"Ramble Through The Rolling Hills Of Chianti" with lunch and 2 wine tastings

Arezzo , Italy

"Ramble Through The Rolling Hills Of Chianti" with lunch and 2 wine tastings

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About this experience

Spend an unforgettable day in the heart of the Chianti Hills, surrounded by cypress-lined roads, vineyards, sunflowers, and charming medieval villages. Discover the enchanting village of Castellina in Chianti, savor homemade pasta, and indulge in the finest Chianti wines at two authentic Tuscan wineries.

ITINERARY:
• Morning pickup at your hotel, B&B, or private flat by our driver.
• Enjoy a scenic drive through the rolling Chianti hills, with olive groves, cypress trees, and endless vineyards.
• Explore the medieval village of Castellina in Chianti and stroll through its historic center.
• For lunch, visit a traditional Tuscan farm, discover the secrets of wine production, and enjoy a meal paired with 5 local wine tastings.
• On the way back, stop at a charming local winery to savor wine made the old-fashioned way.

What to expect: A day of beauty, flavors, and the timeless magic of Tuscany!

Available options

"Ramble Through The Rolling Hills Of Chianti" with lunch and 2 wine tastings

Pickup included

What's included

Local expert driver

Private transportation

3 course Lunch Menu in a tipical Wine - Farm with Bruschettas, home made pasta, cold cuts, Pecorino Cheese, extravergine olive oil, truffle oil and more

Bottled water

Air-conditioned vehicle

2 wine tastings in 2 different farm wineries - About 12 glasses (Chianti DOCG, Chianti Riserva, Vernaccia and Super Tuscan)

Detailed itinerary

Our driver will pick you up and guide you along the Via Chiantigiana, a picturesque route winding through the Tuscan countryside from the Arezzo area. This scenic road is lined with rolling vineyards, olive groves, and iconic cypress trees, showcasing the timeless beauty of Chianti. As you travel, you’ll pass medieval villages, stone farmhouses, and historic wineries, immersed in a landscape that feels like a living painting. The Via Chiantigiana offers a perfect glimpse into Tuscany’s rich wine culture and serene rural charm.

After an hour, we will arrive in Castellina in Chianti, a charming town with a rich medieval atmosphere. Stroll through its historic center, where artisan shops and traditional wine and cheese boutiques line the streets. Once at the center of battles between Florence and Siena, Castellina offers fascinating history, including the underground vaulted passageways and the medieval fortress, now home to a museum.

Enjoy breathtaking panoramas as you travel along the scenic country roads of Castellina. The landscape is a feast for the senses, with rolling wheat fields, lush vineyards, and cypress-lined curves filling the air with the unmistakable aromas of the Tuscan countryside.

For lunch, we will move to a charming Tuscan farm, where you’ll enjoy an authentic Italian experience surrounded by vineyards and rolling hills. Discover the secrets of Tuscan wine-making and the perfect pairings of food and wine.

You’ll indulge in a delicious 3-course meal featuring:
A selection of bruschettas, cold cuts (salami, prosciutto), and pecorino cheeses
A plate of homemade pasta with traditional Tuscan sauces
The experience includes a guided tasting of 6 exceptional wines, starting with crisp white wines, moving through prestigious Chianti DOCG and Chianti Riserva reds, and finishing with rich and bold Super Tuscans.
To complete the meal, savor tastings of extra virgin olive oil and aged balsamic vinegar, enhancing the authentic flavors of Tuscany.

The final stop will be at a second Chianti winery, such as Lornano or Guidi Winery, a charming family-run estate in the heart of Chianti. Here, wine has been crafted for generations using traditional methods, resulting in limited yet exceptional bottles with a unique flavor.

Enjoy a special wine tasting experience, savoring the rich aromas and flavors of their carefully produced wines.

After this delightful stop, we’ll return to your location—whether it’s your hotel, private flat, or B&B—concluding a perfect day in Tuscany.

What's not included

Everything not found under the heading inclusions is excluded

Available languages

Guide guide

Important information

Specialized infant seats are available

Suitable for all physical fitness levels

Public transportation options are available nearby

Infants and small children can ride in a pram or stroller

All areas and surfaces are wheelchair accessible

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