WINE TOURS · FLORENCE WINE TOURS

Florence to the Vines: 15 Wine Tours Leaving the City

100 tours  ·  from $21 a head

Everything leaves from the same few streets and goes south. These 15 sort the Chianti afternoons from the full Tuscan days on price, pickup time and how many estates actually pour.

Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery - Siena Cathedral is worth the guided entry
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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

Spend 11 to 12 hours touring Tuscany by air-conditioned coach, with guided Siena and cathedral visits, free time in San Gimignano and Pisa, and a family-run winery lunch with four wine tastings. Guides such as Alex, Sara, Davide, and Manolo are known for clear directions, humor, and good pacing. Choose the Pisa tower upgrade if you want to climb.

“I had a fantastic experience with this tour guide Sara and Milano from start to finish. Everything was well-organized, smooth, and thoughtfully planned, which made the entire tour stress-free and enjoyable. Sara was knowledgeable, engaging, and passionate, sharing interesting facts and stories that really brought the place to life. Sara also very friendly, patient, and happy to answer all my questions. The pacing was perfect, and I never felt rushed, while still getting to see and learn so much. Overall, it was a truly memorable experience, and I am so glad I chose this operator. Highly recommended for anyone looking for a professional, informative, and enjoyable tour!”

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Florence: Pasta Cooking Class with Unlimited Wine - From flour to dough, the first hands-on lesson
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Florence: Pasta Cooking Class with Unlimited Wine

2.Pasta Cooking Class with Unlimited Wine

★★★★★★★★★★4.9 · 10,285 reviews · 3 hours · from $21Best value

Learn to make ravioli, tortelli, and pappardelle with chefs such as Andrea, Victoria, Antonio, and Valentino inside a 1200s medieval tower near Brunelleschi’s Dome. You prepare sauces, eat everything you cook, and enjoy Tuscan wine plus unlimited soft drinks during this three-hour English-language class.

“Fantastic ! Could not recommend enough. It’s fun, lively and really interesting. Super hands on the whole time - a really life way to dive into the food of Florence !”

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Florence: Chianti Wineries Tour with Wine Tasting - First winery: a close look at small-scale wine making
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Florence: Chianti Wineries Tour with Wine Tasting

3.Chianti Wineries Tour with Wine Tasting

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

Travel from Florence to two Chianti wineries in about five hours. Meet local producers, walk through vineyards, taste up to seven wines, and sample cheese, salami, bread, olive oil, and balsamic vinegar. Guides such as Ana, Alex, John, and Martina add regional stories along the way. Morning departures offer the best light for vineyard views.

“The tour was amazing, we had a great time with Ana, she is great and kind. We visited two wineries, but the first one, La Lama, was amazing. You will not regret this experience.”

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Small-Group Wine Tasting Experience in the Tuscan Countryside - Meeting near Santa Maria Novella
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Small-Group Wine Tasting Experience in the Tuscan Countryside

4.Small-Group Wine Tasting Experience in the Tuscan Countryside

★★★★★★★★★★5.0 · 7,392 reviews · 4 hours 45 minutes (approx.) · from $107

From Santa Maria Novella station, ride into Chianti with an English-speaking guide such as Leo, Jonathan, or Matteo. Visit two changing wineries, taste reds and olive oil, and enjoy cheese, salami, ham, and bruschetta at the second stop. This half-day outing runs about 4 hours 45 minutes and returns to Florence.

“Everything was wonderful! The guide was great and the transportation exceeded my expectations. Generous samplings of wine and food.”

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Florence: Pasta & Tiramisu Cooking Class with Unlimited Wine - Making fresh pasta from scratch
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Florence: Pasta & Tiramisu Cooking Class with Unlimited Wine

5.Pasta & Tiramisu Cooking Class with Unlimited Wine

★★★★★★★★★★4.9 · 6,708 reviews · 3 hours · from $56

Spend three hours in central Florence making fresh pasta and tiramisu with an English-speaking chef such as Amber, Alessandro, Clive, or Narghess. You will cook in a local restaurant, eat what you make, and enjoy wine with the meal, followed by limoncello or coffee. Recipes are provided to take home.

“This class with Amber was really great. She was immediately engaging and funny. Our small group all enjoyed music, wine, and a lot of laughs and learning. Amber taught us how to make pasta and tiramisu, gave us tips and recipes, and helped us to create a delicious dinner. After making our pasta, our group enjoyed wine and conversation in the restaurant while our pasta was cooked and sauced. We were amazed at how much and how amazing it all was. Thank you for such a fun and memorable experience, Amber! (We have already made tiramisu after returning home and can't wait to make some ravioli!)”

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Florence: Pasta Cooking Class with Unlimited Wine - From flour to dough, the first hands-on lesson
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Florence: Pasta Cooking Class with Unlimited Wine

6.Pasta Cooking Class with Unlimited Wine

★★★★★★★★★★5.0 · 6,413 reviews · 3 hours (approx.)

Meet your chef in a 1200s medieval tower near Brunelleschi’s Dome and learn to make ravioli, tortelli, and pappardelle from scratch. The chef prepares butter and sage, arrabbiata, and Tuscan ragù sauces while you work with the dough. Expect a lively English-language class for up to 15 people, followed by a generous pasta meal and Tuscan wine.

“We had Chef Valentino who was kind and educational. We had a great time, enjoyed all the flavors, and learned more about pasta making and sauce composition. I only wish there had been slightly more complexity to the course but given the time restraints the course content makes sense and was fun.”

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Pisa, Siena and San Gimignano Day Trip with Lunch & Wine Pairing - A Tuscan winery turns lunch into an attraction
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Pisa, Siena and San Gimignano Day Trip with Lunch & Wine Pairing

7.Pisa, Siena and San Gimignano Day Trip with Lunch & Wine Pairing

★★★★★★★★★★4.5 · 6,006 reviews · 12 hours (approx.) · from $78

Leave Florence at 7:30 a.m. for Siena, San Gimignano, and Pisa with an English-speaking tour escort. Choose guided Siena access and a winery lunch with Tuscan wine, then enjoy free time in the medieval towns. Expect a full 12 hours, a group of up to 63, and plenty of walking.

“Great tour, saw so much and the scenery just breathtaking. The bus was comfortable and the stops one better than the next. Highly recommend the tour.”

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SMALL-GROUP Wine Safaris: Tuscan Wine Tasting Tours from Florence - Leaving Florence in a custom 4x4
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SMALL-GROUP Wine Safaris: Tuscan Wine Tasting Tours from Florence

8.SMALL-GROUP Wine Safaris: Tuscan Wine Tasting Tours from Florence

★★★★★★★★★★5.0 · 5,088 reviews · 7 to 9 hours (approx.) · from $157

Leave Florence with an English-speaking sommelier and travel by air-conditioned 4x4 into Chianti or Val d’Orcia. Visit family-run wineries, historic cellars, and private vineyards, then enjoy wine, olive oil, salumi, cheese, and a Tuscan lunch or dinner. Guides such as Ginevra, Sara, Alex, and Fabio are known for making the day both informative and relaxed.

“Gloria and Roberto were amazing guides. Not only were the wineries diverse, but the knowledge shared was informative and interesting. Gloria also took the time to answer questions and ‘get to know the group’. Roberto was a smooth and careful driver.”

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Winner 2025 Florence Sunset Food & Wine Tour by Eating Europe - Charcuterie in a 12th-century cellar
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Winner 2025 Florence Sunset Food & Wine Tour by Eating Europe

9.Winner 2025 Florence Sunset Food & Wine Tour by Eating Europe

★★★★★★★★★★5.0 · 5,015 reviews · 3 hours 30 minutes (approx.) · from $149

Spend about three and a half hours eating and drinking through Florence’s Oltrarno district. You’ll taste Prosecco, four Tuscan wines, Pecorino, Parmigiano, gnudi, Tuscan soup, wild boar stew, gelato, and a Negroni. Guides such as Sara D., Antonella, Martino, Dimitri, and Caterina bring local food traditions and neighborhood stories to life.

“We had the best time and experience! Dimitri was excellent! He has very good explaining the history of the local area of Firenze and the cuisine of the people who live there. We enjoyed every place we went! Thanks Dimitri!!”

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From Florence: Siena, San Gimignano, Pisa & Lunch at Winery - Meeting the coach at Santa Maria Novella
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From Florence: Siena, San Gimignano, Pisa & Lunch at Winery

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

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

Spend 12 hours exploring Tuscany by comfortable coach, with a guided Siena walk, free time in San Gimignano and Pisa, and an optional farmhouse lunch at a Chianti winery. Guides such as Sara, Alessandro, and Giancarlo are known for lively storytelling. Choose the lunch option for wine tasting and countryside views, or skip it for more time in San Gimignano.

“Excellent trip, our guide Genevra was fabulous and our driver Giuseppe was fantastic. Would definitely recommend this trip.”

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San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch & Wine Tasting - Chianti wine and the midday meal
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San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch & Wine Tasting

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

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

Spend about 11 hours touring Tuscany by coach, with free time in San Gimignano and Monteriggioni, guided sights in Siena, and a winery lunch with three wines plus vin santo. Choose the Siena walking tour and cathedral option for added art and history. Guides may include Sandro, Marta, Alessandra, or Ilaria.

“Great experience with an opportunity to see a lot! My only recommendation would be that if you have the cathedral guided tour, have it start when you arrive in Sienna so you have a little bit more free time.”

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Florence: Pisa, Siena, S. Gimignano, Chianti Wine & Lunch - Pisa and the Field of Miracles in 80 minutes
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Florence: Pisa, Siena, S. Gimignano, Chianti Wine & Lunch

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

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

Travel from Florence to Pisa, San Gimignano, Chianti, and Siena on a 12-hour guided day trip. You’ll see Pisa’s cathedral complex, walk San Gimignano’s medieval streets, enjoy an optional Tuscan lunch with three wines and Vin Santo, and explore Siena with a guide. English and Spanish tours are available.

“The day trip was great! It was a great value for the money especially with the included lunch. Frederico was a great tour guide!”

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Chianti Wine Tour from Florence - The Via Chiantigiana makes the ride worthwhile
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Chianti Wine Tour from Florence

13.Chianti Wine Tour from Florence

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

Leave Florence by air-conditioned coach for two Chianti wineries along the Via Chiantigiana. Tour vineyards and cellars, taste six or seven Tuscan wines with local foods, and hear about winemaking from your guide and winery hosts. English and Spanish tours are available, with optional cooking class or lunch upgrades.

“The first winery was just okay but the second was really nice because of the property. The hosts were fun.”

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From Florence: Small Group Wine Tasting Tour to Tuscany - Meeting at Piazzale Montelungo
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From Florence: Small Group Wine Tasting Tour to Tuscany

14.Small Group Wine Tasting Tour to Tuscany

★★★★★★★★★★4.9 · 3,902 reviews · 4.5 hours · from $105

Leave Florence by air-conditioned minibus for two Chianti Classico estates. Taste about six wines, fresh olive oils, pecorino, salami, cold cuts, and bruschetta while learning how each winery works. Guides such as Jason, Jonathan, Leo, and Rafael are known for lively commentary, though the exact guide and wineries can vary.

“This was the most fun day, and I highly recommend this to anyone traveling to the Tuscany area. Raffaele was the best guide, full of energy and humor and great tips on the wine and food scene in Florence. Our group was fantastic and the wineries were beautiful!”

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Florence: S. Gimignano, Siena, Chianti Wine Tasting & Lunch - Lunch, wine, and the Chianti hills
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Florence: S. Gimignano, Siena, Chianti Wine Tasting & Lunch

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

★★★★★★★★★★4.6 · 3,102 reviews · 11 hours · from $82

Spend a full day beyond Florence with guides such as Ricardo, Marta, or Sandro, depending on the departure. Explore San Gimignano and Siena, visit Monteriggioni in season, and stop at a Chianti winery for a cellar visit, three-course Tuscan lunch, and tasting of three wines plus Vin Santo. Choose the Siena walking tour and cathedral visit for more guided context.

“Riccardo, Scirin and colleagues were fantastic hosts. Very knowledgeable and funny and full of interesting facts Also the organisation was superb in terms of pick up , ensuring we knew where to go and when to get picked up Nice meal and wine tasting was a bonus”

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