The 15 Best Wine Tours from Florence

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Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery

1.Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery

★★★★★★★★★★5.0 · 21,634 reviews · 11 to 12 hours (approx.) · from $114Our pick

Travel by air-conditioned coach from Florence to Siena, San Gimignano, Pisa, and a Chianti winery. You’ll tour Siena Cathedral, enjoy free time in three towns, and can add a farmhouse lunch with four wine tastings and a Leaning Tower climb.

“We went on this day trip during our honeymoon in October 2025. This excursion was an outstanding experience thanks to our tour guide, Giancarlo. He was engaging, informative, funny, and knowledgeable. Siena, San Gimignano, Pisa, and lunch at the winery were beautiful. It is a long day so be sure to dress comfortably. This day trip was one of the highlights of our trip. We highly recommend going on this tour.”

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Florence: Chianti Wineries Tour with Wine Tasting

2.Chianti Wineries Tour with Wine Tasting

★★★★★★★★★★4.5 · 10,071 reviews · 5 - 5.5 hours · from $41Best value

Travel from Florence to two Chianti wineries by comfortable GT bus, meet local producers, walk through vineyards, and taste three to four wines at each stop. Guides such as Ana, Alex, Martina, and John add local context, while cheese, salami, olive oil, bread, and balsamic vinegar round out the tastings.

“Both wineries were beautiful and had excellent tastings. Both also offered the option to ship wines if you decided to purchase any. Emma and the driver (sorry I forgot his name) made the trip fun and informative. Both of them handled traffic well and kept us on schedule.”

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From Florence: Siena, San Gimignano, Pisa & Lunch at Winery

3.Siena, San Gimignano, Pisa & Lunch at Winery

★★★★★★★★★★4.8 · 4,538 reviews · 12 hours · from $112

Join guides such as Sara, Alessandro, or Giancarlo for a full day through Tuscany. Walk Siena’s medieval center, taste four wines over a farmhouse lunch in Chianti, explore San Gimignano, and finish beside Pisa’s Leaning Tower. Choose the lunch and tower-entry options carefully.

“The pace was perfect. We were able to see a variety of the cities and countryside, without rushing. Our guide, Gabriel, did a great job and our driver, Domenico, was fantastic as well. Lunch was pasta, and some appetizers, which were tasty. Will recommend to all our friends!”

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Half day Chianti Vineyard Escape from Florence with Wine Tastings

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

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

Ride from Florence to two Chianti estates with an English-speaking guide, taste three to four wines at each, sample olive oil, cheese, and balsamic vinegar, and tour vineyards and cellars. Guides such as Alex, Lorenza, and Cecilia have led especially engaging outings, though groups can reach 43 people.

“We had a great time. Our tour guide Cecilia, was charming and informative. The two wineries were different from each other, so it was interesting. Great driver too.”

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Tuscany Wine Tour: 2 Wineries & San Gimignano from Florence

5.Tuscany Wine Tour: 2 Wineries & San Gimignano from Florence

★★★★★★★★★★5.0 · 1,007 reviews · 7 hours (approx.) · from $229

Leave Florence at 10am for two winery visits, guided tastings of Chianti, Vernaccia, rosé, and more, plus olive oil and balsamic pairings. Your guide drives the scenic Chianti Road, then gives you 90 minutes to explore San Gimignano before returning around 5pm.

“The communication, and experience as a whole was excellent. Emanuele was superb and the two different wine experiences made it even more enjoyable. The views, amazing and finishing off at San Gimignano was a delight being able to have some free time to venture out.”

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From Florence: Private Chianti Hills Tour with Tasting

6.Private Chianti Hills Tour with Tasting

★★★★★★★★★★4.3 · 809 reviews · 6 hours

Spend six hours in Chianti with a guide and minivan, stopping at two wineries and a wine shop in Radda. Taste six local wines with olive oil, cheeses, bread, and cured meats, then stroll Radda’s lanes. Hotel pickup may be requested in central Florence.

“It was fantastic. We had a great time. The wine were great, the views, Marina and Luigi... Overall a wonderful time discovering Chianti and its wine.”

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Chianti Wineries Tour with Tuscan Lunch and San Gimignano

7.Chianti Wineries Tour with Tuscan Lunch and San Gimignano

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

Spend about eight hours visiting two Chianti wineries, tasting local wines, sharing a Tuscan lunch, and exploring San Gimignano. Guides such as Lorenzo, Daniel, Christian, and Cecilia are praised for their warmth and local stories, while the group size is capped at 16.

“Tour was excellent! Daniel the tour guide was the best, he explained everything, took pictures, played great car music & so polite. Wineries were amazing, breads, cheeses, meats, vegetables & the best pasta we ever ate, so much delicious wine & food.”

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Private Self-Guided E-Bike Ride in Tuscany with Vineyard Visit

8.Private Self-Guided E-Bike Ride in Tuscany with Vineyard Visit

★★★★★★★★★★5.0 · 775 reviews · 4 to 7 hours (approx.) · from $96

Set out from central Florence with John’s e-bike team, then follow a GPS route through Fiesole, olive groves, forest roads, and Tuscan hills to a boutique vineyard. Wine, food, and tastings cost extra. You ride independently, so solid bike skills and comfort with traffic are essential.

“This was brilliant. Easy to follow and exceptionally beautiful route. The bikes give as mush assistance as you want and worked well. Lovely accommodating host who gives a great explanation of everything to expect on bike ride.”

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Florence: Chianti Wine Region Vespa or Fiat Topolino Tour

9.Chianti Wine Region Vespa or Fiat Topolino Tour

★★★★★★★★★★4.8 · 739 reviews · 6 - 6.5 hours

Join an English-speaking guide such as Niccolo, Julia, Yo, or Heather for a 6 to 6.5-hour Chianti outing from Florence. Ride a 50cc Vespa on quiet paved roads, or choose the electric Fiat Topolino. Stop in medieval villages, visit a winery, and enjoy lunch with wine and olive oil.

“Overall, the experience was great! Riding the vespa around the countryside was great! Yhe sightseeing was absolutely incredible! The tour guides were helpful with teaching you how to safely ride the vespa, and kept you safe on the road by having one guide in the front of the pack and another at the back. You got to ride the vespa long enough to really enjoy the experience. It was also really nice being able to have a little free time in Greve to shop around and enjoy a little break! That was an unexpected surprise! The wine tasting olive oil tasting and lunch was really nice! The lunch was simple,…”

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Tuscany Wine Tour : 2 Wineries & San Gimignano from Florence

10.Tuscany Wine Tour : 2 Wineries & San Gimignano from Florence

★★★★★★★★★★4.8 · 594 reviews · 7 hours · from $201

Leave Florence at 10:00 for two contrasting Chianti wineries, tasting up to seven wines, olive oil, balsamic, and local foods. Your English-speaking guide, perhaps Dom, Valentina, or Alessandro, handles the roads while you enjoy the countryside and 1.5 hours in San Gimignano.

“The stop at Tenuto Torciano winery was the highlight of the trip. The experience was excellent as we're the wines. we bought four bottles to enjoy back at home.”

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

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

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

Leave Florence at 2:45 pm for Siena and the Chianti hills. You’ll have free time in Siena, visit wine estates, taste Tuscan wines and olive oil, and enjoy a four-course dinner. Guides such as Ana, Lisa, Frederick, Diego, and Marti have led departures, though the exact guide varies.

“Very disappointed with the tour. Maybe I should have booked a different one. The tour guide was very nice, but didn’t have to do much. She led us from the bus into Siena, and then told us to meet back in 2 hours. The wine experience was poor at best. The staff showed a total lack of interest - didn’t walk us thru the meals and wine. Very little commentary from them. They missed a great opportunity as their place is beautiful. But the execution was awful. I’ve had great luck with Viator but this one was clearly the worst.”

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Chianti Vineyards Escape from Florence with Two Wine Tastings

12.Chianti Vineyards Escape from Florence with Two Wine Tastings

★★★★★★★★★★4.5 · 280 reviews · 5 hours (approx.) · from $53

Leave Florence by coach for two Chianti estates, where you’ll tour cellars, see vineyards and olive groves, and taste several wines with cheese, salami, olive oil, and balsamic vinegar. Guides such as Anna, Emma, and Margherita have added warmth and useful local tips, but the group can reach 43 people.

“We liked that round-trip transportation was included in the cost. We visited two wineries for about 30-40 min each. We enjoyed Il Molino de Grace. The views at Riseccoli were nice and rustic, but we didn't like their wines very much for various reasons but mostly because the flavors were off - didn't think the grapes they used blended well together. I would say this was an efficient wine tasting with a brief opportunity to take photos. Lunch was not included. If you're looking for a slow-paced, relaxed winery visit it would probably be best to try a full day tour. Anna was our guide and she was very engaging…”

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From Florence: Small Group Vespa Tour Tuscany Winery & Lunch

13.Small Group Vespa Tour Tuscany Winery & Lunch

★★★★★★★★★★4.9 · 268 reviews · 7 hours · from $235

Spend seven hours with FunInTuscany riding quiet Chianti roads, visiting San Gimignano, and sharing lunch and wine at a local winery. Guides including Lorenzo, Daniel, Cecilia, and Mido help beginners feel safe, while non-riders can travel with a guide or in a Tuk-Tuk.

“Such a fun day! Our guide was great fun and very knowledgeable. I felt safe during the whole trip. The day ended with a superb L nah and wine tasting. Thoroughly enjoyable and would definitely recommend”

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Super Chianti 2 wineries & meat feast @ Dario Cecchini—max 8 pp

14.Super Chianti 2 wineries & meat feast @ Dario Cecchini—max 8 pp

★★★★★★★★★★5.0 · 258 reviews · 7 hours (approx.) · from $332

Travel from Florence in a group of no more than eight for visits to two active Chianti wineries, about 10 wine samples, and lunch at Dario Cecchini’s famous butcher shop. Guides such as Matteo, Quentin, and Clemente bring wine, food, and Tuscan culture to life.

“I have done many wine tours- most amazing but this topped them! Matteo’s passion and level of expertise is unmatched- I learned so much about how climate soil wine maker are interwoven with culture food and history and create an atmosphere that influences taste and experience. Knowing Dario’s advocacy and life story elevated our meal and quite frankly I was star struck . The van was comfortable and we bonded immediately not only with Mateo who asked us a few questions at the start that were ice breakers for our small group of 5 to connect- clever!!! The vineyards were local small owners not large producers and the cheese also…”

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Florence: Chianti Vineyards Tour with Wine Tasting & Dinner

15.Chianti Vineyards Tour with Wine Tasting & Dinner

★★★★★★★★★★4.1 · 226 reviews · 8 hours · from $128

Travel from Florence by air-conditioned minivan or coach to a Tuscan wine estate. Tour the winery, taste local wines and farm products, then share a candlelit dinner among the vines. Hosts such as Aurora, Marta, and Luca add local stories, while bad-weather dinners move indoors.

“Had a wonderful evening. Tour included a short stop in a beautiful town before heading to the winery. Lovely dinner in outside at a beautifully set table with a tasting of wine with each course.”

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