Private Art & Wine Tour in Cortona & Montepulciano, with lunch & 2 wine tastings

Arezzo , Italy

Private Art & Wine Tour in Cortona & Montepulciano, with lunch & 2 wine tastings

Active

For a full refund, cancel at least 24 hours before the scheduled departure time.

Instant confirmation

Mobile or paper ticket accepted

About this experience

Follow the trail of the film "Under the tuscan sun". We will take you to the rolling Tuscan landscape, among vineyards, art and sunflowers. We will visit the countryside and the city of Cortona, "the secret underground cellars" of Montepulciano. You will taste the best wines of our region and have a typical Tuscan lunch. Itineraty:
• We will explore southern Tuscany and visit the medieval city of Cortona and the Monastery of San Francesco called "Le Celle"
• We will stop to take photos of the landscape along the road featured in the film "Under the Tuscan Sun"
• Later we will visit the "Underground Wonders" of Montepulciano (The Historic Cellars of the city) where you will find gigantic oak barrels, in which the famous Vino Nobile di Montepulciano DOCG "rests".
• In Montepulciano we will have a delicious lunch and two wine tastings in two different cellars.
The return is scheduled for 5pm

Available options

Private Art & Wine Tour in Cortona & Montepulciano, with lunch & 2 wine tastings

Pickup included

What's included

Private transportation

2 Wine tastings included in 2 differet local Wineries (Nobile of Montepulciano and Red of Montepulciano Docg tastings)

3 Course lunch to a real Historical Cellar in Monteplciano, to understand the secrets of wine production and enjoy a lunch homemade pasta, cold cuts, Pecorino Cheese and Bruschettas)

Bottled water

Local expert driver and tour leader

Air-conditioned vehicle

All inclusive tour

Detailed itinerary

Our expert driver will pick you up at your hotel or other chosen location (B&B or private apartment) and take you to discover the Tuscan countryside. The first stop will be in Cortona for a self-guided visit of the city (1 hour). Cortona is a traditional fortified Etruscan city, located approximately 600 meters above sea level, offering spectacular views of the surrounding valley and Lake Trasimeno. The main things I recommend you look for in the city center are: - Piazza della Repubblica, the historic center of Cortona - the pretty medieval streets of Cortona - Piazza Signorelli - the beautiful shops of Cortona, We will also visit the incredible Monastery of St. Francis, a peaceful place not far from the city.

After leaving Cortona, we will stop to take photos of the landscape along the road described in the film "Under the Tuscan Sun". Afterwards we will head to Montepulciano to visit the "Underground Wonders" of the city. We will visit the main square of the town (Piazza Grande), the ancient Government Palace and two historic cellars: here you will find gigantic oak barrels, in which the famous Vino Nobile di Montepulciano DOCG and Rosso di Montepulciano DOC rest.

In the heart of Montepulciano, you will enjoy a delicious Tuscan lunch and five wine tastings following a guided tour of a historic underground cellar located in the old town.
The experience includes:
• Guided tour of the historic cellar
• Wine tasting of:
o Rosso di Montepulciano DOC
o Nobile di Montepulciano DOCG
o Nobile di Montepulciano Riserva DOCG
o Nobile di Montepulciano “Filai Lunghi” DOCG or IGT “Pietrose” Super Tuscan
Lunch includes:
• Homemade pasta (Pici, Lasagne, or Cannelloni)
• Pecorino di Pienza cheese
• Typical Tuscan cured meats (ham, loin, salami)
The cellar is a spectacular historic site carved directly into the ancient rock beneath Montepulciano’s historic center. Its underground tunnels open into large chambers where the Nobile di Montepulciano wines are aged, offering a truly atmospheric and authentic experience.

The second wine tasting experience will take place in a historic underground cellar. During the Renaissance, the family who owned the estate cultivated vineyards, and by the 1700s this activity had earned widespread recognition. They are regarded as among the founding fathers of Vino Nobile di Montepulciano.

Following a visit to the cellar, you will enjoy a special wine tasting of 4–5 wines.

At the end of the second tasting experience, we will return to your location.

What's not included

Everything not found under the heading inclusions is excluded

Available languages

Guide guide

EN IT FR ES

Important information

Specialized infant seats are available

Infants and small children can ride in a pram or stroller

Transportation options are wheelchair accessible

Suitable for all physical fitness levels

Wheelchair accessible

About Arezzo

Arezzo is a historic city in Tuscany known for its rich medieval and Renaissance heritage, beautiful architecture, and the famous Piero della Francesca frescoes. The city offers a charming blend of art, culture, and authentic Italian charm.

Top Attractions

Piazza Grande

The main square of Arezzo, Piazza Grande is a beautiful example of medieval architecture and a UNESCO World Heritage site.

Historical 1-2 hours Free

Basilica of San Francesco

This 13th-century basilica is home to the famous frescoes by Piero della Francesca, including 'The Legend of the True Cross'.

Religious 1 hour €5

Medieval Fortress (La Rocca)

A 14th-century fortress offering panoramic views of Arezzo and the surrounding countryside.

Historical 1 hour €4

Arezzo Cathedral

A beautiful cathedral with a mix of Romanesque and Gothic architecture, featuring works by Pietro Lorenzetti and Guglielmo dei Marcillat.

Religious 30 minutes Free (donations welcome)

Casa Museo Ivan Bruschi

A museum housed in a 13th-century palace, showcasing a collection of art and artifacts from the Middle Ages to the Renaissance.

Museum 1 hour €7

Must-Try Local Dishes

Bistecca alla Fiorentina

A thick-cut, grilled T-bone steak seasoned with salt and olive oil, typically from Chianina cattle.

Dinner Contains beef

Pici all'Aglione

Hand-rolled thick spaghetti served with a garlic and tomato sauce.

Dinner Vegetarian

Cantucci con Vin Santo

Almond biscotti dipped in a sweet dessert wine.

Dessert Contains nuts, contains alcohol

Popular Activities

Hiking in the surrounding countryside Cycling tours Wine tasting Spa treatments Visiting museums and churches Attending local festivals Participating in the Saracen Joust festival Exploring the antique market

Best Time to Visit

April to June, September to October

The best time to visit Arezzo is during the spring and fall when the weather is pleasant, and the tourist crowds are smaller. The city is vibrant with various festivals and events.

15-28°C 59-82°F

Practical Information

Language

Official: Italian
Widely spoken: English, French, German
English: Moderately spoken

Currency

Euro (EUR)

Time Zone

GMT+1 (CET), GMT+2 (CEST during daylight saving time)

Electricity

230VV, 50HzHz

Safety Information

Overall Safety Rating: Generally safe

Arezzo is generally safe for tourists, with low crime rates. However, as with any destination, it's important to be aware of your surroundings and take basic precautions.

Important Precautions:

• Keep valuables secure
• Be cautious of your surroundings
• Use licensed taxis

Getting there

By air

Florence Airport • 80 km
Perugia Airport • 90 km

By train

Arezzo Station

By bus

Arezzo Terminal Bus

Getting around

Public transport

The bus network is efficient and covers most parts of the city and surrounding areas.

Taxis

Available • Apps: FreeNow

Rentals

Car, Bike, Scooter

Neighborhoods

Historic Center San Lorenzo Porto San Marco

Day trips

Cortona

30 km • Half day

A charming hilltop town known for its medieval architecture, stunning views, and as the setting for the book and film 'Under the Tuscan Sun'.

Montepulciano

50 km • Full day

A beautiful Renaissance town famous for its wine, particularly Vino Nobile di Montepulciano, and its stunning architecture.

Val d'Orcia

60 km • Full day

A UNESCO World Heritage site known for its rolling hills, cypress trees, and picturesque villages, offering stunning landscapes and outdoor activities.

Festivals

Saracen Joust (Giostra del Saracino) • First Sunday in September and first Sunday in June Arezzo Antiques Fair • First Sunday of the month Arezzo Wine Festival • Late September

Pro tips

Visit the Basilica of San Francesco early in the morning to avoid crowds and enjoy the frescoes in peace
Explore the historic center on foot to discover hidden gems and charming side streets
Try local specialties like Bistecca alla Fiorentina and Pici all'Aglione at traditional trattorias
Attend the Saracen Joust festival if your visit coincides with the event for a unique and thrilling experience
Take a day trip to nearby towns like Cortona and Montepulciano for stunning scenery and historic sites