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Top things to do 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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Slide 1 of 7, Dirt road leading to a villa surrounded by cypress trees in Chianti, Tuscany.
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.

From Florence: Chianti Wineries Tour with Wine Tasting

5 hrs
1 more

  • Escape Florence for the rolling vineyards and scenic countryside of Tuscany’s celebrated Chianti wine region.

  • Visit 2 traditional Chianti wineries and enjoy 6 wine tastings with snacks, including regional wines and local flavors.

  • Learn about Chianti’s winemaking traditions, grape varieties, and production methods from expert hosts during your visits.

  • Travel comfortably with round-trip AC coach transfers, onboard Wi-Fi, and a licensed tour escort throughout the experience.

  • Enjoy a relaxed group experience with fellow wine lovers while discovering Tuscany’s iconic vineyard landscapes.

More details

  • Escape Florence for the rolling vineyards and scenic countryside of Tuscany’s celebrated Chianti wine region.

  • Visit 2 traditional Chianti wineries and enjoy 6 wine tastings with snacks, including regional wines and local flavors.

  • Learn about Chianti’s winemaking traditions, grape varieties, and production methods from expert hosts during your visits.

  • Travel comfortably with round-trip AC coach transfers, onboard Wi-Fi, and a licensed tour escort throughout the experience.

  • Enjoy a relaxed group experience with fellow wine lovers while discovering Tuscany’s iconic vineyard landscapes.

from
€33.15
Slide 1 of 9, Visitors exploring wine barrels in a Chianti cellar during a guided tour.
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.

From Florence: Chianti Countryside & Olive Grove Semi-Private Tour with Lunch & Gourmet Pairings

4 hrs 30 mins - 9 hrs
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 Original price€149
€107.28

28% off

Slide 1 of 13, Siena cityscape with historic buildings and lush greenery during Chianti Half Day Wine Tasting Tour.
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.

From Florence: Pisa, Siena, San Gimignano & Chianti Day Trip with Wine Tasting & Lunch

11 hrs 30 mins - 12 hrs
2 more

  • Explore four of Tuscany’s most iconic destinations in one well-planned day trip from Florence.

  • Enjoy free time in Pisa, San Gimignano, and Siena to explore at your own pace.

  • Savor authentic Tuscan flavors with a winery visit, wine tastings, and a traditional local meal.

  • Upgrade your experience with guided tours of Siena and its cathedral or access to Pisa’s famous tower.

  • Travel comfortably with round-trip AC coach transfers and a multilingual tour leader throughout.

More details

  • Explore four of Tuscany’s most iconic destinations in one well-planned day trip from Florence.

  • Enjoy free time in Pisa, San Gimignano, and Siena to explore at your own pace.

  • Savor authentic Tuscan flavors with a winery visit, wine tastings, and a traditional local meal.

  • Upgrade your experience with guided tours of Siena and its cathedral or access to Pisa’s famous tower.

  • Travel comfortably with round-trip AC coach transfers and a multilingual tour leader throughout.

from
€67.15
Slide 1 of 7, Piazza del Campo in Siena with Torre del Mangia and Palazzo Pubblico.
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.

From Florence: Siena, San Gimignano & Chianti Day Trip with Wine Tastings

10 hrs 30 mins - 11 hrs 30 mins
1 more

  • Visit Siena, San Gimignano, and Chianti in one well-paced day trip from Florence.

  • Enjoy a winery visit in the Chianti countryside with 3 wine tastings included.

  • Get free time in both Siena and San Gimignano to explore at your own pace.

  • Upgrade to a guided walking tour of Siena for deeper insight into its history and landmarks.

  • Travel comfortably with round-trip transfers and a multilingual tour leader.

More details

  • Visit Siena, San Gimignano, and Chianti in one well-paced day trip from Florence.

  • Enjoy a winery visit in the Chianti countryside with 3 wine tastings included.

  • Get free time in both Siena and San Gimignano to explore at your own pace.

  • Upgrade to a guided walking tour of Siena for deeper insight into its history and landmarks.

  • Travel comfortably with round-trip transfers and a multilingual tour leader.

from
€65
Slide 1 of 9, Aerial view of San Gimignano with medieval towers and surrounding countryside.
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.

From Florence: Siena & San Gimignano Day Trip with Wine Tastings & Lunch

9 hrs - 11 hrs
2 more

  • Discover two of Tuscany’s most iconic hill towns in one relaxed day trip from Florence.

  • Enjoy free time in both Siena and San Gimignano to explore at your own pace.

  • Taste regional flavors with a winery visit, 3 wine tastings, and a traditional Tuscan meal.

  • Upgrade to a guided Siena tour with optional Cathedral access for a deeper cultural experience.

  • Travel comfortably with round-trip AC transport and a multilingual tour leader.

More details

  • Discover two of Tuscany’s most iconic hill towns in one relaxed day trip from Florence.

  • Enjoy free time in both Siena and San Gimignano to explore at your own pace.

  • Taste regional flavors with a winery visit, 3 wine tastings, and a traditional Tuscan meal.

  • Upgrade to a guided Siena tour with optional Cathedral access for a deeper cultural experience.

  • Travel comfortably with round-trip AC transport and a multilingual tour leader.

from
€79
Slide 1 of 11, Guide talking to a couple in front of Pisa Cathedral and Leaning Tower, Italy.
Guide talking to a couple in front of Pisa Cathedral and Leaning Tower, Italy.
Women posing playfully with the Leaning Tower of Pisa in Italy.
Pisa Cathedral and Baptistery with tourists exploring the square.
Tour guide speaking to tourists in a historic street during Pisa, Siena, and San Gimignano day trip.
San Gimignano skyline with medieval towers under a blue sky, Tuscany, Italy.
Tourists boarding air-conditioned coach bus for transfer to Montserrat Monastery.
Tour group with guide at Piazza del Campo, Siena, Italy, with historic buildings in background.
Siena Cathedral facade with tourists during the day in Siena, Italy.
Visitors inside Pisa Cathedral, Italy, admiring ornate ceiling and arches.
Aerial view of San Gimignano towers and surrounding Tuscan countryside.
Torre Grossa in San Gimignano's historic square with medieval architecture.

From Florence: Small Group Pisa, Siena, San Gimignano & Chianti Day Trip

11 hrs 30 mins - 12 hrs 15 mins
2 more

  • Explore Pisa, Siena, San Gimignano, and Chianti in a small group of no more than 20 guests for a more intimate and relaxed experience.

  • Enjoy free time in Tuscany's most iconic towns, with fewer people and more opportunities to connect with your tour leader and fellow travelers.

  • Visit a Chianti winery and sample three regional wines while learning about the traditions behind Tuscany's world-famous winemaking.

  • Sit down to a traditional Tuscan lunch surrounded by rolling vineyards and postcard-worthy countryside scenery.

  • Upgrade to a guided tour of Siena for expert insights into its medieval history, famous piazza, and centuries-old traditions.

More details

  • Explore Pisa, Siena, San Gimignano, and Chianti in a small group of no more than 20 guests for a more intimate and relaxed experience.

  • Enjoy free time in Tuscany's most iconic towns, with fewer people and more opportunities to connect with your tour leader and fellow travelers.

  • Visit a Chianti winery and sample three regional wines while learning about the traditions behind Tuscany's world-famous winemaking.

  • Sit down to a traditional Tuscan lunch surrounded by rolling vineyards and postcard-worthy countryside scenery.

  • Upgrade to a guided tour of Siena for expert insights into its medieval history, famous piazza, and centuries-old traditions.

from
€149
Slide 1 of 8, Pouring red wine into a glass in a vineyard setting.
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.

Chianti Region Guided Tour with Local Tastings and Vineyards

5 hrs

  • 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
Slide 1 of 6, Participants making fresh pasta in a cooking class, measuring ingredients into bowls.
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.

Pasta Cooking Class in Chianti with Food

3 hrs
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
Slide 1 of 7, Wine glasses raised in a toast during a Florence wine experience in Chianti Hills.
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.

Taste of Chianti: Countryside Flavors & Vineyard Tour and Tastings

5 hrs
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
€33.15

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1

Leaning Tower of Pisa with tourists, part of Florence to Pisa tour.

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2

Tuscany landscape with cypress trees and farmhouse in San Quirico d'Orcia, Italy.

Florence To Tuscany Tours

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3

Medieval towers of San Gimignano in Tuscany, Italy, seen on Florence to Chianti tours.

Florence To Chianti Tours

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

4

Siena's Piazza del Campo with historic buildings, part of Florence to Siena tours.

Florence To Siena Tours

Take a day trip from Florence to Siena, a UNESCO medieval gem and top destination in Tuscany.

5

Leaning Tower of Pisa with tourists, part of Florence to Pisa tours.

Florence To Pisa Tours

Explore the city of Pisa, home to the Leaning Tower, grand cathedrals, and historic squares.

6

Backpacker descending steps with Vernazza view in Cinque Terre National Park, Italy.

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What our guests say

Zuzanna B

Belgium
Couple
Jul 2026

+2 more

We did the Chianti wine tour and it was incredible! Our guide Ms Ezgi was very enthousiast to share her knowledge of the region with us in a very professional way.The wines were very tasty. The views were breath taking. Really recommend doing this tour especially if you are a Witcher 3 Blood and Wine fan!!

From Florence: Chianti Wineries Tour with Wine Tasting

Victoria H

Colombia
Couple
Jun 2026
Everything from the beginning was awesome. Logistic, samples, places. All the people was so nice and welcoming. I really enjoy this experiencie with my husband in our honeymoon trip

From Florence: Chianti Wineries Tour with Wine Tasting

Christopher M

Couple
Jun 2026

+1 more

Enjoyed being taken to places with a really great driver. The bus guide was very good especially impressed with 3 languages skill set. The wine tasting venue was great and very entertaining. Sienna guided tour was excellent. Great guide. Would have happily sacrificed Pisa for longer at vineyard as this seemed a little rushed. It was over lunch we gelled as a group and made new friends. Wasn't so impressed with the amount of walking involved from bus to venue. It didn't help that the temperatures were 35°C. Overall an excellent tour.

From Florence: Pisa, Siena, San Gimignano & Chianti Day Trip with Wine Tasting & Lunch

Melissa A

Australia
Couple
Jun 2026
Beautiful stop spots rich in art and culture, especially Sienna... and the wine tasting was fantastic! Our guide John was great too.

From Florence: Pisa, Siena, San Gimignano & Chianti Day Trip with Wine Tasting & Lunch

Yang Z

China
Couple
Jun 2026

+6 more

Alex is an incredibly warm and friendly guide! We absolutely loved this day trip to Siena, San Gimignano, and Monteriggioni. For me, visiting the actual locations from Ezio Auditore’s story was a real pilgrimage. As for the €22 lunch, it was fine, but if you prefer more freedom, feel free to choose your own restaurant—just make sure to be on time for the meeting. Finally, if you have the chance to visit a winery in Chianti, you absolutely must try Firmina. It’s a truly interesting wine to drink!

From Florence: Siena, San Gimignano & Chianti Day Trip with Wine Tastings

Dai V

Canada
Group
Jul 2026
The tour was professionally organized from start to finish. Everything ran perfectly on schedule, with departures and arrivals right on time. Our guide was knowledgeable, engaging, and had a great sense of humor, which made the journey even more enjoyable. A special mention goes to our driver, who demonstrated exceptional skill and experience navigating winding roads and narrow streets. We felt safe and comfortable throughout the entire trip. The wine tasting was excellent, and the selection of vineyards was well chosen. As with our previous experiences, Headout once again delivered a fantastic tour. Thank you for providing such a memorable experience and helping make our holiday even more special.

Chianti Region Guided Tour with Local Tastings and Vineyards

Lisa S

Couple
Jul 2026
Samuel and Elvis were a very pleasant team. Samuel was always empathetic and friendly. He patiently answered every question and went out of his way to ensure the guests’ comfort. It was also very important to him that everyone received all the information in a timely manner. His fun facts about the places we visited were very entertaining. Thank you for the wonderful experience.

From Florence: Siena & San Gimignano Day Trip with Wine Tastings & Lunch

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