Florence · FLORENCE WINE TOURS

Wine Tours from Florence: 15 Tastings in the Tuscan Hills

100 tours  ·  from $15 a head

Chianti starts twenty minutes south of the city, and Montalcino is an easy day further. These 15 tastings and vineyard days are compared on price, how many wines you pour and whether lunch comes with them.

Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery - A Chianti farmhouse lunch worth lingering over
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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

Leave Florence by air-conditioned coach for Siena, where a local guide leads you through the medieval center and into its cathedral. Then visit a Chianti farmhouse for lunch and four wine tastings, followed by free time in San Gimignano and Pisa. The day runs about 11 to 12 hours; climbing the Leaning Tower requires a separate ticket upgrade.

“We had an absolutely incredible day with David as our guide! From the moment we met him, he made us feel so welcomed and at home, creating such a warm and fun atmosphere throughout the entire experience. Even with the rain, we truly enjoyed every stop! Siena, San Gimignano, the incredibly winery, and Pisa. Each place was breathtaking and made for an unforgettable day. The food and the wine were an absolute cherry on top! Chefs kiss Our small group was amazing, and we loved meeting people from all over the world who now feel like new friends. I would 100% recommend this tour to anyone, and I would happily…”

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Florence: Pasta Cooking Class with Unlimited Wine - Sauces make the pasta lesson a meal
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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

Make ravioli, tortelli, and pappardelle from scratch in a medieval tower near Brunelleschi’s Dome. A chef, including instructors such as Andrea, Antonio, and Victoria, guides each step, from dough to sauces. You eat what the group prepares, with Tuscan wine and soft drinks included.

“Awesome experience. Antonio was a great guide and chef!”

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Florence: Chianti Wineries Tour with Wine Tasting - Between stops: a short ride and another view of the region
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Florence: Chianti Wineries Tour with Wine Tasting

3.Chianti Wineries Tour with Wine Tasting

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

Ride from Florence to two Chianti wineries for vineyard walks, winemaking introductions, and tastings of up to seven wines in all. Your English-speaking tour leader shares local context en route; winery hosts explain their wines and serve Tuscan snacks. Expect about 5.5 hours away, with coach transport and no lunch included.

“Such an incredible time! Cecilia was our guide and did a wonderful job. The host at the first winery was also incredibly knowledgeable and exciting when telling us about the wine and history. Highly recommend!”

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Small-Group Wine Tasting Experience in the Tuscan Countryside - Second stop: another estate and local food
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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

Ride from Florence into the Chianti hills for visits to two wine estates, with vineyard and cellar tours, tastings of local reds and olive oil, and Tuscan snacks at the second stop. Guides such as Matteo, Leo, and Jonathan have led the trip, though the assigned guide and wineries can vary.

“We had the best time with Leo, the 2 wineries we stopped at were unbelievable. Bonus, you get to meet so many amazing people on the journey!”

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Florence: Pasta & Tiramisu Cooking Class with Unlimited Wine - Tiramisu is part of the lesson
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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 a restaurant in central Florence making fresh pasta from scratch and preparing tiramisu with an English-speaking instructor. Then eat what you made with wine, and finish with limoncello or coffee. Instructors have included Amber, Alessandro, Clive, Narghess, and Alexandrea. The $56 price includes the class, meal, dessert, and wine.

“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 - Sauces make the pasta lesson a meal
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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.)

In central Florence, a chef guides you through fresh ravioli, tortelli and pappardelle in a 13th-century tower linked to Dante’s wife’s family. The three-hour English-language class provides ingredients and equipment, then serves your pasta with Tuscan sauces, wine and soft drinks. Classes are capped at 15; instructors have included Lorenzo, Antonio and Valentino.

“It was really fun! Really great experience and would highly recommend:) got to make three different types of pasta and try them with different sauces”

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Pisa, Siena and San Gimignano Day Trip with Lunch & Wine Pairing - Siena: Piazza del Campo and the cathedral square
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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 am by air-conditioned coach for Siena, San Gimignano and Pisa. Depending on your selected option, you’ll have a local guide in Siena and a three-course winery lunch with wine pairing. Expect a full 12-hour day, free time in each town and plenty of walking.

“You get a great overview of many places in a single day. There is not a lot of time for in depth sightseeing but you get to many places. They pull it off flawlessly.”

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SMALL-GROUP Wine Safaris: Tuscan Wine Tasting Tours from Florence - What the tastings and meal add
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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 central Florence in an air-conditioned 4x4 for a guided wine day in Chianti or Val d’Orcia. Choose a daytime or sunset route, with stops at family-owned wineries, wine and olive oil tastings, and a Tuscan meal. Guides including Sara, Alex, and Ginevra have led tours, though your guide may vary.

“Such an amazing time with Ginevra and Christophe. Ginevera made the tour interesting and educational while keeping it fun and light. I learned a ton about the region, the different wines and loved the guided wine tasting practice. Wine was delicious (especially the Zac) and the food included was lovely. Christophe took good care to keep us safe on our drive while adding a bit of excitement along the way. Great experience.”

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Winner 2025 Florence Sunset Food & Wine Tour by Eating Europe - Negroni and cucina povera through a wine window
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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 walking Florence’s Oltrarno with an English-speaking guide and a group of no more than 13. Taste Tuscan wines, sample local cheeses and dishes, learn the story of the city’s wine windows, and finish with artisan gelato. Guide names have included Antonella, Martino, Dimitri, Sara D. and Ellie, but your assigned guide may vary.

“Sara Giovanna was an amazing tour guide. She took us all over Florence and we ate so much yummy food and learned a lot about florentine cooking. We would definitely recommend.”

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From Florence: Siena, San Gimignano, Pisa & Lunch at Winery - Lunch among the Chianti vines
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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

Travel by air-conditioned coach from Florence to Siena, a Chianti winery, San Gimignano and Pisa. A local guide leads the Siena walk, while you have free time at the other stops. Choose the farmhouse lunch and four-wine tasting, and check your option carefully if you want a Leaning Tower ticket. Guides vary, with Sara, Alessandro and Manolo among those who lead departures.

“It was great and perfect. Tour guide was super good, fun and friendly. Making everyone feel welcome and the tour enjoyable! 1000% to join this tour!”

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San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch & Wine Tasting - San Gimignano: towers, lanes, and a short window
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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

Leave Florence by coach for San Gimignano, Monteriggioni (April to October), a Chianti winery lunch and tasting, and Siena. Expect free time in the towns, with a Siena walking tour and cathedral entry available only on selected options. Guide teams vary; past departures have included Sandro, Ricardo, Marta and Ilaria.

“Other reviews are correct- this is not a guided tour. However, I liked how we are on our own in each city rather than having to keep up with a guide and large group. Hilary was very sweet and gave us information about each city before exiting the bus. The winery was just a tasting experience (4 wines) with lunch. I thought they gave us a lot of food: bruschetta, meats, cheese, a full portion of pasta with ragu, and biscotti. Personally I was full after it. The employees there were very energetic and fun. Be prepared for a lot of walking. Uneven streets and hills. This tour is not…”

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Florence: Pisa, Siena, S. Gimignano, Chianti Wine & Lunch - Pisa: 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 by air-conditioned coach from Florence to Pisa, San Gimignano and Siena, with a scenic drive through Chianti. You get free time in each town, plus an optional lunch with three wines and Vin Santo. A Siena guide and cathedral entry are included only with selected options.

“Love our guide, Santo! And Paul at Siena! Very professional and informative.”

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Chianti Wine Tour from Florence - The second estate brings vineyard and cellar together
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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 the driving to a licensed tour leader on this five-hour coach trip from Florence into Chianti. Visit two organic wineries for wine, local food, vineyard and cellar tours, with a scenic ride along the Via Chiantigiana. English and Spanish tours are available. Expect some walking on slopes, and note that tasting food is not a full meal.

“Great trip, lovely guide. Super vineyards and views. Maybe an age limit would be a good idea. A small child was obviously unimpressed with the whole experience.”

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From Florence: Small Group Wine Tasting Tour to Tuscany - The first estate: cellar stories and an olive-oil taste
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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 wine estates. Expect cellar tours, roughly six wines, olive oil, and Tuscan snacks such as cheese, salami, and bruschetta. English-speaking guides, including Jason, Jonathan, and Leo on different departures, add regional stories and practical Florence tips. The route takes about four and a half hours.

“Rapha and Sergio provided a friendly and informative tour out to two Chianti wineries in a comfortable bus. The Tuscan landscape and villas dotted around the hills did not disappoint, and the wines were paired with generous antipasto plates. Great tour with fellow travellers from all over the world. Five out of five stars.”

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From Florence: San Gimignano, Siena, and Chianti Wine Tour - Siena: a quick look at a remarkable city
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From Florence: San Gimignano, Siena, and Chianti Wine Tour

15.San Gimignano, Siena, and Chianti Wine Tour

★★★★★★★★★★4.5 · 3,762 reviews · from $164

Leave Florence by air-conditioned bus or minivan for Siena, a Chianti estate, and San Gimignano. You get free time in both towns, a guided winery visit, five wine tastings, and a Tuscan meal featuring truffle lasagna, cheeses, cured meats, and more. Guides have included Marco, Lyla, and Marta, though assignments vary.

“Great experience, Lyla was a great guide. Very well coordinated and overall very fun!”

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