The 15 Best Wine Tours in Italy

Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery - Siena Cathedral deserves your attention

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

See Siena, San Gimignano, Pisa, and Chianti in one full Tuscan day, with Siena Cathedral, winery lunch, wine tasting, and free time.

“Great day trip, would definitely recommend. So much was crammed into the day. Requires a little bit of walking, nothing too strenuous. Great value for money. Annalise the tour guide in Siena was brilliant. Our walkabout tour guide “Ginni” was extremely friendly and informative. Coach driver “Emi” was also great. Great itenary to ensure so much is included but never felt rushed.”

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

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

★★★★★★★★★★4.5 · 8,393 reviews · 12 hours · from $52Best value

Review of a 12-hour Tuscany day trip from Florence to Pisa, San Gimignano, Siena, and Chianti, with wine, lunch, and practical tips.

“I enjoyed every moment of this tour. Barbara is an amazing guide and told us everything about the places we visited and where to find the best gelato and coffee (and bathrooms😅). For the Siena tour, Chiara was an amazing tour guide and the lunch at Poggio Ai Laghi was paired with some of the best wines I tasted. The whole tour was an amazing experience and I recommend it to anyone who wants to see the highlights, just so they can visit those places by themselves again and fully enjoy everything about Toscana.”

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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

Visit two Chianti wineries from Florence, taste up to seven wines with Tuscan snacks, and enjoy rolling vineyard views on this half-day tour.

“We really enjoyed our visit to the two wineries as part of this tour. The tour guide was really friendly and so were the two guides who led the visits to the wineries. The bus transportation was really comfortable, however the drive out to the first winery was around an hour and 15 minutes. Additionally, its important to note that as the Chianti wine region is known for red wines, that will be the majority of the wines tasted at both wineries.”

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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

Visit two Chianti wineries from Florence, taste six wines with olive oil and Tuscan specialties, and enjoy a scenic half-day in the hills.

“Tour guide is very professional. Each of the two wineries provided four different wines for tasting. Couple of the wines are made with grapes that you can only find either in their vineyards or in that region.”

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Rome: Tuscany & Montepulciano Day Trip with Lunch & Wine Tasting

5.Tuscany & Montepulciano Day Trip with Lunch & Wine Tasting

★★★★★★★★★★4.5 · 5,232 reviews · 12 hours (approx.) · from $83

Review of Rome’s Tuscany and Montepulciano day trip, with hill towns, farm lunch, wine tasting, Pienza, transport, costs, and practical tips.

“The tour guide Barbara and our wonderful driver made the day informative, safe and fun. Thank you for an unforgettable adventure.”

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

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

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

Explore Tuscany from Florence by 4x4, with private wineries, Chianti or Brunello tastings, local food, and sweeping vineyard views.

“WeI had the most amazing time on this wine tour! The vineyards were beautiful and the experience itself was so much fun, but what truly made it unforgettable was our guide, Sara. She was absolutely phenomenal—so knowledgeable, engaging, and genuinely hilarious. Sara had the perfect balance of expertise and personality. She explained everything in such an interesting way, answered every question with ease, and kept us laughing. Her energy made the whole tour feel special, and I can honestly say she turned a great experience into an exceptional one. She even helped practice my Italian! I would 100% come back and book this tour again specifically if Sara were the…”

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Winner 2025 Florence Sunset Food & Wine Tour by Eating Europe

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

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

Florence sunset food and wine tour review covering wine windows, Tuscan dishes, Negroni, gelato, guides, value, and practical tips.

“This food and wine tasting walking tour in Florence, on the other side of Arno River, in Oltrarno, guided by Assia, was an emotional and very inspiring experience that I would highly recommend to everyone who loves good food and wine and is eager to learn more about the history and culture of the region”

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

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

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

See Siena, San Gimignano, Pisa, and Chianti on a full-day Florence tour with guided visits, Tuscan lunch, wine, and comfortable transport.

“The guide was great, she explained each detail about our day trip. she didn't miss any detail about us, the group at each stop. we had a nice lunch, everything was great, we all enjoyed Sienna, Chianti and Pisa. A well recommended trip!”

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

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

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

Explore San Gimignano, Siena, Monteriggioni, and Chianti from Florence with lunch, three wines, and practical tips on value and pacing.

“Provided food & wine weren’t so memorable, yet overall day trip experience was a very good value. Our guide was absolutely outstanding when a family member needed unexpected attention.”

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

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

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

Review of a 12-hour Tuscany tour from Florence to Pisa, San Gimignano, Siena, and Chianti with transport, lunch, and wine options.

“Well organized and we had a wonderful time! Martha our tourist guide is very knowledgeable and gave us clear instructions and helpful tips to make our trip seamless. Our driver Silvio has been great as well and drove us all safely to all our destinations.”

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Chianti Wine Tour from Florence

11.Chianti Wine Tour from Florence

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

Review of the 5-hour Chianti wine tour from Florence, with two organic wineries, Tuscan food, scenic views, practical tips, and honest drawbacks.

“It was informative and beautiful sites. Both places were so nice. The wine was also very good. Lovely places.”

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From Florence: Small Group Wine Tasting Tour to Tuscany

12.Small Group Wine Tasting Tour to Tuscany

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

Taste six Tuscan wines, olive oils, cheese, and salami at two Chianti estates on a relaxed half-day trip from Florence.

“Leo was a lovely and knowledgeable tour guide. We felt well taken care of and the wineries we visited were fantastic! The small group size made for an especially convivial and intimate experience.”

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From Florence: San Gimignano, Siena, and Chianti Wine Tour

13.San Gimignano, Siena, and Chianti Wine Tour

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

Explore Siena, Chianti, and San Gimignano from Florence with wine tasting, Tuscan lunch, medieval towns, and free time.

“Marco our tour guide was amazing! He was very knowledgeable and explained everything clearly. He also made sure to talk and connect with many of the people on the tour individually, so it felt very personalized! The tour itself was also incredible - being able to see all the beautiful areas that I did in one day? 10/10”

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Rome Food Tour: Unlimited Tastings with Fine Wine & Barolo

14.Rome Food Tour: Unlimited Tastings with Fine Wine & Barolo

★★★★★★★★★★5.0 · 3,365 reviews · 4 hours (approx.) · from $83

Taste up to 20 Roman foods, fine wines, pizza, pasta, truffles, and gelato on a four-hour small-group tour in Prati.

“Michael was a great host and very knowledgeable as well as entertaining. Sampled some grat food and amazing wines - highly recommended!”

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Siena, San Gimignano and Chianti Wines Day Tour from Florence

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

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

See Siena, San Gimignano, Monteriggioni, and Chianti from Florence on a long, well-organized day tour with wine tasting and free time.

“Great trip. We were a lot (double decker bus). Siena was great. Had to hurry if you do cathedral inside and panoramic view. Wine was fun. And San Gimignano was cute. Siena def was the highlight. Probably would have skipped the first stop to have more time at the other stops.”

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