Private Tour Siena San Gimignano and Chianti from Cortona

Arezzo , Italy

Private Tour Siena San Gimignano and Chianti from Cortona

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(4 reviews)

8h - 9h

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

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Mobile or paper ticket accepted

About this experience

Kick off your day with a comfortable ride through the stunning Tuscan countryside. First, we’ll arrive in Siena, one of Tuscany’s most beautiful towns. Explore Piazza del Campo, famous for the Palio di Siena horse race, admire the breathtaking Duomo (Cathedral), and wander through the charming, narrow streets of the historic center. Wine Tasting & Light Lunch Next, we’ll head to a renowned winery for a light lunch paired with an amazing wine tasting experience. A sommelier will guide you through five exceptional wines, plus an olive oil tasting.
After lunch, we’ll continue our journey with a spectacular drive through the rolling Vernaccia di San Gimignano vineyards, home to Tuscany’s most famous white wine. Stop in San Gimignano you’ll have free time to explore this medieval gem, known for its 14 towers dating back to the 13th century. The town’s atmosphere will transport you back to the Middle Ages! And of course, you can’t miss the world’s best gelato at Gelateria Dondoli.

Available options

Private Tour Siena San Gimignano and Chianti from Cortona

Pickup included

What's included

Private transportation

WiFi on board

Bottled water

All Fees and Taxes

Air-conditioned vehicle

lunch in a family winery tour and tasting

Detailed itinerary

Stop 1

Piazza del Campo (or simply Il Campo) is the main square of Siena. Famous for its unique shell shape, it is known worldwide for its beauty and well-preserved architecture. It is also the site of the Palio di Siena, a horse race held twice a year. By ancient tradition, the square and the Palazzo Pubblico do not belong to any contrada.

Stop 2

The Siena Cathedral, or Cattedrale di Santa Maria Assunta, is one of the masterpieces of Italian Gothic architecture. Located in the heart of the city, it stands out for its extraordinary façade of white, dark green, and red marble, as well as its interior rich in artworks.

It is undoubtedly one of the most beautiful and most visited cathedrals in Italy.

Monteriggioni is a small medieval village in Tuscany, in the province of Siena. It is famous for its spectacular walls, making it one of the best-preserved fortified villages in Italy.

San Gimignano is a charming medieval village located in Tuscany, in the province of Siena. It is famous for its medieval towers, which have earned it the nickname "Manhattan of the Middle Ages".
The medieval towers: There were once over 70, today 14 remain, making the village unique in the word. They were symbols of power of the noble families.
UNESCO Heritage: The historic center of San Gimignano was declared a World Heritage Site by UNESCO in 1990.
San Gimignano is an unmissable destination for those visiting Tuscany, perfect for immersing yourself in the medieval atmosphere and enjoying breathtaking views.

Available languages

Guide guide

EN IT

Reviews breakdown

Tripadvisor 5.0

4 reviews

5★

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1★

Important information

Infants and small children can ride in a pram or stroller

Public transportation options are available nearby

Specialized infant seats are available

Suitable for all physical fitness levels

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