Florence · CHIANTI TOURS

The 15 Best Chianti Tours from Florence

45 tours  ·  from $41

The hills start half an hour south and the roads through them are the point. These 15 sort the wine days from the Vespa runs, the e-bike routes and the hikes, on price, how many estates you actually get inside, and whether lunch is included.

Florence: Pisa, Siena, San Gimignano, and Chianti Experience - Meeting in Florence and settling into the coach
Chianti Tours, Pisa and Lucca Day Trips, Siena and San Gimignano Day Trips, Tour Reviews

Florence: Pisa, Siena, San Gimignano, and Chianti Experience

1.Pisa, Siena, San Gimignano, and Chianti Experience

★★★★★★★★★★4.5 · 8,393 reviews · 12 hours · from $52Our pick

Travel from Florence to Pisa, San Gimignano, Siena, and the Chianti Hills in 12 hours. You get free time in each town, with optional Leaning Tower tickets, a Siena walking tour, and a winery lunch with tasting. Guides such as Barbara and Anna add useful local tips along the way.

“Our guide Hillary was very knowledgable and provided excellent explanations of the places that we visited including their history and some curiosities as well as some recommendations of places to visit and traditional food to taste. The tour was very well organised and allow us to have a good insight into the region. Our bus driver Salvatore was also really nice and we appreciate his contribution to the success of the tour. I would recommend this tour to anyone visiting Firenze.”

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Florence: Chianti Wineries Tour with Wine Tasting - Meeting at Piazzale Montelungo
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Florence: Chianti Wineries Tour with Wine Tasting

2.Chianti Wineries Tour with Wine Tasting

★★★★★★★★★★4.5 · 8,301 reviews · from $56

Travel by comfortable coach from Florence to two Chianti wineries for guided tours, vineyard walks, and tastings of up to seven wines. Guides such as Martina, Cecilia, Giulia, and John have led recent departures, while local producers explain wine, food, and Tuscan traditions.

“Great experience! Our guide Constantino and driver Ricardo were both fantastic. Both wineries were a good experience and had delicious wines”

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San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch & Wine Tasting - San Gimignano and its forest of towers
1-Day Tours, Chianti Tours, Florence Day Trips, Florence Wine Tastings, Food & Drink, Lunch Experiences, Siena and San Gimignano Day Trips, Tour Reviews, Wine Tastings in Chianti, Wine Tours

San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch & Wine Tasting

3.San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch & Wine Tasting

★★★★★★★★★★4.5 · 4,432 reviews · 11 hours (approx.) · from $83

Leave Florence by coach for San Gimignano’s towers, Monteriggioni’s medieval walls, a Chianti winery lunch with three wines, and Siena’s cathedral and Campo. Choose between free exploration and added Siena guiding. Expect hills, uneven streets, and a full 11-hour day.

“We have been to Italy many times and have been on dozens of tours. This tour was - by far - the worst tour ever. There were 75-80 people on our tour. Who would ever sign up for a tour, anywhere, with that many people? We were loaded onto a double decker bus and the tour company paired our English speaking tour with a Spanish speaking tour. Every discussion/announcement was in 2 languages. Moving that many people from one location to the next was an effort and took away from the time that could have been spent in any of the location stops. One of the worst parts of the…”

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Florence: Pisa, Siena, S. Gimignano, Chianti Wine & Lunch - Starting at Piazzale Montelungo
Chianti Tours, Florence Wine Tastings, Lunch Experiences, Pisa and Lucca Day Trips, Siena and San Gimignano Day Trips, Tour Reviews, Wine Tastings in Chianti, Wine Tours

Florence: Pisa, Siena, S. Gimignano, Chianti Wine & Lunch

4.Pisa, Siena, S. Gimignano, Chianti Wine & Lunch

★★★★★★★★★★4.6 · 4,354 reviews · 12 hours · from $77

This 12-hour coach tour links Pisa, San Gimignano, Chianti, and Siena from Florence. Expect a busy but well-planned day, English or Spanish guidance, Siena touring options, and a three-course Tuscan lunch with three wines and Vin Santo if selected.

“We had an excellent trip, thanks to our fabulous guides. The bus was easy to access, and the time spent at each location was perfectly spaced.”

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Chianti Wine Tour from Florence - First Winery: A Small Organic Producer
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Chianti Wine Tour from Florence

5.Chianti Wine Tour from Florence

★★★★★★★★★★4.5 · 3,979 reviews · 5 hours (approx.) · from $59

Leave Florence by air-conditioned coach for two organic Chianti wineries. You will taste six or seven Tuscan wines, bruschetta, cheese, salami, olive oil, and balsamic vinegar, with vineyard and cellar visits led by local producers. Guides such as Aaron, Alessandra, or Cristina may lead the English tour.

“Both wineries were amazing! Lots of Knowledge about making the wine and very personal wanted you to ask questions and just talked to you during the tour. Tommas from the second location super friendly and did an excellent job! Both shipped to the US and you could buy another glass while you walked around the site. Both had some snacks at the venues, but would eat lunch or dinner before going.”

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Siena, San Gimignano and Chianti Wines Day Tour from Florence - A short hour in San Gimignano
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Siena, San Gimignano and Chianti Wines Day Tour from Florence

6.Siena, San Gimignano and Chianti Wines Day Tour from Florence

★★★★★★★★★★4.5 · 2,542 reviews · 10 hours 30 minutes (approx.) · from $78

Spend about 10.5 hours exploring three Tuscan towns from Florence by air-conditioned coach. See Siena’s Piazza del Campo and Duomo, wander San Gimignano, stop at Monteriggioni, and taste two or three Chianti wines with regional snacks. Choose guided Siena sightseeing or more free time.

“Ronaldo and Roberto did a great job of getting us to our destinations and communicating things to do at each stop. This tour is a large group tour on a coach bus. We still kept to our schedule. Siena is beautiful along with the other stops. The only thing i wish were different was the order of the stops. It was close to dark when we arrived to San Gimignano and would have preferred to be in Siena in the evening. Thanks for conducting the tour, so we could see more on our Italy trip!”

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Florence: S. Gimignano, Siena, Chianti & Wine Tasting Lunch - San Gimignano and its famous towers
Chianti Tours, Florence Wine Tastings, Food & Drink, Lunch Experiences, Siena and San Gimignano Day Trips, Tour Reviews, Wine Tastings in Chianti, Wine Tours

Florence: S. Gimignano, Siena, Chianti & Wine Tasting Lunch

7.S. Gimignano, Siena, Chianti & Wine Tasting Lunch

★★★★★★★★★★4.6 · 2,427 reviews · from $89

Travel from Florence by air-conditioned coach to San Gimignano, Monteriggioni, Siena, and a Chianti winery. You get free time in the hill towns, a three-course lunch, three-wine tasting, and optional Siena Cathedral access. Guides such as Aaron, Marta, and Ricardo have led recent departures.

“We had ample time in each location, as well as recommendations from the guide on what to do. The wine tasting & lunch were fantastic, would highly highly recommend, both delicious and engaging! Illaria was an excellent guide!”

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From Florence: Chianti Half-Day Afternoon Tour - The Bus Ride Into the Chianti Hills
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From Florence: Chianti Half-Day Afternoon Tour

8.Chianti Half-Day Afternoon Tour

★★★★★★★★★★4.4 · 2,328 reviews · from $55

Spend an afternoon in Chianti with an English-speaking host, two winery visits, seven wine tastings, olive oil, balsamic vinegar, salami, and Tuscan bread. You will also have time to stroll through Monteriggioni. Guides have included Marta, Andrea, Marco, and Maria.

“Excellent trip exactly as described. Marco was a great guide”

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Tuscany: Day Trip to Pisa, Siena, San Gimignano, and Chianti - Siena and the Piazza del Campo
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Tuscany: Day Trip to Pisa, Siena, San Gimignano, and Chianti

9.Day Trip to Pisa, Siena, San Gimignano, and Chianti

★★★★★★★★★★5.0 · 2,283 reviews · 12 hours (approx.) · from $78Top rated

Leave Florence at 7:30 am for a full-day bus tour through Tuscany. Walk Siena with a local guide, visit its cathedral if selected, eat at a family-run winery, explore San Gimignano, and see Pisa’s famous square and Leaning Tower. English service, with some departures combining languages.

“Whilst this is a long day, it was worth it to see all the sights we saw! Our favourite stop was Siena, we would have loved to spend more time there. Lunch at Sam Gimignano was really nice. Our guide at Siena was quite difficult to understand and very breathy, she was struggling with the inclines. It was good to understand the history but also lovely to walk around on our own.”

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Half day Chianti Vineyard Escape from Florence with Wine Tastings - Cellars, vineyards, and the value of seeing production
Chianti Tours, Florence Wine Tastings, Tour Reviews, Wine Tastings in Chianti, Wine Tours

Half day Chianti Vineyard Escape from Florence with Wine Tastings

10.Half day Chianti Vineyard Escape from Florence with Wine Tastings

★★★★★★★★★★4.5 · 2,196 reviews · 5 hours (approx.) · from $53

Leave Florence by Wi-Fi-equipped coach with an English-speaking guide, such as Alex or Lorenza, for two Chianti estates. Taste three to four wines at each, sample olive oil, cheese, and balsamic vinegar, visit cellars, and return after about five hours.

“Everything about this excursion was great! Fantastic communication leading up to it. Both wineries were awesome in their own way. The first was more of a small family business while the second seemed a little "classier." Great views at both. Comfy ride. If you're looking for an escape from the city, I highly recommend!”

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Chianti Vespa Tour with Lunch from Florence & E-car Option - The practice course and the safety test
Chianti Tours, Florence Vespa and Fiat 500 Tours, Lunch Experiences, Tour Reviews, Tours, Vespa and Fiat 500 Tours in Chianti

Chianti Vespa Tour with Lunch from Florence & E-car Option

11.Chianti Vespa Tour with Lunch from Florence & E-car Option

★★★★★★★★★★5.0 · 1,453 reviews · 6 hours 30 minutes (approx.) · from $125

Leave Florence by minivan for Chianti, then ride a classic Vespa or Fiat Topolino through vineyard roads with guides such as Yo, Julia, Haider, and Lorenzo. Expect a safety test, photo stops, winery visits, wine and olive oil tastings, and a Tuscan lunch.

“This was a 10/10 experience! The guides were so informative and personable, which made the trip even better. The only guide we recall is Haider, but there was a female guide as well but we did not catch her name. You take a bus to a parking lot to get you out of the city and familiar with the vespas prior to taking them out on the road. We appreciated the professionalism from the guides as they will make sure anyone who is driving is competent with the vespas to ensure everyone is safe. Then, you hit the road and get to spend a good amount of time to drive…”

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Tuscany Bike Tours Through the Chianti Hills with Wine Tasting - Getting fitted and ready to ride
Bike and E-Bike Tours in Chianti, Chianti Tours, Cycling Tours, Florence Bike and E-Bike Tours, Florence Wine Tastings, Food & Drink, Tour Reviews, Tours, Wine Tastings in Chianti, Wine Tours

Tuscany Bike Tours Through the Chianti Hills with Wine Tasting

12.Tuscany Bike Tours Through the Chianti Hills with Wine Tasting

★★★★★★★★★★5.0 · 1,300 reviews · 6 hours (approx.) · from $145

Leave Florence by van for a roughly 12-mile ride through Chianti’s vineyards and olive groves. Guides such as Ben, Filippo, Angus, and Alessio lead the route, with photo stops, a castle wine tasting, olive oil, and a Tuscan lunch. E-bikes cost extra.

“This was the BEST tour by far! The guides, Ben & Angus were friendly, personable, & knowledgeable. The bike ride was awesome and the wine spectacular. This is a must if you want out of the city to explore Tuscany and be active.”

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Essence of Chianti Small Group Tour with Lunch and Tastings from Florence - Tenuta Riseccoli, an organic family winery on the hill
Chianti Tours, Lunch Experiences, Tour Reviews, Tours

Essence of Chianti Small Group Tour with Lunch and Tastings from Florence

13.Essence of Chianti Small Group Tour with Lunch and Tastings from Florence

★★★★★★★★★★5.0 · 1,269 reviews · 8 hours (approx.) · from $180

Leave Florence at 9 a.m. for three Chianti wineries, a stop in Greve, olive oil tastings, and a Tuscan lunch. Guides such as Alessio, Leo, Jason, Valentina, and Leonardo bring history and humor to the day. Expect an air-conditioned ride, a group of up to 25, and a return around 5 p.m.

“It is wonderful. My wife and I do not usually enjoy group tours however this one was highly recommended by a friend. Each winery offered a little different experience. Our guide, Angie, and driver, Alex made the trip so much fun. One thing to keep in mind is that there is no restroom on the bus and also no food or drink other than water. The tour was capped at 25 people which allowed us to meet and socialize with people from all over the world. My wife has a milk allergy and each snack and lunch was prepared without dairy.”

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From Florence: Chianti Wine Tour with Tastings - The Drive Across Sienese Chianti
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From Florence: Chianti Wine Tour with Tastings

14.Chianti Wine Tour with Tastings

★★★★★★★★★★4.4 · 1,025 reviews · from $62

Spend five hours in Chianti with an English or Spanish-speaking guide, visiting two organic wineries. Walk through vineyards and old cellars, taste three to four wines at each stop, and sample pecorino and other Tuscan products. Guides may include Aaron, Alessia, Vera, Keiko, or Mario.

“It was lovely! Lots of great wine and informative speakers with breadth of knowledge. Cruisey drive as well!”

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From Florence: Private Chianti Hills Tour with Tasting - Radda in Chianti: a short walk through the village
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From Florence: Private Chianti Hills Tour with Tasting

15.Private Chianti Hills Tour with Tasting

★★★★★★★★★★4.3 · 809 reviews · 6 hours

Spend six hours in Chianti with a private-group guide, two winery stops, six local wines, Tuscan food pairings, and free time in Radda. Guides such as Anna, Chiara, Abbie, and Rosa have earned praise for their warmth and local insight, while drivers handle the region’s narrow, winding roads.

“Everything was super great! The trip, the wine, the wineries, the driver…was my amazing experience in Florence! End Chiara, the guide is wonderful and amazing women! ❤️ I spend a great time and I have more informations plus. Many thanks to all! A real pleasure!”

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