Skip to main content
Discover
Top Arezzo activities
Explore by category
Culture
Dining Experiences
Cooking Classes
Food Tours
Multi-day Tours
Archaeology Tours
Outdoor Activities
Private Sightseeing Tours
Classes & Workshops
Pizza Making Classes
Day Trips
All categories
Similar categories
Bike Tours
Bus Tours
Car Tours
Classic Car Tours
E-Bike Tours
Mountain Bike Tours
Rentals
Self-guided Tours
Walking Tours
Cruises & Sailing
How to Get Around
Private and Luxury
Popular day Trips from Arezzo
Montepulciano
Siena
San Gimignano
Florence
Top Arezzo landmarks
Top Arezzo landmark tickets
Pienza tickets
Santa Margherita Basilica (Basilica di Santa Margherita) tickets
Prada Outlet tickets
Arezzo Piazza Grande tickets
Chiesa di Santa Maria della Pieve tickets
Arezzo Cathedral tickets
Villa La Ripa tickets
Basilica of San Francesco tickets
Beyond Arezzo
Tours in nearby places
Montepulciano Tours
Chianti Tours
Siena Tours
Perugia Tours
San Gimignano Tours
Florence Tours
Orvieto Tours
Assisi Tours
Montecatini Terme Tours
Livorno Tours
Lucca Tours
Pisa Tours
Explore Tuscany tours
Florence Tours
Siena Tours
Pisa Tours
Livorno Tours
Lucca Tours
San Gimignano Tours
Chianti Tours
Montepulciano Tours
Montecatini Terme Tours
Isola d'Elba Tours
Versilia Tours
Poggibonsi Tours
All popular tours in<br/>Tuscany
Tours in similar places
Florence Tours
Rome Tours
Siena Tours
Venice Tours
Montepulciano Tours
Sorrento Tours
Assisi Tours
Milan Tours
Lucca Tours
Paris Tours
Bologna Tours
San Gimignano Tours
Arezzo trip ideas
Top 15 things to do in ...
Arezzo
Tuscany
Montepulciano
Chianti
Siena
Perugia
San Gimignano
Florence
Orvieto
Assisi
Montecatini Terme
Livorno
Home
Things to do in Italy
Things to do in Tuscany
Things to do in Arezzo
Arezzo Tours
Tours, Sightseeing & Cruises
How to Get Around
Luxury Car Tours
Top Arezzo Luxury Car Tours
Select Dates
Filters
Luxury Car Tours
Private Sightseeing Tours
Food Tours
Bus Tours
Wine Tours
Wine Tastings
Culinary Tours
Day Trips
Full-day Tours
Sightseeing Tours
4 results
Best Seller
Take a break in the countryside with a private tour that includes visits to boutique wineries and a sustainable, family run cheese farm. Enjoy a full day dedicated to wine and cheese, exploring the heart of Tuscany. Drive through the Val d'Orcia, a UNESCO World Heritage Site, and savor some of the region’s finest red wines, including Vino Nobile di Montepulciano and Brunello di Montalcino. Stroll through the medieval squares of Pienza and sample authentic Tuscan cheeses at a historic estate, featuring one of the most breathtaking terraces overlooking the Orcia Valley.
...More
1
2
3
4
5
6
7
4.5
(6)
Private tour Wine and cheese a perfect combinations val 'Orcia
8 to 9 hours
Free Cancellation
from
$550
Price varies by group size
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.
...More
1
2
3
4
5
6
7
5.0
(4)
Private Tour Siena San Gimignano and Chianti from Cortona
8 to 9 hours
Free Cancellation
from
$490
Price varies by group size
Likely to Sell Out
Tuscany is famed for its scenery and gastronomy, but navigating this rustic region isn’t easy—especially for first-time visitors. Enjoy a deluxe introduction to the rolling Tuscan landscape during this full-day tour of Cortona and Montepulciano. A heart Tuscan lunch is included, plus a guided tour of a historic wine cellar and five exclusive wine tastings.
...More
1
2
3
4
5
6
7
39
Operator reviews
Private Art & Wine Tour in Cortona & Montepulciano, with lunch & 2 wine tastings
8 hours
Free Cancellation
from
$311
Price varies by group size
This exclusive private wine tour takes you from Cortona to the heart of the Chianti Classico Black Rooster, an iconic wine area rarely reached from this part of Tuscany. Travel in comfort with a local professional driver and enjoy a personalized journey through one of Tuscany’s most celebrated wine landscapes. The experience includes visits to three carefully selected Chianti Classico DOCG wineries, where you will enjoy guided cellar tours and premium wine tastings. Each winery offers a different perspective on the Black Rooster tradition, allowing you to discover the diversity, history, and craftsmanship behind authentic Chianti Classico wines. A traditional Tuscan lunch is included, perfectly paired with local wines and seasonal products, for a complete and immersive Chianti experience. Designed for travelers seeking authenticity, privacy, and high-quality wine experiences, this tour combines culture, scenery, and exceptional flavors in a relaxed and exclusive setting.
...More
1
2
3
4
5
6
43
Operator reviews
Chianti Classico Black Rooster Private Wine Tour from Cortona
8 to 9 hours
Free Cancellation
from
$562
Price varies by group size
en
44cd8c6a-3a1c-40d4-b014-6fd7a86ed2d0
things_to_do_tag
Not seeing something you are looking for?
See all Arezzo Experiences
More Tours in Arezzo
Things to do near Arezzo
Popular on Viator
Day Trips from Arezzo
Arezzo Best Experiences
Culture
Unique Experiences
Dining Experiences
Cooking Classes
Food Tours
Multi-day Tours
Archaeology Tours
Outdoor Activities
Classes & Workshops
Pizza Making Classes
Nature and Wildlife Tours
Mountain Bike Tours