Florence · WINE TASTINGS IN CHIANTI

Wine Tasting in Chianti: The 15 Best Cellar Days

28 tours  ·  from $41

Two estates and lunch is the standard shape, three if the driver is quick. The 15 below are priced per head with the pours counted, and clear about which ones leave you free to buy a case at the gate.

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

1.Chianti Wineries Tour with Wine Tasting

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

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

2.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
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Florence: Pisa, Siena, S. Gimignano, Chianti Wine & Lunch

3.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

4.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

5.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
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Florence: S. Gimignano, Siena, Chianti & Wine Tasting Lunch

6.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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Half day Chianti Vineyard Escape from Florence with Wine Tastings - Cellars, vineyards, and the value of seeing production
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Half day Chianti Vineyard Escape from Florence with Wine Tastings

7.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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Tuscany Bike Tours Through the Chianti Hills with Wine Tasting - Getting fitted and ready to ride
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Tuscany Bike Tours Through the Chianti Hills with Wine Tasting

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

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

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

9.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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Chianti Wineries Tour with Tuscan Lunch and San Gimignano - The first Chianti winery: the personal side of wine
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Chianti Wineries Tour with Tuscan Lunch and San Gimignano

10.Chianti Wineries Tour with Tuscan Lunch and San Gimignano

★★★★★★★★★★5.0 · 793 reviews · 8 hours (approx.) · from $229

Spend eight hours with a small group visiting two Chianti wineries, tasting local wines, eating a Tuscan lunch, and exploring San Gimignano. Guides such as Daniel, Lorenzo, Christian, and Leonardo add history, humor, music, and practical help. Transport runs from central Florence.

“Absolutely 💯 a great day from start to finish!! Highly recommend this wine experience- top notch!! Started at a family run winery, visited a gorgeous small town and wandered through the streets then ended the tour at a stunning vineyard which included lunch.”

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From Florence: Chianti Wine Tour with Tasting - The first winery, a closer look at Tuscan production
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From Florence: Chianti Wine Tour with Tasting

11.Chianti Wine Tour with Tasting

★★★★★★★★★★4.5 · 729 reviews · 5.5 hours · from $41Best value

Ride from Florence into Chianti for two winery visits, cellar tours, and several wine tastings paired with cheese, meats, olive oil, and other Tuscan products. English-speaking guides such as Martina, Chiara, and Frederica lead the outing, which suits first-time wine visitors who want countryside views without spending a full day away.

“It was a great choice to do this tour! Frederica (our leader) and Ricardo (our driver) were great, true professionals, very helpful and pleasant. This is a great tour for anyone who wants a thorough introduction to Chianti wine.”

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From Florence: Chianti Hills Half-Day Tour with Wine Tasting - Meeting at Santa Maria Novella station
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From Florence: Chianti Hills Half-Day Tour with Wine Tasting

12.Chianti Hills Half-Day Tour with Wine Tasting

★★★★★★★★★★4.5 · 703 reviews · 5 hours · from $48

From Florence, ride an air-conditioned Gran Turismo bus into Chianti for vineyard walks, a vinegar cellar visit, seven wine tastings, Tuscan snacks and olive oils. Guides such as Chiara, Emma and Jordano add regional stories, while the half-day format suits busy itineraries.

“This was a well organized and fun half-day trip. Chiara, the tour guide, and the driver, Silvestro, were wonderful. The winery stop was lovely and welcoming. Nice wines and small bites of food to understand the pairings. Zero pressure to buy. Second stop in Radda was gorgeous and a fun tasting at a restaurant again with small bites. Recommend bringing snacks with you because there is little time to eat a meal.”

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Chianti Wine Tour from Florence with Tastings - Fattoria Lornano starts with wine and local food
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Chianti Wine Tour from Florence with Tastings

13.Chianti Wine Tour from Florence with Tastings

★★★★★★★★★★4.5 · 685 reviews · 5 hours 30 minutes (approx.) · from $42

Ride from Florence to two Tuscan wine estates for seven wine tastings, olive oil, balsamic vinegar, and local snacks. Guides such as Marco, Emma, and Marcus have led the tour, which ends with free time in medieval Monteriggioni. Expect a social group setting and limited time at each stop.

“Our trip was min. 30-40 minutes delayed because the first bus broke down and the second bus should have stayed in the garage . It was not safe to send us on a bus which was not able to make the trip. Otherwise the trip was very good.”

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Tuscany by Vespa Full-Day Tour to Chianti Wine Region - Cruising through Chianti at 20 kilometers per hour
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Tuscany by Vespa Full-Day Tour to Chianti Wine Region

14.Tuscany by Vespa Full-Day Tour to Chianti Wine Region

★★★★★★★★★★4.7 · 475 reviews

Ride a 50cc Piaggio Vespa from Florence into Chianti with an English-speaking guide such as Cecilia, Haider, Lorenzo, or Charlotte. Expect a safety briefing, quiet country roads, Greve and Impruneta stops, and a 17th-century villa meal with wine and olive oil tasting.

“We had an absolute great time on our tour! Our guides were knowledgeable and very friendly. It was awesome to cruise through the countryside with the wind in your hair! One suggestion is that they make a couple stops to take pics of the views. The only picture stop was on a road lined with cypress trees. It was very pretty but I wanted pics of the rolling hills and vineyards.”

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Chianti Delights: A Tale Of Two Wineries With A Vineyard Dinner - Into the Chianti hills
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Chianti Delights: A Tale Of Two Wineries With A Vineyard Dinner

15.Chianti Delights: A Tale Of Two Wineries With A Vineyard Dinner

★★★★★★★★★★4.0 · 324 reviews · 7 hours 30 minutes (approx.) · from $106

From Florence, ride to Siena for free time in Piazza del Campo, then visit Chianti wineries for tastings, olive oil, and a four-course Tuscan dinner. Guides such as Ana, Lisa, and Frederick have earned warm praise, but expect limited guided sightseeing and possible indoor dining.

“Stop in Siena was lovely however arrived at winery too late in pitch dark unable to see surrounding views, castle etc. Dinner is not really a 4 course made out to be in the brochure with cheese & meats to start, a basic Lasagna followed by sliced pork and potatoes. No vegetables or salad ( even on a share basis would be ok) Dessert was really disappointing....Biscotti biscuit only. Not really value for money unfortunately.”

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New in Wine Tastings in Chianti

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