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Chianti tours from Florence
The classic experience – two vineyard visits garnished by wine and fresh local munchies!
- Board a comfortable AC bus from Florence for your wine-tasting trip to Chianti, the enchanting namesake of its famous Italian red.
- Sample delicious wines at two Chianti Classico vineyards, and taste other signature products with some silky olive oil!
- Learn how the production process works as you tour the historic cellars and fields in your chosen language, from a variety of options.
- Soak in the Tuscan countryside dotted with farms and olive groves on this classic vinery experience.
The classic experience – two vineyard visits garnished by wine and fresh local munchies!
- Board a comfortable AC bus from Florence for your wine-tasting trip to Chianti, the enchanting namesake of its famous Italian red.
- Sample delicious wines at two Chianti Classico vineyards, and taste other signature products with some silky olive oil!
- Learn how the production process works as you tour the historic cellars and fields in your chosen language, from a variety of options.
- Soak in the Tuscan countryside dotted with farms and olive groves on this classic vinery experience.
Inclusions
- Half-day trip around Chianti
- Expert local guide in English, Spanish, Italian, Portuguese, or Chinese
- Pick up from Florence
- Round-trip AC bus transfer
- 2 vineyard visits and wine tastings with snacks
- Tip: You have the chance to buy authentic Tuscan products right at the source! Carry a little extra cash if you'd like to take home a treat.
- This experience is not accessible by wheelchair and pram/strollers.
- Safety is a priority so the wine tasting experience is restricted for guests under the age of 18 years.
- Guests under the age of 18 years can join the tour if they are each accompanied by at least one adult.
- You can cancel these tickets up to 48 hours before the experience begins and get a full refund.
Reviews
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3.9
10 ratings
4
3
2
0
1
What our guests say
Mara
Nov 2024Verified booking
The tour guide and bus driver were so patient and nice as they waited for us to get on the bus since we were late due to transportation issues.
CLAUDIO
Oct 2024Verified booking
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
Sabire
Oct 2024Verified booking
Butique winery visit was indeed great!
Michael
Sep 2024Verified booking
Comfortable and pleasant presentation both vinyards
Joanne
Sep 2024Verified booking
William
Sep 2024Verified booking
Vardaan
Aug 2024Verified booking
Hariom
Jun 2024Verified booking
Adriana
Apr 2024Verified booking
Itinerary
TOTAL DURATION7 hours 30 minutes
MODE OF TRANSFERA/C Bus
START POINT
Piazzale Montelungo
Set off along the scenic Chiantigiana road from your meeting point in central Florence.
78.3 km
71 minutes
1
Siena
90 min
2 attractions
Get ample free time to immerse yourself in the city's medieval charm. There's lots to explore – like the world's oldest bank, Banca Monte dei Paschi!
Things to do
1. Medici Fortress
Take a stroll to this red-bricked fort, admire the surrounding Rimembranza Park, and gaze out at panoramas of Siena.
2. Torre del Mangia
In the main square Plaza Campo stands one of ancient Italy's tallest towers, right next to Siena's town hall.
45.5 km
59 minutes
2
Chianti Classico
Venture into the heart of Chianti and discover a picturesque winery set amidst a sprawling estate.
Things to do
Dinner and Wine Tasting
Dinner
Enjoy fresh seasonal and local products like salami, bruschetta and a traditional pasta dish, enhanced by carefully selected wines, under the dazzling Tuscan sunset.
27.8 km
45 minutes
3
END POINT
Piazzale Montelungo
An afternoon in Siena followed by a delectable dinner and wine tasting in Chianti!
- Cruise the 'Via Chiantigiana' on a cozy AC bus departing Florence, with friendly hosts onboard fluent in English or Spanish.
- Independently explore Siena, from its Gothic cathedral to the off-beat Santa Maria della Scala museum.
- Make your way to a rustic winery in the heart of Chianti, where traditional pasta and other seasonal dishes are accompanied by the perfect wines!
An afternoon in Siena followed by a delectable dinner and wine tasting in Chianti!
- Cruise the 'Via Chiantigiana' on a cozy AC bus departing Florence, with friendly hosts onboard fluent in English or Spanish.
- Independently explore Siena, from its Gothic cathedral to the off-beat Santa Maria della Scala museum.
- Make your way to a rustic winery in the heart of Chianti, where traditional pasta and other seasonal dishes are accompanied by the perfect wines!
Inclusions
- Half-day trip around Siena and Chianti
- Expert local guide in English or Spanish
- Pick up from Florence
- Round-trip AC bus transfer
- Vineyard visit, wine tasting, and dinner in Chianti
- Tip: You can walk along the walls of the Medici Fortress in Siena for excellent views of the city and countryside.
- This experience is not accessible by wheelchair and pram/strollers.
- Safety is a priority so the wine tasting experience is restricted for guests under the age of 18 years.
- Guests under the age of 18 years can join the tour if they are each accompanied by at least one adult.
- You can cancel these tickets up to 24 hours before the experience begins and get a full refund.
Itinerary
TOTAL DURATION10 hours 30 minutes
MODE OF TRANSFERA/C Bus
START POINT
Central Florence
Check your final voucher for the exact location in Florence where you board your spacious coach and start your adventure.
78.3 km
71 minutes
1
Siena
1 attractions
At your first stop, set off on a guided tour through the main squares. Admire the architecture of Torre del Mangia (Eater's Tower) at the lively Plaza del Campo.
Things to do
Palazzo Pubblico
Discover a palace that serves as a town hall, set in the bustling main square of Plaza del Campo.
41.7 km
46 minutes
2
San Gimignano
1 attractions
Get free time to explore the maze of cobbled streets, looming towers, and the many local artisan shops at this hilltop village known as a 'Medieval Manhattan'.
Things to do
Piazza della Cisterna
This triangular sloping plaza is surrounded by ancient skyscrapers.
45.9 km
57 minutes
3
Chianti Classico
1 activities
Head to a charming vineyard in the heart of the Chianti region.
Things to do
Vineyard tour & wine tasting
Included in price
Visit a rustic estate, where a wine producer takes you through the grape-filled vineyards and cellars. Indulge in a few samples of the wines with local specialty snacks and fresh olive oil.
29.1 km
50 minutes
4
END POINT
Central Florence
The essential Tuscany trip! Discover Siena, San Gimignano, and Chianti, and sip the best of wines.
- Sit back, relax, and enjoy the comfortable GT coach ride from Florence and back with multilingual support on deck.
- Walk around the Palazzo Pubblico town hall and Mangia Tower in the Piazza del Campo on a guided tour of Siena.
- Interested in ancient skyscrapers encircled by 13th-century walls? Wander the UNESCO World Heritage Site of San Gimignano at your whim.
- Now, bring on the wine! Stroll through a local Chianti estate and hear the secrets behind its magic as you drink and munch.
The essential Tuscany trip! Discover Siena, San Gimignano, and Chianti, and sip the best of wines.
- Sit back, relax, and enjoy the comfortable GT coach ride from Florence and back with multilingual support on deck.
- Walk around the Palazzo Pubblico town hall and Mangia Tower in the Piazza del Campo on a guided tour of Siena.
- Interested in ancient skyscrapers encircled by 13th-century walls? Wander the UNESCO World Heritage Site of San Gimignano at your whim.
- Now, bring on the wine! Stroll through a local Chianti estate and hear the secrets behind its magic as you drink and munch.
Inclusions
- Full-day trip around Siena, San Gimignano, and Chianti
- Multilingual assistance on board
- Pick up from Florence
- Round-trip AC coach transfer
- Expert English-speaking guide in Siena
- Vineyard visit and wine tasting in Chianti
Exclusions
- Lunch
- Tip: When in San Gimignano, seek out the Rocca di Montestaffoli. This old fortress offers a quieter panoramic vantage with lovely gardens that many tourists miss.
- This experience is not accessible by wheelchair and pram/strollers.
- Safety is a priority so the wine tasting experience is restricted for guests under the age of 18 years.
- Guests under the age of 18 years can join the tour if they are each accompanied by at least one adult.
- You can cancel these tickets up to 24 hours before the experience begins and get a full refund.
Itinerary
TOTAL DURATION10 hours 30 minutes
MODE OF TRANSFERA/C Bus
START POINT
Central Florence
Meet your fellow travel mates and set off from the heart of Florence by AC coach.
78.3 km
71 minutes
1
Siena
2 attractions
Independently uncover the historic districts of Siena, or go on a guided tour of the city center and optionally its cathedral.
Things to do
1. Banca Monte dei Paschi
Exploring by yourself? Be sure to check out the oldest bank in the world! It was founded 500 years ago and remains one of Italy's largest banking institutions.
2. Siena Cathedral
Nestled in Piazza del Duomo is the magnificent cathedral, a Gothic-Romanesque masterwork. Select the guided tour with entry to admire the mosaic floors and frescoes within.
45.5 km
59 minutes
2
Chianti Classico
1 activities
Drive along the gentle slopes of Chianti and head into a vintage wine estate.
Things to do
1. Vineyard tour & wine tasting
Included in price
Be welcomed to the organic winery with a glass of sparkling and immerse yourself on a tour of its wine cellar.
2. Tuscan lunch
Lunch
Smack on an exquisite 3-course lunch, accompanied by four delightful wines.
46.4 km
55 minutes
3
San Gimignano
1 attractions
At your leisure, traverse this hilltop city, from its old town's 13th-century walls to its skyline filled with high rises.
Things to do
Torre Grossa
Situated in Piazza Duomo, this UNESCO World Heritage Site is the tallest of San Gimignano's medieval skyscrapers.
61.1 km
70 minutes
4
END POINT
Central Florence
Indulge your appetite on a trip to Siena, San Gimignano, and Chianti with lunch and wines included!
- Freely roam through Siena by yourself, or choose a guided tour of the city center. Upgrade to enter the iconic Siena Cathedral!
- Drop by a winery nestled in the rolling hills of Chianti and dig into a sumptuous 3-course lunch paired with an array of fine wines.
- Gaze up at the towering structures of San Gimignano as you learn why it's called the 'Manhattan of the Middle Ages'.
- Relax to and from Florence aboard an AC coach. Between April and October, you may also stop at the medieval fortress commune of Monteriggioni!
Indulge your appetite on a trip to Siena, San Gimignano, and Chianti with lunch and wines included!
- Freely roam through Siena by yourself, or choose a guided tour of the city center. Upgrade to enter the iconic Siena Cathedral!
- Drop by a winery nestled in the rolling hills of Chianti and dig into a sumptuous 3-course lunch paired with an array of fine wines.
- Gaze up at the towering structures of San Gimignano as you learn why it's called the 'Manhattan of the Middle Ages'.
- Relax to and from Florence aboard an AC coach. Between April and October, you may also stop at the medieval fortress commune of Monteriggioni!
Inclusions
- Full-day trip around Siena, San Gimignano, and Chianti
- Multilingual assistance on board
- Pick up from Florence
- Round-trip AC coach transfer
- Vineyard visit, wine tasting, and lunch in Chianti
- Guided tour of Siena city center (if selected)
- Guided tour of Siena Cathedral and city center (if selected)
- Tip: It's possible to walk along the 2176-metre perimeter of the second circle of city walls that mark the historical centre of San Gimignano.
- This experience is not accessible by wheelchair and pram/strollers.
- Safety is a priority so the wine tasting experience is restricted for guests under the age of 18 years.
- Guests under the age of 18 years can join the tour if they are each accompanied by at least one adult.
- Please note that the order of visits is subject to change.
- For entry to Siena Cathedral, all guests must wear clothing that covers the knees and shoulders.
- You can cancel these tickets up to 24 hours before the experience begins and get a full refund.
Reviews
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4.1
834 ratings
523
130
23
46
112
What our guests say
NATALIA
Dec 2024Verified booking
The tour is phenomenal, I did not like that the bus does not have a bathroom and that the tasting the person who gave it spoke too fast was not understood much, otherwise perfect.
View original review in Spanish
Andrew
Nov 2024Verified booking
The visit to Siena, San Gimignano & the Chianti lunch & wine tasting were all very good. The tour leader was excellent.
Nuria
Sep 2024Verified booking
The villages visited were wonderful, the time to visit them perfect and the guides Marta. Fabrizio and Ferdinado, unbeatable. The visit to the vineyards, the wine tasting and the fabulous lunch. Highly recommended!
View original review in Spanish
Antonia
Jul 2024Verified booking
Great experience, perfect length, great lunch & wine. The guide was the cherry on top, fascinating explanations about the places we saw, and even additional explanations about Florence and different things that we saw on the way. The bus trip itself is also a breath of fresh air and air conditioning in between sightseeing. The only tip: I think for european travelers, the 'winery' is obviously not a real winery but a business for tourist entertainment, especially because of the slightly pathetic comedy show pulled by the winery host, with bad jokes targeting directly North American tourists.
Kaminthia
Jun 2024Verified booking
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
Traci-Ann
Nov 2024Verified booking
The guide was excellent and the tour ran to time in all locations. Everything was as expected or better.
Rebecca
Oct 2024Verified booking
Fabulous guide, Sandro and driver, Fernando! The winery was also a big highlight. So much fun.
Andrea
Jul 2024Verified booking
Sandro and Catu very good guides. Plenty of free time to explore each place.
View original review in Spanish
Victor
Jun 2024Verified booking
It was very nice and well organized. The travel guide was very nice, helpful and informative.
Rozita
Nov 2024Verified booking
Cláudo
Oct 2024Verified booking
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Itinerary
TOTAL DURATION12 hours
MODE OF TRANSFERA/C Bus
START POINT
Central Florence
Head to the location mentioned on your final voucher and set off on your adventure.
84.5 km
77 minutes
1
Pisa
1 attractions
Stop by Pisa's Square of Miracles, where you will have time to admire the stunning Cathedral, Baptistery, Monumental Cemetery, and pose with the Leaning Tower.
Things to do
Leaning Tower of Pisa
78.8 km
81 minutes
2
San Gimignano
1 attractions
Nicknamed 'Manhattan of the Middle Ages', San Gimignano's tall, narrow towers create a modern skyline. Stroll by charming craftsmen’s shops along the cobbled stone streets and small squares.
Things to do
1. Tuscan lunch
Lunch
Fuel up with a traditional Tuscan lunch and wine pairings before hitting the streets of San Gimignano.
2. Duomo di San Gimignano
Admire the Collegiata di Santa Maria Assunta, a 12th-century church with frescoes by Ghirlandaio in its Santa Fina Chapel.
41.9 km
46 minutes
3
Siena
2 attractions
You can choose to either freely explore Siena, or avail a guided tour of the city center and maybe even its cathedral.
Things to do
1. Piazza del Campo
Traverse the main square, lying on the intersection of the three main roads that lead in and out of Siena.
2. Siena Cathedral
Nestled in Piazza del Duomo is the magnificent Gothic-Romanesque cathedral. Select the guided tour with entry to admire the mosaic floors and frescoes within.
77 km
78 minutes
4
END POINT
Central Florence
See the iconic Leaning Tower of Pisa, fill up on lunch with drinks in San Gimignano, and traverse Siena!
- Want to unravel three UNESCO Heritage gems from Florence in just one day? A trip to Pisa, San Gimignano, and Siena is the answer.
- At Pisa, walk along the Square of Miracles and get enough time for photo ops by the Leaning Tower!
- A hearty lunch with the finest wines at San Gimignano keeps your energy up as you uncover its 13th-century walls and stone skyscrapers.
- Fall in love with Siena's medieval streets and squares. Upgrade to a guided tour with an optional cathedral visit to get the most of your trip!
- Cruise to all destinations and back in a feature-packed AC vehicle that comes with friendly multilingual support.
See the iconic Leaning Tower of Pisa, fill up on lunch with drinks in San Gimignano, and traverse Siena!
- Want to unravel three UNESCO Heritage gems from Florence in just one day? A trip to Pisa, San Gimignano, and Siena is the answer.
- At Pisa, walk along the Square of Miracles and get enough time for photo ops by the Leaning Tower!
- A hearty lunch with the finest wines at San Gimignano keeps your energy up as you uncover its 13th-century walls and stone skyscrapers.
- Fall in love with Siena's medieval streets and squares. Upgrade to a guided tour with an optional cathedral visit to get the most of your trip!
- Cruise to all destinations and back in a feature-packed AC vehicle that comes with friendly multilingual support.
Inclusions
- Full-day trip around Pisa, San Gimignano, and Siena
- Multilingual assistance on board
- Pick up from Florence
- Round-trip AC coach transfer
- Lunch with wine in San Gimignano
- Guided tour of Siena city center (if selected)
- Guided tour of Siena Cathedral and city center (if selected)
- Tip: For the best gelato in San Gimignano, visit the award-winning Gelateria Dondoli in the main square. Don’t miss their signature Saffron and Pine Nut flavor.
- This experience is not accessible by wheelchair and pram/strollers.
- Safety is a priority so the wine tasting experience is restricted for guests under the age of 18 years.
- Guests under the age of 18 years can join the tour if they are each accompanied by at least one adult.
- Please note that the order of visits is subject to change.
- For entry to Siena Cathedral, all guests must wear clothing that covers the knees and shoulders.
- You can cancel these tickets up to 24 hours before the experience begins and get a full refund.
Reviews
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4.4
3.9K ratings
2.6K
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237
What our guests say
Maria
Oct 2024Verified booking
The complete package, very well organised and a brilliant tour guide can't remember her named but she was the English tour guide.
Juan
Sep 2024Verified booking
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
Alexis
Jul 2024Verified booking
This was one of the highlights of my trip! Our tour guide was excellent and very knowledgeable. Her English was also very good. Marco at Poggio ai Laghi (the winery) was hilarious and made the experience that much better! Definitely do this if you get a chance. Be prepared; this is a lot of walking, so wear very good shoes.
Rebecca
Jul 2024Verified booking
It was easy to be brought around, and I think all of the places we visited were good. The tour guide was also very good. I was, however, disappointed that there was a toilet on the bus and we weren't allowed to use it on a tour that went 12 hours. Also, the vegetarian meal was about half the size of the other meal for lunch.
ANGIE
Jun 2024Verified booking
It was a nice trip well organised by the tour managers . The main highlights of the trip were given in d bus before reaching a particular stop. However the only problem was the same thing was repeated in spanish and portuguese which went över the head!... the views of pisa, chianti and sam gimgnano worth the travel!! A long and tiring trip so plan the previous day accordingly so that next day u can enjoy your tour to fullest! Overall it was a lovely experience with our guides!
Abhaya
May 2024Verified booking
The guide was perfect, however I believe they should be a bit more strict with the timings. We were accompanied by a group who didn't stop talking at all. This meant we couldn't hear a bit of what the guide was saying in the bus.
Prachi
Jan 2024Verified booking
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.
Lidia
Dec 2024Verified booking
Everything was excellent. Only the part of the lunch in the vineyard that no one explained in Spanish.
View original review in Spanish
Kayhan
Oct 2024Verified booking
Perfect tour perfect guide, super
Oswaldo
Oct 2024Verified booking
Great guide, everything according to plan, punctuality and great cities
View original review in Portuguese
Heather
May 2024Verified booking
The scenery was amazing! And the guides were great. Not having air conditioning in the bus was a bummer
Sergey
Apr 2024Verified booking
Guide was perfect and very professional We got everywhere on time and even bad weather didint destroy our experience
Aparna
Apr 2024Verified booking
We loved the smooth transfers, wine tasting and the sienna tour
carolin
Mar 2024Verified booking
The tour guide Elisabetha and the bus driver Alexander were very good!
View original review in German
Megan
Feb 2024Verified booking
Lucca, our guide, made the tour so interesting. He was fabulous. Lucca was very knowledgeable and engaging.
Maura
Jan 2024Verified booking
These were beautiful areas in Tuscany to visit, and the logistics support was helpful. Guide was friendly.
Warnakulasuriya
Nov 2024Verified booking
Lilit
Oct 2024Verified booking
jaime
Oct 2024Verified booking
Aazmina
Oct 2024Verified booking
Vindhya
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Pruna
Aug 2024Verified booking
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Exclusive, in-depth, unforgettable! Get personalized attention, sommelier-selected tastings, and a mouthwatering lunch.
- Put your feet up in a spacious luxury vehicle from Florence to Chianti, learning all about the intriguing 'land of the black rooster'!
- A tour with samples at an olive oil mill and three wineries, from grove to cellar, gives you a taste of Italy's precious gastronomy.
- After discovering the diverse estates around the village, settle in for a quintessential Tuscan spread to go with your buzz!
Exclusive, in-depth, unforgettable! Get personalized attention, sommelier-selected tastings, and a mouthwatering lunch.
- Put your feet up in a spacious luxury vehicle from Florence to Chianti, learning all about the intriguing 'land of the black rooster'!
- A tour with samples at an olive oil mill and three wineries, from grove to cellar, gives you a taste of Italy's precious gastronomy.
- After discovering the diverse estates around the village, settle in for a quintessential Tuscan spread to go with your buzz!
Inclusions
- Small-group day trip around Chianti
- Pick up from Florence
- Round-trip Mercedes minibus or minivan transfers
- Guided tour of 1 olive oil mill & 3 wineries with tastings
- Typical Tuscan lunch
- Guided tour of a Tuscan village
- Tip: If you're a foodie, ask for pairing recommendations! Mill staff can often suggest specific dishes or recipes that highlight the best qualities of their olive oil.
- This experience is not accessible by wheelchair and pram/strollers.
- Safety is a priority so the wine tasting experience is restricted for guests under the age of 18 years.
- Guests under the age of 18 years can join the tour if they are each accompanied by at least one adult.
- Please inform of any food allergies or intolerances in advance. Vegetarian needs can also be accommodated if briefed in advance.
- You can cancel these tickets up to 24 hours before the experience begins and get a full refund.
- Kickstart your day with a scenic drive through the countryside aboard air-conditioned coaches that provide round-trip transfers from Florence to Pisa.
- On this exclusive 6-hour tour, discover the Romanesque architecture of distinctive Pisa with a knowledgeable tour guide.
- Enjoy free time to explore Piazza Dei Miracoli and its prized monuments on your own, one of which is the Cathedral.
- Kickstart your day with a scenic drive through the countryside aboard air-conditioned coaches that provide round-trip transfers from Florence to Pisa.
- On this exclusive 6-hour tour, discover the Romanesque architecture of distinctive Pisa with a knowledgeable tour guide.
- Enjoy free time to explore Piazza Dei Miracoli and its prized monuments on your own, one of which is the Cathedral.
Inclusions
- Staff assistance at the meeting point
- Round-trip transfers from Florence
- Air-conditioned coach with Wi-Fi onboard
- Licensed tour escort
- Free time to explore Pisa on your own (as per option selected)
- Guided walking tour of Pisa (as per option selected)
Exclusions
- Leaning Tower entry ticket
- Tip: During your free time, stroll across the many bridges across the great Arno River such as the Ponte Di Mezzo bridge, the most beautiful and prominent bridge in Pisa.
- Appropriate clothing is recommended while visiting places of worship.
- For small groups, up to 8 pax, the tour escort could be replaced by an English-speaking driver-guide.
- You can cancel these tickets up to 24 hours before the experience begins and get a full refund.
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4.5
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Carina
Aug 2024Verified booking
Giordano was a super friendly and motivated guide, who told us a lot about Pisa and Tuscany, and other places worth mentioning there, and also gave us special tips. The whole thing in fluent English, Spanish and also a little German :) Thanks also to bus driver Giovanni!
View original review in German
Angela
Aug 2024Verified booking
It was a very easy process to find our guide and get on the bus. They were very communicative and provided easy instructions. The bus to Pisa was nice and spacious and good AC. Our tour guide Ricardo once we arrived to Pisa was very knowledgeable, and had a great sense of humor. As expected, Pisa was a magical experience that my family will take forever. Great experience with Headout .
Cochet
May 2024Verified booking
Everything is beautiful! Dream day!!!😊 All of Florence is beautiful and Pisa is magical!!!
View original review in Spanish
Deepak
May 2024Verified booking
Pisa is a lovely place to see. The drive was awesome. The monuments are very well maintained.
Fernando
Nov 2024Verified booking
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FlorenceFlorence To Chianti Tours
Top things to do in Florence
Why go on a Chianti tour from Florence?
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Booking guide: Chianti tour from Florence
Experiences
Vineyard tour
Mode of transfer
Meals
Additional features
Tickets from
Siena, San Gimignano & Chianti Day Trip with Wine Tasting (11.5 hr.)
✅
AC Coach/Bus
❌
Free time in Siena and San Gimignano.
Siena, San Gimignano & Chianti Day Trip with Lunch & Wine Tasting (9 - 11 hr.)
✅
AC Coach
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Optional guided tour of Siena Catheral and Siena city center. Free time in San Gimignano.
Pisa, San Gimignano & Siena Day Trip with Lunch & Wine Tasting (12 hr. - 13 hr. 45 min.)
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AC Coach
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Free time in Pisa, lunch and wine tasting San Gimignano, optional guided tour of Siena Catheral and Siena city center.
Chianti Wine & Olive Oil Tasting Semi-Private Tour with Lunch (7 hr)
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Mercedes minibus or minivan
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Small group, guided tour of 1 olive oil mill, wineries and the Tuscan village.
Chianti Wine Making Experience with Gourmet Dinner (5 hr.)
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Mercedes minibus or minivan
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Wine-making experience, tasting of 5 different Tuscan wines and olive oil, one exclusive wine bottle with a personalized label.
Highlights of Chianti
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Other stops on your Florence to Chianti day trip
Siena
A medieval city rich in history, known for its stunning Piazza del Campo and the magnificent Siena Cathedral.
Don't miss: Climbing the Torre del Mangia for panoramic views of the city and countryside.
Siena tickets & tours
San Gimignano
This "Medieval Manhattan" is famous for its tall towers, cobblestone streets, and exceptional gelato.
Don't miss: Strolling through Piazza della Cisterna and tasting the award-winning gelato at Gelateria Dondoli.
San Gimignano tours
Pisa
Once a powerful maritime republic, Pisa is home to the iconic Leaning Tower, and known for its medieval architecture, particularly in the UNESCO-listed Piazza dei Miracoli, home to the cathedral and baptistery.
Don't miss: Taking a photo with the Leaning Tower, visiting the Piazza del Duomo, and exploring the nearby botanical gardens.
Pisa tickets & toursBest ways to reach Chianti from Florence
By train
By bus
By car
Best for: Scenic views of the countryside.
Duration: 1 hour 30 minutes
Closest train station: Poggibonsi and Castellina in Chianti.
Frequency: Every 30 minutes
Timings: 6am, with services continuing until evening.
- Take a train from Florence Santa Maria Novella station to Empoli. Change trains at Empoli for Poggibonsi or Castellina. The train routes don't actually cross through the Chianti region itself.
- From these stations, you can take local buses to reach different towns of Chianti like Greve or Castellina.
- Remember to validate your train ticket in the machines located at the station before boarding. This is required to avoid fines.
Best for: Budget travel and direct access to Chianti towns.
Duration: 1 hour
Closest bus station: Various stops in Chianti towns.
Frequency: Every hour.
Timings: 6:30am - 7pm
- Buses depart from Florence’s Santa Maria Novella train station or from Piazza della Stazione.
- The main bus line to Chianti is SITA, specifically Line 365. It connects Florence to various towns in Chianti, including Greve in Chianti, Radda in Chianti, and Castellina in Chianti.
- Buy tickets at local tabacchi (tobacco shops), at the bus station, or directly on the bus (with a small additional fee). Prices range from €3 to €5 depending on the destination. Do validate your ticket before boarding.
Best for: Flexibility and scenic exploration.
Duration: Approximately 30 to 45 minutes
Route options:
- Superstrada Firenze-Siena (SS67): This is a toll-free, four-lane highway that offers the fastest route to Chianti. It takes you along the western border of the region. Take the Poggibonsi Nord exit to enter Chianti.
- SR222 (Chiantigiana Road): This scenic two-lane road winds through the hills of Chianti, passing through picturesque villages and vineyards. This road can be narrow and winding, so drive carefully, especially when wildlife may cross the road at night.
- SR2 (Cassia): This historic Roman road runs parallel to the Superstrada and provides another route into Chianti, passing through towns like Poggibonsi and Monteriggioni.
Frequently asked questions about taking a Chianti tour from Florence
How far is Chianti from Florence?
The distance between Florence and the Chianti region is approximately 35 kilometers (21 miles) by road. It's a 45 minutes - 1 hour drive.
What’s the best way to get from Florence to Chianti—train, bus, car, or tour?
The best way to reach Chianti from Florence depends on your preferences. While buses and trains are budget-friendly, they require changing stops and aren't that flexible. Renting a car gives you freedom to explore but can be tricky with rural roads. Tours are the most convenient option, offering round-trip transfers, vineyard visits, and meals, letting you relax while everything is taken care of.
How early should I book a Chianti tour, especially during peak season?
It's recommended to book your Chianti tour at least two weeks in advance during peak season (June to August) to ensure availability, especially for popular tours that include wine tastings and visits to multiple towns. During other seasons, booking 3 days to one week in advance is fine.
Can I customize my Chianti tour?
While the core itinerary is standardized to ensure you experience the best of Chianti, we offer a variety of permutations and combinations to suit your preferences. You can choose from top experiences like visiting specific wineries, exploring historic towns such as Siena and San Gimignano, or even adding a traditional Tuscan lunch. This flexibility allows you to tailor your day while still benefiting from a well-planned tour.
Are the vineyard visits suitable for families with children?
The Chianti region is known for its laid-back, family-oriented culture, making it a comfortable environment for families to enjoy wine tasting and local cuisine together. Although, do note that guests under 18 must be accompanied by an adult to book our tours. Many wineries in Chianti are family-friendly, offering activities like scavenger hunts, outdoor play areas, and educational components about winemaking. It is generally recommended that children be at least 5 years old to enjoy the experience.
Do I need to know Italian to enjoy a Chianti tour?
Most Chianti tours are conducted in English, and guides are usually multilingual. However, knowing a few basic Italian phrases can enhance your experience, especially in smaller towns and local markets.
What should I expect in terms of wine tasting etiquette?
When attending a wine tasting, it's essential to follow some basic etiquette to enhance your experience and show respect for the hosts. Avoid wearing strong fragrances that can overpower the wine's aromas. Hold your glass by the stem to avoid warming the wine and leaving fingerprints. Take your time to savor each sip, and feel free to use a spittoon if you're tasting multiple wines. Engage with the pourer to learn more about the wines, and cleanse your palate between tastings. It's also perfectly fine to spit out wine to keep your palate fresh and avoid intoxication. Dress smart-casual, wear comfortable shoes, and keep an open mind to discover new flavors.