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Chianti Tours

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Livorno Shore Excursion: Chianti and Tuscany Countryside Private Wine Tour

When your cruise ship docks in Livorno and you have only a single day to see the Tuscan countryside, you’ll need a privately guided, fully …More

Likely to Sell Out
Likely to Sell Out
5.0 (86)

Livorno Shore Excursion: Chianti and Tuscany Countryside Private Wine Tour

When your cruise ship docks in Livorno and you have only a single day to see the Tuscan countryside, you’ll need a privately guided, fully...

9 hours • Free Cancellation
5.0 (86)
from
$209
Private Guided Tour: Siena, San Gimignano and Chianti Day Trip from Florence

Experience for your private group. Come with us for an unforgettable day spent visiting Siena with a professional city guide and the Chianti area accompanied …More

4.9 (22)

Private Guided Tour: Siena, San Gimignano and Chianti Day Trip from Florence

Experience for your private group. Come with us for an unforgettable day spent visiting Siena with a professional city guide and the Chianti area accompanied...

8 hours • Hotel pickup offered • Free Cancellation
4.9 (22)
from
$1,101
Open Top Van!! Half Day in Chianti with Wine Tasting

If you do not have much time but still want to visit the beauties of Chianti and have the opportunity to taste the famous wine …More

5.0 (10)

Open Top Van!! Half Day in Chianti with Wine Tasting

If you do not have much time but still want to visit the beauties of Chianti and have the opportunity to taste the famous wine...

4 to 5 hours • Free Cancellation
5.0 (10)
from
$157
Discover Montalcino through its best productions: Brunello & Saffron!!

Enjoy an unforgettable day: let us guide you through the rolling hills and vineyards to discover the local flavors and scents Montalcino is a land …More

5.0 (3)

Discover Montalcino through its best productions: Brunello & Saffron!!

Enjoy an unforgettable day: let us guide you through the rolling hills and vineyards to discover the local flavors and scents Montalcino is a land...

3 hours 30 minutes
5.0 (3)
from
$243
Discovering Chianti, e-bike tour - daily experience

Our tour is a captivating blend of adventure, art, history, natural beauty, and gastronomic delights. Our dedication and meticulous attention to detail set us apart. …More

5.0 (14)

Discovering Chianti, e-bike tour - daily experience

Our tour is a captivating blend of adventure, art, history, natural beauty, and gastronomic delights. Our dedication and meticulous attention to detail set us apart....

6 hours • Free Cancellation
5.0 (14)
from
$325
Luxury Brunello Tour

When we say "exclusive" we mean it. In this tour we have selected for you, unique experiences in each of the 2 wineries you are …More

5.0 (1)

Luxury Brunello Tour

When we say "exclusive" we mean it. In this tour we have selected for you, unique experiences in each of the 2 wineries you are...

8 hours • Hotel pickup offered • Free Cancellation
5.0 (1)
from
$462
Brunello E-Bike Tour

Half day e-bike tour in the land of Brunello starting from the medieval town of Montalcino. The e-bike tour is set on the southern part …More

5.0 (8)

Brunello E-Bike Tour

Half day e-bike tour in the land of Brunello starting from the medieval town of Montalcino. The e-bike tour is set on the southern part...

5 to 6 hours • Free Cancellation
5.0 (8)
from
$220
MONTALCINO Private E-Bike & Brunello Winery Experience

Ride through the rolling hills of Montalcino on a private e-bike experience for travelers seeking authenticity, exceptional wines, and a deeper connection with Tuscany.Set in …More

5.0 (7)

MONTALCINO Private E-Bike & Brunello Winery Experience

Ride through the rolling hills of Montalcino on a private e-bike experience for travelers seeking authenticity, exceptional wines, and a deeper connection with Tuscany.Set in...

3 to 5 hours • Free Cancellation
5.0 (7)
from
$404
Montepulciano Pienza Montalcino Tour from Siena

Today we will drive you to the famous Orcia Valley, one of the most beautiful area in Tuscany. Here we will visit 3 stunning medieval …More

5.0 (5)

Montepulciano Pienza Montalcino Tour from Siena

Today we will drive you to the famous Orcia Valley, one of the most beautiful area in Tuscany. Here we will visit 3 stunning medieval...

8 to 9 hours • Hotel pickup offered • Free Cancellation
5.0 (5)
from
$1,145
Private Chianti Wine Tour with Transfers from Florence

Escape Florence for the rolling hills of Chianti on this private wine tour with transfers included. Travel in comfort by air-conditioned vehicle as you make …More

5.0 (5)

Private Chianti Wine Tour with Transfers from Florence

Escape Florence for the rolling hills of Chianti on this private wine tour with transfers included. Travel in comfort by air-conditioned vehicle as you make...

6 hours • Free Cancellation
5.0 (5)
from
$452
Meet the king of the territory: Brunello di Montalcino

Original full day tour that will lead you into the most charming wine cellars which produce the king of Italian wines: Brunello di Montalcino. An experience among …More

5.0 (2)

Meet the king of the territory: Brunello di Montalcino

Original full day tour that will lead you into the most charming wine cellars which produce the king of Italian wines: Brunello di Montalcino. An experience among...

7 hours
5.0 (2)
from
$405
Montalcino wine tour

A unique way to discover the colours, the landscapes, to taste the flavours of this land, come and meet the producers, enojoy the wines, and …More

4.2 (6)

Montalcino wine tour

A unique way to discover the colours, the landscapes, to taste the flavours of this land, come and meet the producers, enojoy the wines, and...

9 hours
4.2 (6)
from
$406
Chianti: eno-excursion through the vineyards

Excursion in the heart of Chianti, among the rolling hills covered with vineyards, olive groves and dotted with villages suspended in time, we will also …More

5.0 (1)

Chianti: eno-excursion through the vineyards

Excursion in the heart of Chianti, among the rolling hills covered with vineyards, olive groves and dotted with villages suspended in time, we will also...

3 to 5 hours • Free Cancellation
5.0 (1)
from
$70

Frequently Asked Questions

These answers are based on answers previously given to Cool Destinations customers' questions.

Recent tour reviews
Special Experience
New York City
MONTALCINO Private E-Bike & Brunello Winery Experience
kimpV7805AP, Sep 2026
Special Experience
We loved our day with Roberto! Our bike ride was lovely and safe. Our pick up was smooth. Our lunch was delicious and the winery couldn’t have been kinder! This was a private one of a kind experience that was as peaceful as it was entertaining!
Read more
Great time, great wine!
New York City
Livorno Shore Excursion: Chianti and Tuscany Countryside Private Wine Tour
175gavina, Sep 2026
Great time, great wine!
Leo was excellent! His knowledge of the area and his driving are top notch. I had such a fantastic time and learned so much about wine and the area!
Read more
Great trip in gorgeous...
New York City
Open Top Van!! Half Day in Chianti with Wine Tasting
Danute_K, Sep 2026
Great trip in gorgeous...
Great trip in gorgeous weather! It’s not a half day trip… by the way. But we loved it. The first winery was very remote and long when it did not need be and too short of a time in Greve!!!! Driver was great!
Read more
Unforgettable experience
New York City
Private Chianti Wine Tour with Transfers from Florence
stellarH7898FA, Aug 2026
Unforgettable experience
An unforgettable experience in the heart of Chianti! Everything was perfectly organized, with breathtaking views, beautiful vineyards and charming Tuscan scenery. The highlight was definitely the sunset, with incredible colors and a magical atmosphere. The wine tasting and local products were excellent. A truly authentic and romantic experience. Highly recommended!
Read more
Excellent experience, I recommend it to everyone!
New York City
Private Chianti Wine Tour with Transfers from Florence
422jetmiras, Aug 2026
Excellent experience, I recommend it to everyone!
Excellent experience!! I sincerely recommend it.
Read more
Delicious wine, Leo is the GOAT
New York City
Livorno Shore Excursion: Chianti and Tuscany Countryside Private Wine Tour
huntermR770DG, Aug 2026
Delicious wine, Leo is the GOAT
We had a fantastic time on this tour! Leo, our guide, was friendly, informative, and answered all our questions from us as novice wine tasters. The wine was delicious, I would highly recommend this tour.
Read more
Discovery of the Val d’Orcia by ebike
New York City
MONTALCINO Private E-Bike & Brunello Winery Experience
Adrien2513, Aug 2026
Discovery of the Val d’Orcia by ebike
We had a lot of fun doing this family outing in the hills of the Tuscan countryside. The personalized tour organized by Roberto was perfect. Passionate about his work and the region, he gave us a lot of historical information and knew how to spark our children's interest. We were also delighted by the welcome we received at the Colsereno wine resort for dinner and the winery tour, Authentic experience, we recommend it 200%.
Read more
Unforgettable trip!
New York City
Private Guided Tour: Siena, San Gimignano and Chianti Day Trip from Florence
Wander15577008171, Jun 2026
Unforgettable trip!
These towns can’t be missed. We had the pleasure of spending the day with Giacomo. His strong English skills allowed for great conversation. He is deeply knowledgeable about the history of Italy and Tuscany. He was kind enough to make a small detour to the American cemetery outside of Florence, and a small monastery near San Gimignano that were deeply moving.Lunch was at a beautiful winery, Terre Di Sovernaja, overlooking the Tuscan hills. The food was simple and so delicious, complimented perfectly with their wine.We explored San Gimignano on our own and Giacomo guided us through Siena with a stop for a quick espresso at an off the path cafe. His warmth and deep knowledge made for a memorable experience overall.
Read more
Recommend it to anyone!
New York City
Open Top Van!! Half Day in Chianti with Wine Tasting
sarasK4843QI, May 2026
Recommend it to anyone!
Loved getting out of the city for the fresh air. The special stop at the War Memorial made it extra special. Very knowledgeable and easy to communicate with. We felt very safe and comfortable.
Read more
Rachel & Meg had a great day with Camilla!
New York City
Luxury Brunello Tour
megancW4069UI, Apr 2026
Rachel & Meg had a great day with Camilla!
Camilla was an amazing and knowledgeable guide! She was a great driver and educated us on everything from wine to the history of the region and was so fun and personable. We really enjoyed her fun and warm personality and were very impressed that she spoke so many different languages! The wines and lunch were incredible and we had such a special day. If you want to enjoy montalcino wine without stress, book with Camilla and you are in for a relaxing and enjoyable day! XX
Read more
Family ride in Tuscany
New York City
Brunello E-Bike Tour
811karam, Jul 2025
Family ride in Tuscany
We did a 60 km ride through Tuscany near Montalcino. We had an amazing day with our guide. The bikes were in fantastic shape and would do it again in a heartbeat. Thank you so much!
Read more
Wonderful day!!
New York City
Discover Montalcino through its best productions: Brunello & Saffron!!
Katherine_D, Jun 2025
Wonderful day!!
We thoroughly enjoyed this experience. We visited a family-owned winery and even met the owner, who made the appetizers for us. It was a very special experience and the wines were remarkable. We also loved our visit to the saffron farm. The honey and saffron cream were our favorites there. A wonderful experience from start to finish, with knowledgeable and friendly guides. I highly recommend!
Read more
The only driver service I book as an expat in Italy for 2 decades!
New York City
Private Guided Tour: Siena, San Gimignano and Chianti Day Trip from Florence
GeneAndDeanWeen, May 2025
The only driver service I book as an expat in Italy for 2 decades!
I have lived in Italy for nearly 20 years and whenever I have friends or family visiting, I book Massimo as our driver. Some of my most memorable experiences in Italy have been out on an excursion with Chianti Drivers! This April, Massimo picked us up in Florence and took us to San Gimignano and Monteriggioni for time to explore on our own. Next, we headed to an exquisite winery for lunch and a cellar tour, before heading to Siena. Massimo is always exceedingly professional, punctual and polite. I cannot recommend this company enough!
Read more
Beautiful scenery
New York City
Discovering Chianti, e-bike tour – daily experience
M3247DKcarolh, Oct 2024
Beautiful scenery
The scenery was amazing! We LOVED it! Alberto made the bike tour so interesting. The bikes were so easy to use. The Abbey is a hidden gem. The lunch was perfect with the wine tasting. We had to do a lot of luggage shuffling to get the 5 bottles of olive oil and wine packed. If you know,…you know!
Read more
Fantastic tour, tastings, and guide
New York City
Montepulciano Pienza Montalcino Tour from Siena
P4526WYkellym, Oct 2024
Fantastic tour, tastings, and guide
Absolutely fantastic way to spend the day exploring smaller towns in Tuscany made possible by Francesco’s friendly demeanor, historical knowledge, and impeccable service. Not only did we enjoy the medieval castles, churches, and walkways but also the rolling hills of Tuscany. Francesco arranged for a fantastic wine tasting and tour as well as special lunch with tour of ancient shields. Francesco also made helped us make reservations for upcoming visits we were making on our own. He truly went and beyond to make our stay enjoyable and easy. He is a great ambassador for Tuscany!
Read more
Phenomenal day in Tuscany with wine and olive oil tastings, shopping, exploring, and - wonderful guide!
New York City
Montepulciano Pienza Montalcino Tour from Siena
151helenh, Oct 2024
Phenomenal day in Tuscany with wine and olive oil tastings, shopping, exploring, and - wonderful guide!
We had an amazing day visiting these three cities and touring the Tuscany area. Francesco also arranged a wine tour and tasting at a beautiful winery, Paradiso di Cacuci, which also included olive oil tasting. We then had a wonderful lunch outside Montalpulcino and went into the city to shop. Montalcino and Pienza were also wonderful cities to visit. Francesco provided great historical and informational insights on the area and cities and gave us wonderful recommendations to explore. It was an exceptional experience and o highly recommend booking Francesco for your visit. He also gave us great recommendations for lunch in a town we were visiting the next day on our own as well as for dinner in Florence for later in the week and arranged reservations for us at each restaurant. He has a wealth of information and is willing to share it.
Read more
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