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#4 out of 29 in Florence

Florence To Chianti Tours

Leave the city behind for rolling hills, vineyard visits, and olive oil tastings in Tuscany’s Chianti region.

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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.
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 an e-bike tour.
Free cancellation
Book now, pay later
5 hr
  • 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 €55
€46.75

15% off

Siena Cathedral facade with visitors in Piazza del Duomo, Italy.
Santa Maria della Scala museum facade in Siena, Italy, with visitors in the courtyard.
Winding road through vineyards on Via Chiantigiana, Tuscany.
Vineyards in Chianti landscape during wine tasting tour.
Chianti winery tasting room with tables set for wine sampling.
Group toasting with wine at a winery table surrounded by barrels.
Siena cityscape with historic buildings and lush greenery during Chianti Half Day Wine Tasting Tour.
Cypress-lined road through Tuscan countryside with rolling hills.
Man harvesting grapes in a Tuscany vineyard.
Passengers seated inside a tour bus traveling from Paris to Mont St. Michel's Abbey.
Free cancellation
Book now, pay later
7 hr
2 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

Siena cityscape with historic buildings and lush greenery during Chianti Half Day Wine Tasting Tour.
Women posing playfully with the Leaning Tower of Pisa in Italy.
Pisa Cathedral and Baptistery with tourists exploring the square.
Stone buildings in a sunny Tuscan village square, part of the Highlights of Tuscany tour.
People dining at a long table during Pisa, Siena, and San Gimignano day trip.
Visitors at the steps of a historic church in San Gimignano, Italy.
Bus traveling through Chianti vineyards during Florence wine tour.
Wine bottles and Italian appetizers on a table during a Pisa, Siena, San Gimignano & Chianti day trip.
Tourists enjoying a wine tasting experience in Tuscany during a Pisa, Siena, and San Gimignano day trip.
Siena Cathedral facade with tourists during the day in Siena, Italy.
Siena Cathedral interior with striped columns and ornate vaulted ceiling.
Tourists inside Siena Cathedral admiring frescoes and architecture, Italy.
Tour guide speaking to tourists in a historic street during Pisa, Siena, and San Gimignano day trip.
Free cancellation
Book now, pay later
12 hr
2 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
Piazza del Campo in Siena with Torre del Mangia and Palazzo Pubblico.
Streets of San Gimignano with historic stone buildings and tourists exploring.
Vineyards and olive groves in Chianti region, Tuscany, Italy.
Hand holding a glass of rosé wine in a Chianti vineyard during an e-bike tour.
Wine barrels in a cellar during Chianti wine tasting tour from Florence.
Tour guide holding a sign in a Chianti village during a wine tour from Florence.
Bus interior with passengers traveling from Tromso to Skjervoy.
Free cancellation
Book now, pay later
11 hr 30 min
2 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
€85
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
Book now, pay later
9 hr
1 more
  • Relax on an AC coach from Florence as you explore Siena and San Gimignano. Enjoy free time in both these cities and explore them independently.

  • An English-speaking tour leader will accompany you throughout your day trip to enrich your visit with insider tips, trivia, and more.

  • 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.

  • If you book this tour in August 2025, enjoy a complimentary meal with wine tasting and a guided tour of Siena.

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

More details

  • Relax on an AC coach from Florence as you explore Siena and San Gimignano. Enjoy free time in both these cities and explore them independently.

  • An English-speaking tour leader will accompany you throughout your day trip to enrich your visit with insider tips, trivia, and more.

  • 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.

  • If you book this tour in August 2025, enjoy a complimentary meal with wine tasting and a guided tour of Siena.

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

from
€59
Visitors exploring wine barrels in a Chianti cellar during a guided tour.
Group listening to a guide in a Chianti wine cellar during a wine and olive oil tour.
Group enjoying wine tasting session in Chianti with guide explaining wine details.
Group enjoying wine tasting during Chianti tour.
Cheese, tomatoes, and vegetables on a wooden platter during Chianti wine and olive oil tour.
Olive oil being poured into tasting glasses during a Chianti experience.
Group enjoying wine tasting outdoors in Chianti.
Group enjoying wine tasting outdoors in Chianti countryside.
Private transfer service at Narita Airport with passengers in a luxury vehicle.
Free cancellation
Book now, pay later
4 hr 30 min
2 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 €149
€111.75

25% off

Pouring red wine into a glass in a vineyard setting.
People enjoying wine tasting in a vineyard in the Chianti region, Florence.
Chianti signpost in vineyard, Florence to Chianti wine region tour.
Chianti vineyard landscape with rows of grapevines under a clear sky.
Grapes on a vine in the Chianti wine region, Tuscany.
Man harvesting grapes in Chianti vineyard during guided wine tour.
Wine barrels and dining setup in a Chianti vineyard, Florence tour.
Bottles of wine displayed on a shelf in the Chianti wine region.
Free cancellation
Book now, pay later
5 hr
  • 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

Wine glasses raised in a toast during a Florence wine experience in Chianti Hills.
Two people enjoying grape picking in the Chianti Hills vineyard.
Stone church facade in Chianti Hills, Italy, under a blue sky.
Grapes harvested in Chianti Hills vineyard for wine tasting tour.
Vineyard with ripe grapes in the Chianti Hills, Italy.
Vineyards in Chianti Hills, Tuscany, with rolling hills and cypress trees in the background.
Wine cellar with tasting table and shelves of wine bottles in Chianti Hills.
Free cancellation
Book now, pay later
6 hr
1 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
Participants making fresh pasta in a cooking class, measuring ingredients into bowls.
Fresh pasta on a plate during a cooking class.
Cooking class participants making fresh pasta with chef guidance.
Hands rolling fresh pasta dough in a cooking class.
Fresh pasta making class with chef guiding participants in rolling dough.
Making fresh pasta in a cooking class with a chef and participant.
Free cancellation
Book now, pay later
3 hr
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

Dionne Rochelle Stroter
US

Dionne

United States
Jul 2025
5/5
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+1 more

This was an impromptu excursion for us on an unexpected free day during our vacation and it was wonderful. Our hotel was near the meeting point at the train station and the check in process was very easy. Our tour guide Dora was knowledge and friendly. We visited two wineries and had a great time tasting the wines and snacks provided. At the second stop our host Costanza was an amazing storyteller and very entertainment. It was about 45 minutes from Florence and overall the tour lasted about 5 hours. It was great value for the price and we were so glad we signed up.
Manish Pandya
US

Manish

United States
Jul 2025
5/5
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review-image
review-image

+1 more

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

Nov 2022
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

Jul 2022
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

Australia
Jul 2025
5/5
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

India
Jun 2023
5/5
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

Jul 2025
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

United States
May 2025
4/5
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!
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