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#4 out of 29 in Florence

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.

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Florence To Chianti Tours
Dirt road leading to a villa surrounded by cypress trees in Chianti, Tuscany.
Tourists enjoying wine tasting in a Chianti vineyard at sunset.
Vineyards and olive groves in Chianti region, Tuscany, Italy, viewed during a wine tour from Florence.
Visitors walking through a Chianti vineyard with grapevines and a basket of grapes.
Vineyards and cypress trees in the Chianti region landscape, Tuscany, Italy.
Chianti winery tasting room with wooden barrels and set dining tables.
Hand holding a glass of rosé wine in a Chianti vineyard during e-bike tour.
Free cancellation
Instant confirmation
5 hr
1 more
  • Depart Florence on a cozy AC bus for a flavorful journey through Chianti, the 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 a flavorful journey through Chianti, the 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
€45
Siena Cathedral facade with visitors in Piazza del Duomo, Italy.
Santa Maria della Scala museum entrance in Siena, Italy, showcasing historic architecture.
view from AC bus traveling through Via Chiantigiana, Tuscany, with scenic vineyards and rolling hills in the background.
Chianti vineyard landscape during wine tasting tour in Tuscany, Italy.
Vineyard landscape in Chianti, Italy with rows of grapevines and rolling hills.
Group toasting with wine glasses at a vineyard in Tuscany, Italy.
Siena cityscape with historic buildings and lush greenery during Chianti wine tour.
Rolling hills and vineyards in the Tuscan landscape, Italy.
Rows of grapevines in a Tuscany vineyard with rolling hills in the background.
Passengers seated inside a tour bus traveling from Paris to Mont St. Michel's Abbey.
Free cancellation
Instant confirmation
7 hr
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.

  • Head to a rustic vineyard in the heart of Chianti, where traditional pasta and seasonal fare are perfectly paired with locally crafted pours that elevate every bite.

  • Savor a delicious Tuscan dinner made with the finest regional ingredients.

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.

  • Head to a rustic vineyard in the heart of Chianti, where traditional pasta and seasonal fare are perfectly paired with locally crafted pours that elevate every bite.

  • Savor a delicious Tuscan dinner made with the finest regional ingredients.

from €79
€67.15

15% off

Chianti Hills vineyard tour with wine tasting near 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 in Chianti Hills vineyard, Florence, with scenic view of Radda in Chianti.
Chianti Hills vineyard with wine tasting setup in Florence, Italy.
Free cancellation
Instant confirmation
6 hr
2 more
  • Discover the flavors and charm of the Chianti Hills with visits to two scenic countryside estates and leisurely time in a historic Tuscan town.

  • Wander through sun-kissed vineyards and age-old cellars, where you’ll sample regional pours paired with local specialties against a stunning rural backdrop.

  • Stroll through a quaint hilltop town at your own pace and pick up locally made olive oil, artisanal goods, and bottled treats to take home.

  • Experience the rolling landscapes of Chianti with up to six curated tastings at family-run estates nestled among the hills.

  • Choose your language for the tour—available in English, Spanish, French, Italian, German, and Portuguese.

  • Fun fact: Traditional Chianti was once sold in straw-covered flasks called fiaschi, designed to protect its contents on bumpy country roads.

More details

  • Discover the flavors and charm of the Chianti Hills with visits to two scenic countryside estates and leisurely time in a historic Tuscan town.

  • Wander through sun-kissed vineyards and age-old cellars, where you’ll sample regional pours paired with local specialties against a stunning rural backdrop.

  • Stroll through a quaint hilltop town at your own pace and pick up locally made olive oil, artisanal goods, and bottled treats to take home.

  • Experience the rolling landscapes of Chianti with up to six curated tastings at family-run estates nestled among the hills.

  • Choose your language for the tour—available in English, Spanish, French, Italian, German, and Portuguese.

  • Fun fact: Traditional Chianti was once sold in straw-covered flasks called fiaschi, designed to protect its contents on bumpy country roads.

from
€49
Piazza del Campo in Siena with Torre del Mangia and historic buildings.
Streets of San Gimignano with medieval towers and cobblestone paths in Tuscany, Italy.
Vineyards and olive groves in Chianti region, Tuscany, Italy, viewed during a wine tour from Florence.
Hand holding a glass of rosé wine in a Chianti vineyard during e-bike tour.
Siena cathedral, San Gimignano towers, Monteriggioni walls, Chianti vineyards on Florence tour.
A tour escort waiting to meet tourist at the meeting point
Bus transfer from Tromso to Skjervoy with scenic Arctic landscapes in Norway.
Free cancellation
Instant confirmation
11 hr 30 min
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 wine making. Cap your experience with a hearty 3-course Tuscan lunch.

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 wine making. Cap your experience with a hearty 3-course Tuscan lunch.

from
€89
Aerial view of San Gimignano with medieval towers and surrounding countryside.
Siena Cathedral with tourists in the square, part of San Gimignano, Siena, Monteriggioni, Chianti day trip.
Group walking through vineyard on Siena, San Gimignano, and Chianti day trip.
Visitors at the steps of a historic church in San Gimignano, Italy.
Wine being poured into a glass during a Chianti tasting on a Florence day trip.
Tourists taking a selfie in front of historic architecture in San Gimignano, Italy.
Aerial view of Monteriggioni's medieval walls and surrounding Tuscan landscape.
Aerial view of Chianti winery with vineyards and Tuscan landscape.
Passengers seated inside a tour bus traveling from Paris to Mont St. Michel's Abbey.
Free cancellation
Instant confirmation
9 hr
3 more
  • Relax on an AC coach from Florence as you explore Siena, San Gimignano, and Chianti—enjoy free time and a winery lunch with local craft tastings.

  • Stop at Siena and allow it to charm you with its Gothic elegance, narrow winding lanes, and the stunning shell-shaped Piazza del Campo. It’s small enough to explore in a few hours, yet packed with character.

  • 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.

More details

  • Relax on an AC coach from Florence as you explore Siena, San Gimignano, and Chianti—enjoy free time and a winery lunch with local craft tastings.

  • Stop at Siena and allow it to charm you with its Gothic elegance, narrow winding lanes, and the stunning shell-shaped Piazza del Campo. It’s small enough to explore in a few hours, yet packed with character.

  • 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.

from
€53.10
Siena cityscape with historic buildings and lush greenery during Chianti wine tour.
Tour guide speaking to tourists in a historic street during Pisa, Siena, and San Gimignano day trip.
Woman on a historic balcony with frescoes in San Gimignano, Italy.
Pisa Cathedral and Baptistery with tourists exploring the square.
Women posing playfully with the Leaning Tower of Pisa in Italy.
Bus traveling through Chianti vineyards during Florence wine tour.
Aerial view of Chianti winery with vineyards and Tuscan landscape.
Tourists enjoying a wine tasting experience in Tuscany during a Pisa, Siena, and San Gimignano day trip.
Wine bottles and Italian appetizers on a table during a Pisa, Siena, San Gimignano & Chianti day trip.
Stone buildings in a sunny Tuscan village square, part of the Highlights of Tuscany tour.
Siena Cathedral facade with tourists during the day in Siena, Italy.
Tour group inside Siena Cathedral with striped columns and stained glass window.
Tour group with guide at Piazza del Campo, Siena, Italy, with historic buildings in background.
Free cancellation
Instant confirmation
12 hr
3 more
  • Take a round-trip from Florence to explore Pisa, San Gimignano, and Siena, with photo ops at the Leaning Tower, a Tuscan lunch, and an optional guided cathedral tour at Siena.

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

  • 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.

More details

  • Take a round-trip from Florence to explore Pisa, San Gimignano, and Siena, with photo ops at the Leaning Tower, a Tuscan lunch, and an optional guided cathedral tour at Siena.

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

  • 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.

from
€65
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 session in Chianti, Italy with various oils and bread samples.
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
4 hr 30 min
3 more
  • Journey from Florence into the heart of Chianti for sommelier-led tastings, exclusive winery and olive oil mill visits, and a gourmet Tuscan lunch—all in one unforgettable experience.

  • Travel in comfort aboard a spacious luxury vehicle through the scenic Chianti countryside, also known as the 'land of the black rooster'.

  • Stop at an olive oil mill to sample Italy’s liquid gold straight from the source.

  • Visit three unique wineries, each offering a guided experience from vineyard to cellar. Enjoy a traditional Tuscan lunch, thoughtfully paired with select regional pours for a perfect taste of the territory.

  • Get personalized attention throughout this semi-private tour, making it more intimate and enriching than a standard group outing.

More details

  • Journey from Florence into the heart of Chianti for sommelier-led tastings, exclusive winery and olive oil mill visits, and a gourmet Tuscan lunch—all in one unforgettable experience.

  • Travel in comfort aboard a spacious luxury vehicle through the scenic Chianti countryside, also known as the 'land of the black rooster'.

  • Stop at an olive oil mill to sample Italy’s liquid gold straight from the source.

  • Visit three unique wineries, each offering a guided experience from vineyard to cellar. Enjoy a traditional Tuscan lunch, thoughtfully paired with select regional pours for a perfect taste of the territory.

  • Get personalized attention throughout this semi-private tour, making it more intimate and enriching than a standard group outing.

from €119
€89.25

25% off

Sommelier pouring wine into a glass at a vineyard in Tuscany, Italy.
Florence to Chianti tour with vineyard views and two wine tastings in Tuscany, Italy.
Chianti vineyard tour with wine tastings near Florence, Italy.
Chianti wine region vineyard with guided tour group tasting wine in Florence, Italy.
Florence to Chianti tour with vineyards and two wine tastings in Tuscany.
Chianti vineyards with wine barrels, part of a guided tour featuring two wine tastings in Florence, Italy.
Chianti vineyard with wine tasting tour near Florence, Italy.
Chianti vineyards with wine barrels, part of a guided tour featuring two wine tastings in Florence, Italy.
Free cancellation
Instant confirmation
5 hr
1 more
  • Sample superior Chianti blends 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.

More details

  • Sample superior Chianti blends 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.

from €55
€46.75

15% off

Cooking class in Florence making fresh pasta and sauces with lunch or dinner included.
Cooking class in Florence making fresh pasta and sauces with lunch or dinner.
Cooking class participants making fresh pasta in Florence kitchen.
Cooking class in Florence making fresh pasta and sauces with lunch or dinner.
Cooking class participants making fresh pasta in Florence kitchen.
Cooking class participants making fresh pasta in Florence kitchen.
Free cancellation
3 hr
Mobile ticket
1 more
  • Learn the art of pasta-making in the 3-hour cooking class led by a professional chef, amidst the stunning Chinati hills.

  • Discover the secrets to make the perfect ravioli, tagliatelle, cappelletti, and gnocchi as you sip on refreshing drinks.

  • Indulge in a meal curated with local cold cuts, cheeses, pasta prepared by you and pair the meal with a complementary drink and dessert.

  • Get exclusive recipes from the chef and take home a slice of Italian gastronomy.

More details

  • Learn the art of pasta-making in the 3-hour cooking class led by a professional chef, amidst the stunning Chinati hills.

  • Discover the secrets to make the perfect ravioli, tagliatelle, cappelletti, and gnocchi as you sip on refreshing drinks.

  • Indulge in a meal curated with local cold cuts, cheeses, pasta prepared by you and pair the meal with a complementary drink and dessert.

  • Get exclusive recipes from the chef and take home a slice of Italian gastronomy.

from
€120

Millions love heading out with us

Manish Pandya
US

Manish

5/5
United States
Hassle free experience with Headout, Ciao Florence tour to Chianti wineries was great and definitely value for money. Clean airconditioned bus, English speaking guide and no pressure wine tasting!
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.
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.
Megan Pattison
AU

Megan

5/5
Australia
Unfortunately this wasn't the tour we did as the company changed us onto another tour. The bus was comfortable and the little town of Greve in Chianti which we stopped in was very charming. I bought a gorgeous ring at the jewelers, my Italian ring which will remind me constantly of th wonderful holiday. The dinner was in the vineyard, the sun was a bit bright for some at the table. The food was amazing and the wines paired beautifully.
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
Adrianus WMM van de Ven

Adrianus

4/5
Supervisors Martha and Julio provided perfect guidance. Clear in information and always approachable. TOP With a wine company, we expected a winery in the countryside. This was a factory site. So ambience was a bit less, despite the enthusiastic employee of the winery. Nice and enthusiastic. Despite the severe thunderstorm in Siena we had a nice day.
Robin Bouvier
US

Robin

4/5
United States
We loved the three beautiful cities we visited, including the crown of Tuscany which wasn't on the itinerary. Paying to walk on the city walls was interesting and views were good, but we were on metal bridges, not the actual walls. There are two different access points so be sure to try both. Lunch was at a restaurant with a very small vineyard where we could walk and take photos. The tastings were all good but primarily a sales pitch. The pasta lunch was just ok. If you take the cathedral tour in Siena (recommended but additional cost) make sure you know how to get back to the meeting point!
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.
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