Headout logo. Link to home.
Help

4.4(4.7K ratings)Rated 4.4 out of 5.0 from 4727 ratings.

Florence To Chianti Tours

The verdant Chianti Classico region is teeming with vineyards and olive oil mills. Explore Chianti and other picturesque places like San Gimignano and Monteriggioni. Go on a wine tour and enjoy the countryside with our Florence to Chianti tours.
Florence To Chianti Tours
Transportation from Florence during Chianti Wine Tour
Tourist enjoying wine tasting at Chianti Winery
Exterior view of the winery in Chianti
A tour escort waiting to meet tourist at the meeting point
Interior view of the wine storage facilities in Chianti
A tour escort giving information to tourists
View of wine and vineyard during Chianti Wine Tasting Tour
Free Cancellation
Instant Confirmation
5 hours
2 more
  • Depart Florence on a cozy AC bus for your wine-tasting journey in Chianti, exploring the renowned land of the black rooster!

  • Enjoy tastings at two distinct Chianti Classico vineyards and savor other local delights, including extra virgin olive oil.

  • Discover the wine production process through tours of historic cellars and vineyards in your preferred language.

  • Immerse yourself in the allure of the Tuscan countryside, where rolling hills, vineyards, and olive groves serenade you along the 'Via Chiantigiana'.

More details

  • Depart Florence on a cozy AC bus for your wine-tasting journey in Chianti, exploring the renowned land of the black rooster!

  • Enjoy tastings at two distinct Chianti Classico vineyards and savor other local delights, including extra virgin olive oil.

  • Discover the wine production process through tours of historic cellars and vineyards in your preferred language.

  • Immerse yourself in the allure of the Tuscan countryside, where rolling hills, vineyards, and olive groves serenade you along the 'Via Chiantigiana'.

from
€49
Facade of Siena Cathedral
Group of tourists enjoying a wine tasting session on a Chianti Half Day Afternoon Tour in a Tuscan vineyard, Italy
Scenic view of Chianti vineyards during a half day afternoon tour
Guests enjoying wine tasting in Chianti
Guests enjoying dinner during Chianti Half Day Wine Tasting Tour
Mont St. Michel Abbey view with tourists exploring the historic site on a full-day tour from Paris.
Free Cancellation
Instant Confirmation
7 hours
3 more
  • Set off from Florence along the 'Via Chiantigiana' on a spacious AC bus, regaled by expert live commentary in English or Spanish.

  • Get ample free time at your first stop, Siena, and explore the central Plaza del Campo or the interesting Santa Maria della Scala museum.

  • Make your way to a rustic vinery in the heart of Chianti, where traditional pasta and other seasonal dishes are accompanied by the perfect wines!

  • Did you know? The republics of Florence and Siena fought over Chianti in the Middle Ages – and divided the territory using roosters and knights!

More details

  • Set off from Florence along the 'Via Chiantigiana' on a spacious AC bus, regaled by expert live commentary in English or Spanish.

  • Get ample free time at your first stop, Siena, and explore the central Plaza del Campo or the interesting Santa Maria della Scala museum.

  • Make your way to a rustic vinery in the heart of Chianti, where traditional pasta and other seasonal dishes are accompanied by the perfect wines!

  • Did you know? The republics of Florence and Siena fought over Chianti in the Middle Ages – and divided the territory using roosters and knights!

from
€79
Exterior view of the Piazza del Campo in Siena
San Gimignano skyline with medieval towers during Siena, San Gimignano, Monteriggioni tour from Florence.
Exterior view of the winery in Chianti
View of wine and vineyard during Chianti Wine Tasting Tour
Siena cathedral, San Gimignano towers, Monteriggioni walls, Chianti vineyards on Florence tour.
A tour escort waiting to meet tourist at the meeting point
Visitors on a bus transfer to Chianti from Florence
Free Cancellation
Instant Confirmation
11 hours30 minutes
3 more
  • Travel in style with round-trip transfers from Florence by GT coach, complete with seamless multilingual support.

  • Experience Siena’s rich history on a guided tour, from the stunning Palazzo Pubblico to the iconic Torre del Mangia in the lively Piazza del Campo.

  • Wander amidst the medieval towers of San Gimignano, a UNESCO World Heritage Site, and let your curiosity lead the way through its historic streets.

  • Delight in the world of Chianti as you stroll through a local estate, uncovering the secrets of winemaking while enjoying tastings and local bites.

More details

  • Travel in style with round-trip transfers from Florence by GT coach, complete with seamless multilingual support.

  • Experience Siena’s rich history on a guided tour, from the stunning Palazzo Pubblico to the iconic Torre del Mangia in the lively Piazza del Campo.

  • Wander amidst the medieval towers of San Gimignano, a UNESCO World Heritage Site, and let your curiosity lead the way through its historic streets.

  • Delight in the world of Chianti as you stroll through a local estate, uncovering the secrets of winemaking while enjoying tastings and local bites.

from
€75
Aerial view of San Gimignano
Exterior view of the Sienna Cathedral
Aerial view of the Walls of Monteriggioni
Tourists having lunch in Chianti
Aerial view of the Chianti winery
Mont St. Michel Abbey view with tourists exploring the historic site on a full-day tour from Paris.
San Gimignano towers, Siena cathedral, Monteriggioni walls, Chianti vineyards, day trip lunch, wine tasting.
Free Cancellation
Instant Confirmation
9 hours
4 more
  • Traverse Siena at your own pace or join a guided tour, discovering the central square and, if selected, the famed Siena Cathedral.

  • Visit a charming Chianti winery, where you'll enjoy a delectable 3-course lunch complemented by a range of exquisite wines.

  • Wander through the hilltop town of San Gimignano, admiring its towering structures and uncovering beautiful frescoes.

  • Between April and October, the tour may include a stop at the walled commune of Monteriggioni.

  • Fun fact: San Gimignano was once known as the 'Manhattan of the Middle Ages' due to its remarkably modern-looking urban skyline!

More details

  • Traverse Siena at your own pace or join a guided tour, discovering the central square and, if selected, the famed Siena Cathedral.

  • Visit a charming Chianti winery, where you'll enjoy a delectable 3-course lunch complemented by a range of exquisite wines.

  • Wander through the hilltop town of San Gimignano, admiring its towering structures and uncovering beautiful frescoes.

  • Between April and October, the tour may include a stop at the walled commune of Monteriggioni.

  • Fun fact: San Gimignano was once known as the 'Manhattan of the Middle Ages' due to its remarkably modern-looking urban skyline!

from
€79
Group of tourists enjoying a wine tasting session on a Chianti Half Day Afternoon Tour in a Tuscan vineyard, Italy
View of the San Gimignano
Tour group exploring Pisa from La Spezia, with optional visit to the Leaning Tower and the jewel of the Cinque Terre
Facade of Siena Cathedral
Transportation from Florence during Chianti Wine Tour
Aerial view of the Chianti winery
Guests having lunch in Tuscany
Lunch and wine tasting during Day Tour of Siena, San Gimignano, Chianti & Pisa
View of the streets in a Tuscan village
Free Cancellation
Instant Confirmation
12 hours
4 more
  • Begin in Pisa with a visit to the Square of Miracles, where you’ll have plenty of time to pose with the iconic Leaning Tower.

  • Enjoy a satisfying lunch with top-notch wines in San Gimignano, then explore its historic 13th-century walls and stone towers.

  • Discover the allure of Siena’s medieval squares, with the option to enrich your experience by adding a guided tour of the city and its cathedral.

  • Experience a spacious ride to and from Florence with dedicated multilingual assistance on board.

  • Did you know? San Gimignano is the 'World Capital of Gelato', and has several renowned gelaterias offering a variety of delicious flavors.

More details

  • Begin in Pisa with a visit to the Square of Miracles, where you’ll have plenty of time to pose with the iconic Leaning Tower.

  • Enjoy a satisfying lunch with top-notch wines in San Gimignano, then explore its historic 13th-century walls and stone towers.

  • Discover the allure of Siena’s medieval squares, with the option to enrich your experience by adding a guided tour of the city and its cathedral.

  • Experience a spacious ride to and from Florence with dedicated multilingual assistance on board.

  • Did you know? San Gimignano is the 'World Capital of Gelato', and has several renowned gelaterias offering a variety of delicious flavors.

from
€78
Guests exploring wine celler in Chianti
A female guide giving information to guests during Guided Immersive Wine & Olive Oil Experience in Chianti
A male guide giving information to guests during Guided Immersive Wine & Olive Oil Experience in Chianti
Guests having lunch in Tuscany
Guests having lunch in Tuscany
Olive oil tasting setup during a guided immersive wine and olive oil experience in Chianti.
Chianti vineyard tour with wine and olive oil tasting experience.
Guests having lunch in Tuscany
Minivan transfer from Tokyo during visit to Harry Potter Studios
Free Cancellation
Instant Confirmation
7 hours
4 more
  • Relax on a luxury AC vehicle from Florence to Chianti as you learn about the fascinating ‘land of the black rooster' on this one-of-a-kind tour.

  • Enjoy samples at an olive oil mill and three wineries, exploring every step of Italy’s precious gastronomy from vineyard to cellar.

  • Conclude with a traditional Tuscan lunch, savoring the flavors after discovering the diverse estates of the village.

More details

  • Relax on a luxury AC vehicle from Florence to Chianti as you learn about the fascinating ‘land of the black rooster' on this one-of-a-kind tour.

  • Enjoy samples at an olive oil mill and three wineries, exploring every step of Italy’s precious gastronomy from vineyard to cellar.

  • Conclude with a traditional Tuscan lunch, savoring the flavors after discovering the diverse estates of the village.

from
€149
Pouring wine
Chianti vineyards with wine barrels, part of guided tour including two tastings in Florence, Italy.
Chianti wine region vineyard with tour group enjoying wine tasting experience in Florence, Italy.
Chianti wine region vineyard with guided tour group tasting wine in Florence, Italy.
Chianti vineyards with wine barrels, part of guided tour featuring two wine tastings in Florence, Italy.
Chianti vineyards with wine barrels, part of a guided tour featuring two wine tastings in Florence, Italy.
Chianti vineyards with wine barrels, part of a guided tour featuring two wine tastings in Florence, Italy.
Chianti vineyards with wine barrels, part of a guided tour featuring two wine tastings in Florence, Italy.
Free Cancellation
Instant Confirmation
5 hours
2 more
  • Sample high-level Chianti wines and regional snacks at two wineries amidst the Tuscan hills as you explore the rolling landscapes!

  • Unravel the secrets of Chianti wines with a personalized tour of the vineyards and the cellars with a local escort and meet a professional winemaker.

  • Capture memorable photographs of the idyllic scenery and purchase local wine, balsamic vinegar, and olive oil at exclusive prices.

  • Travel comfortably on a fully-fitted GT coach with roundtrip transportation from Florence and choose the guided tour in English or Spanish.

  • Fun Fact: The Chianti wine region has been producing wines for thousands of years, with the first recorded evidence dating back to the 13th century.

More details

  • Sample high-level Chianti wines and regional snacks at two wineries amidst the Tuscan hills as you explore the rolling landscapes!

  • Unravel the secrets of Chianti wines with a personalized tour of the vineyards and the cellars with a local escort and meet a professional winemaker.

  • Capture memorable photographs of the idyllic scenery and purchase local wine, balsamic vinegar, and olive oil at exclusive prices.

  • Travel comfortably on a fully-fitted GT coach with roundtrip transportation from Florence and choose the guided tour in English or Spanish.

  • Fun Fact: The Chianti wine region has been producing wines for thousands of years, with the first recorded evidence dating back to the 13th century.

from
€55
Chianti Hills vineyard with wine tasting setup in Florence, Italy.
Chianti Hills vineyard with wine tasting experience in Florence, Italy.
Chianti Hills vineyard with wine tasting setup, Florence, Italy.
Chianti Hills vineyard with wine tasting setup in Florence, Italy.
Chianti Hills vineyard with wine tasting setup, Florence, Italy.
Wine tasting tour group enjoying a sunny day in the lush vineyards of the Chianti Hills, Italy
Chianti Hills vineyard with wine tasting setup in Florence, Italy.
Free Cancellation
Instant Confirmation
6 hours
3 more
  • Visit two old vineyards in the Chianti Hills and try a variety of wines from the area while taking in the beautiful scenery of Tuscany on this tour.

  • Explore a beautiful and charming town at your own pace and buy some of the best wines, olive oil, and other specialties from the area.

  • Sample up to six wines while enjoying the exotic Chianti hills in the background.

  • You can choose to take the tour in English, Spanish, French, Italian, German, or Portuguese.

  • Fun fact: Chianti wine is traditionally served in a straw basket known as a "fiasco" which means "bottle" in Italian, traditionally used to hold the wine because the thick, uneven glass of the bottles helped to protect the wine from breaking and sunlight during transport.

More details

  • Visit two old vineyards in the Chianti Hills and try a variety of wines from the area while taking in the beautiful scenery of Tuscany on this tour.

  • Explore a beautiful and charming town at your own pace and buy some of the best wines, olive oil, and other specialties from the area.

  • Sample up to six wines while enjoying the exotic Chianti hills in the background.

  • You can choose to take the tour in English, Spanish, French, Italian, German, or Portuguese.

  • Fun fact: Chianti wine is traditionally served in a straw basket known as a "fiasco" which means "bottle" in Italian, traditionally used to hold the wine because the thick, uneven glass of the bottles helped to protect the wine from breaking and sunlight during transport.

from
€49

Browse by themes

Millions love heading out with us

John Zumwalde

John

5/5
We had a very great tour. Our guide Assia was excellent! She was informative and kept our group moving. Highly recommend.
Guided tour of Siena, San Gimignano & Monteriggioni with Wine Tasting in Chianti
Mária Šoltésová

Mária

5/5
It was a great experience and we enjoyed it a lot. We visited 3 towns, had a tasty lunch and a wine degustation - all with a very nice tour guide. I recommend this trip a lot.
Guided tour of Siena, San Gimignano & Monteriggioni with Wine Tasting in Chianti
Devanshu Malhotra
IN

Devanshu

5/5
India
It was excellent. Really enjoyed. Two wineries that they selected was just perfect. You'll find perfect spots for some picturesque pictures
From Florence: Siena and Chianti Day Trip with Dinner & Wine Tasting
CLAUDIO PACHECO DE MORAIS
BR

Claudio

4/5
Brazil
Despite choosing the Spanish tour, the group was mixed in English, Spanish and Italian. However, the guide who accompanied the group gave explanations in all three languages. Only in the 2 wineries we visited was the language only in English or Italian. The 2 visits to the wineries were good, with a small tasting of bread with olive oil and 3 wines in each (starter wines).
View original review in Portuguese
From Florence: Chianti Wine Tasting Tour
Andrew Smith-West
GB

Andrew

5/5
United Kingdom
The visit to Siena, San Gimignano & the Chianti lunch & wine tasting were all very good. The tour leader was excellent.
From Florence: Siena, San Gimignano & Chianti Day Trip with Lunch & Wine Tasting
Kaminthia O'Neill
AU

Kaminthia

5/5
Australia
Wonderful trip with great guide and very informative!! We had lots of time to explore on our own. Great food and amazing g wine tasting! Tour company were great and the entire day ran very well Would highly recommend this tour
From Florence: Siena, San Gimignano & Chianti Day Trip with Lunch & Wine Tasting
Juan Felipe Cadena Gonzalez
US

Juan

4/5
United States
The tour was very nice. My mother and I really enjoyed all the places we visited. Lunch in San Gimignano was delicious, accompanied by local Tuscan products, which made the experience even more special. For those who prefer to tour the towns without any rush, we suggest doing it on your own. Finally, we would like to thank immensely the help offered by the guide Alexandra who very kindly helped us find a place to leave our luggage in Siena as we were not ending the tour in Florence as scheduled, but were heading to another destination. Without his help we would not have known Siena. Excellent as a professional and as a person.
View original review in Spanish
From Florence: Pisa, San Gimignano, Siena & Chianti Day Trip with Lunch & Wine Tasting
Prachi Jain
IN

Prachi

5/5
India
Hi, My experience with Headout team and the guide was suoer amazing, I think on our own we wouldn't have ever visited so many places in one day, but due to this trip we could visit so much and the guide was also very informative. I speacially love the wine tasting experience. Wish we would have got more time everywhere but it was a little hectic but worth visting ..I just loved it.
From Florence: Pisa, San Gimignano, Siena & Chianti Day Trip with Lunch & Wine Tasting

World at your tap.

Get the Headout app to get tickets on your phone and access app-only deals. Talk about win-win.
iphone

We've served 32 million+ guests and we are here for you

32 million+

Happy customers across 10,000+ experiences

4.4/5

28,000+ verified reviews with 90% excellent score

In the media

Featured and recommended by the best brands

24 x 7 help center

Have a question? Live chat with local experts anywhere, anytime