Top 10 Private Tours in Cortona, Tuscany

April 14, 2022 Tambra Mccollister

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. Private Tour: Montalcino Wine Tasting Experience

52044 Cortona, Province of Arezzo, Italy Do it in Tuscany - Tours & Services
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5.0 based on 2 reviews

Private guided wine tour and tasting in Montalcino, Tuscany to discover Brunello and the most amazing wine estates and cellars that give birth to this extraordinary wine.

Inclusions: Lunch, Wine tasting, Snacks, Tour escort/host, Private tour, Round-trip private transfer (province of Siena and Arezzo)

Exclusions: Gratuities, Hotel pickup and drop-off outside of Siena and Arezzo province - to be quoted

Reviewed By bjhtmh

We spent a week in Cortona, in August 2019. Our guide was Francesco, who was amazing. We toured wineries, churches, museums, countryside and villages. Francesco arranged tours and transportation, and all we did was enjoy! We can't wait to get back.

2. 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.

3. Private Tour: MONTEPULCIANO Wine Tasting Experience

52044 Cortona, Province of Arezzo, Italy Do it in Tuscany - Tours & Services
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5.0 based on 2 reviews

Private guided wine tour and tasting in Montepulciano, Tuscany to discover Nobile and the most amazing wine estates and cellars in town and in the wonderful countryside,famous for its rolling and soft hills, vineyards and olive groves.

Inclusions: Lunch, Wine tasting, Snacks, Tour escort/host, Private tour, Alcoholic Beverages

Exclusions: Gratuities, Hotel pickup and drop-off outside of Siena and Arezzo province - to be quoted

Reviewed By smolly7

Having arrived in the Cortona area with very little planned I researched a few things to do. Finding this fabulous company was wonderful after emailing late (very late) on a Saturday evening Federica made everything happen seamlessly for a 10am pick up the following morning. We were met by a passionate bundle of energy called Francesco who proceeded to give us a fabulous walk through history and the process of growth and harvest on the way to our first stop. Francesco’s knowledge of the regions and the individual wines was extensive. He was and engaging and patient with our questions. Each vineyard was a contrast to the next, in regards to the process of winemaking. We were throughly relaxed and the day was full of laughter from start to finish. We truely can’t thank the team enough for giving us such a fabulous insight into the regions wines and countryside. If you’re ever in the area allow this business to look after you it is a must while in Tuscany. Ciao????

4. Arezzo and Cortona with wine tasting

Piazza dei Cavalleggeri, 50122 Firenze FI, Italy Flow Traveling
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5.0 based on 1 reviews

A full-day tour in Arezzo and Cortona to learn about a very beautiful area of the Tuscany region. The tour starts in Valdarno, with its spectacular countryside, vineyards and unique view. Enjoy a delicious wine tasting in a unique wine estate in the heart of Tuscany. Lose yourself in the medieval Arezzo, house of artists and poets, walking in the famous Piazza Grande and visiting the Gothic cathedral. This small city is home to many Italian secrets and traditions. Move to Cortona, a beautiful Etruscan city known for its archaeological remains. Two kilometers of the Etruscan walls, which date to the 5th century BC, are still standing today.

Inclusions: Wine and oil tasting with bruschette, Free time to visit Arezzo, Free time to visit Cortona, Air-conditioned vehicle, Private transportation

Exclusions: Gratuities

Reviewed By oliviajimenez1

It was such a beautiful day. Got home a bit tipsy, we had an amazing time drinking wine and walking in the gorgeous Chianti! Highly recommended

5. 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.

6. Private AREZZO and CORTONA Tour by Van from Florence

Piazza Adua, 50123 Firenze FI, Italy ACCORD Italy Smart Tours & Experiences
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2.0 based on 1 reviews

A full day to visit Arezzo and Cortona, another beautiful experience to learn about a very beautiful area of the Tuscany region. After only one hour drive to Arezzo by car or minivan, you will walk through the narrow streets to visit the city centre. Have you seen the  Oscar Film ” La Vita è Bella ” by Benigni? This is exactly the same!!! In the afternoon arrive in Cortona, one of the best Etruscan City. Do you remember the Book and Film " Under the Tuscan Sun "? Right here

Inclusions: Chauffeured air-conditioned vehicle 8 hrs, 2-hour stop in Arezzo, 2-hour stop in Cortona, English-speaking driver, Professional guide in Arezzo - 2 hours, Headsets to hear the guide clearly

Exclusions: Food and drinks

Reviewed By sandyc17

My husband and I did this tour and it was fabulous - the driver was great and there were only four of us so you could talk away to the driver - we scooted through the city easily on the golf cart and it was such good fun and we saw loads of amazing stuff, I’d highly recommend this tour

7. 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.

8. Assisi, Deruta & organic gourmet lunch at the olive oil farmhouse from FLORENCE

We Drive You Tuscany

- Go on an artistic, spiritual quest to Assisi and discover the divinity in the air and in Giotto's brushstrokes, which depict the life of Saint Francis in Assisi's Basilica. - Experience the exceptional, the sublime, the mesmerising, all at one time in one place. - Take your lunch in an intimate, local restaurant/farmhouse, with a glass of Montefalco Red or Sagrantino ready at hand for a toast. - Experience the local extra virgin olive oil production. - Delight in Deruta, where you will encounter extraordinary ceramics and have the chance to visit Ubaldo Grazia, the world's most ancient majolica factory. * Private, Exclusive, Customizable, door-to-door tour of Umbria, wine and food Tour from Florence.

Inclusions: Private tour, Hotel pickup and drop-off, 9 hour door-to-door tour in a luxury Mercedes vehicle and knowledgeable English speaking driver, Free Wi-Fi on board, Refreshments on board, Gas - Tolls - VAT

Exclusions: Eventual entrance fees, Lunch, Sagrantino di Montefalco wine tasting + visit

Reviewed By 611lassed

We booked a wine tour for half a day only the night before and received the confirmation following morning! The driver picked us up at our place in Siena with a very nice and comfortable car. Our driver was Roberto, who spoke very well English and is a very funny and nice guy! He could answer all our questions on Italian cuisine and culture in a very passionate way. The wineries we visited were as authentic as you could imagine and they let us try all their best wines! We had an amazing afternoon and wished we’d booked for the entire day. Wedriveyou.it is highly recommended by us and make sure you ask for Roberto!

9. Private tour from Florence to Cortona and Arezzo

Tuscany in Tour

Enjoy this two wonderful hilltop towns on a full-day and discover historic architecture, artwork, and neighborhoods with views of the Tuscan countryside. Take in film locations from ‘Under the Tuscan Sun’ (Cortona) and ‘Life is Beautiful’ (Arezzo) as you spend the day with our knowledgeable driver, exploring Tuscany at its most picturesque.

Inclusions: Driver/guide, Hotel pickup and drop-off

Exclusions: Lunch, Gratuities

Reviewed By Darknightaz

Massimo picked us up on time at the hotel and we spent a wonderful day exploring Montalcino and Montepulciano. He was friendly and knowledgeable. The tour was well paced and included visits to two wineries. I would recommend to anyone interested in a private tour of the Tuscan countryside.

10. Cortona and Montepulciano Tour From Rome

Discovery Tours Limousine Service Day Tours

A visit to Cortona and Montepulciano is a special encounter with history, great food, and high quality wine. Cortona lies far atop a hillside dominating the south side of the Chiana Valley. From there you will enjoy magnificent views of Lake Trasimeno and the surrounding forests, along with vineyards and olive groves that produce some of the best wine and olive oil in all of Italy. After Cortona, you will continue your journey by visiting the hill town of Montepulciano, home of the famous “Vino Nobile di Montepulciano,” a wine that originated in the 1300s. Another fascinating attribute of Montepulciano is that it is one of the only places in the world where there are ancient underground cellars, right in the heart of the town, that date back to Etruscan times. We will leave Montepulciano, saying goodbye to its beauty, and start the drive back to Rome.

Inclusions: Pick up/drop off , A fun and informative private English speaking tour driver , Private transportation, fresh bottled water on board, Parking, city passes, fuel & tolls

Exclusions: Meals & entrance fees (unless specified on your confirmation voucher), Gratuities (entirely at the client’s discretion), Wine Tasting - Additional Cost approx 20 € per person

Reviewed By R8876FNjons

Gilberto and Max of Discovery Tours provided the day trip of a lifetime to Anzio where I followed in my father's footsteps to see where he served his country in World War 2. Discovery Tours handled all the logistics, trip planning and detailed information on the battle sites and Anzio campaign with consummate professionalism. I learned much and thanks to Gilberto and Max, have a much deeper and personal understanding of the challenges my father and all other servicemen and women faced during this critical time in history. I enthusiastically recommend Discovery Tours to enrich your travel experience in the wonderful country of Italy.

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