entrance at the colosseum. This didn’t happen and we where given verbal directions at the booking office which was about a 5 minute walk away. This wasn’t as advertised and I think was poor customer service. It added stress and hassle to the trip which I had paid to avoid. The booking details are inaccurate and should be changed to suit the actual service provided. The Colosseum itself was brilliant and awe-inspiring!

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