The 10 Best Wine Tasting Tours in Florence

1.Chianti Wineries Tour with Wine Tasting

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

Travel by comfortable coach from Florence to two Chianti wineries for guided tastings, vineyard walks, and samples of cheese, salami, bread, olive oil, and balsamic vinegar. Guides such as Anna, Alex, Martina, and John have been praised for bringing Tuscany’s wine, villages, and farming traditions to life. Expect about 5 to 5.5 hours, with no hotel pickup or lunch.

“The tour was great. We had first a visit to a traditional small vineyard from a Italian family, great wine and food, and the Nona was super nice with us. We saw the grapes plantations, drank wine and they were good and had snacks. Second one was way bigger, so more comercial, but it was super cool to see the difference between them, specially cause the second one was more than 100years old. The guide knew a lot about the region, and she even gave us recommendations about Florence. Everything went well”

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

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

From Santa Maria Novella, ride into Chianti with an English-speaking guide such as Leo, Jonathan, or Matteo. Visit two wineries, taste six or more regional wines, sample olive oil and Tuscan specialties, and compare estates, cellars, and winemaking styles. The roughly 4-hour-45-minute trip gives you countryside time without consuming a full day.

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

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

Ride from central Florence in an air-conditioned 4x4 with an English-speaking sommelier. Choose a 7-hour Chianti outing, a sunset dinner, or longer routes to Brunello and Montepulciano. Expect family wineries, cellar visits, olive oil, salumi, cheese, pasta, and generous countryside views.

“Guide was informative and fun. The wines were good as was the food served. The grounds and estate were lovely. Met lovely people from across the world and had great conversations. Only adults on this tour but they were of all ages. Highly recommend”

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

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

Spend 11 hours touring Tuscany by coach, with free time in San Gimignano and Monteriggioni, a Chianti winery lunch and tasting, and guided Siena options. Guides such as Sandro, Marta, Ricardo, and Ilaria have earned praise for clear, friendly leadership. Choose the cathedral upgrade if Siena art matters to you.

“Beautiful towns, gorgeous food and lovely hosts! The tour started on time and it was well organised. The bus was very comfortable with free wifi and plugs for you to charge your phones. Our hosts were very accommodating and attentive to our needs. Many thanks to AARON and LILY for being our guide and to PLACIDO for driving us to our destinations safely.”

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5.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 wineries. You will taste six wines, olive oils, cheese, salami, cold cuts, and bruschetta while local hosts explain cellar methods and Tuscan traditions. Guides such as Jason, Jonathan, Leo, and Raffaele are known for lively commentary, music, and practical Florence tips.

“This was a great relaxing evening. This is a nice tour for when you need a break from the museums and running to different spots. Although more insight into the wine making process would have been great, we knew what we signed up for. The wine was delicious, but we took away a new appreciation of really good aged local balsamic. It was terrific with the Pecorino cheeses and paired nicely with the classicos. Highly recommend!”

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

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

From Florence, ride through the Tuscan countryside to San Gimignano, a Chianti winery, Siena, and seasonal Monteriggioni. You get free time, local guides, three wines, Vin Santo, and a three-course lunch. Guides such as Marta, Ricardo, Sandro, and Alessandra are praised for clear directions and good humor, though Siena time can feel short.

“The trip was great! A very easy day out without feeling rushed or feeling like travel time was long. Coach was comfortable and ride was smooth. Guide Hilary was professional, yet enthusiastic. Lunch and wine at vineyard was excellent. before the trip i was a little fearful due to long duration. but i thoroughly enjoyed myself and wished did not end :)”

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7.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 up to six to eight wines with olive oil, cheese, and balsamic vinegar, and tour vineyards and cellars. Guides such as Alex, Lorenza, and Cecilia have earned praise for clear, friendly explanations, though the group may reach 43 people.

“The wine tour was very fun and informative! A nice bus ride through Tuscany and an experience of two different wineries. Both places were very accommodating and the wine & additional tasty treats were very good. We had a nice sunny cool day in December and the scenery was beautiful!”

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

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

Leave Florence by van for a roughly 12-mile ride through Chianti’s vineyards, olive groves, villas, and country roads. Guides including Ben, Filippo, Angus, and Alessio lead the route, with photo stops, a castle wine tour, olive oil tasting, and Tuscan lunch. Regular bikes are included. E-bikes cost extra and require advance notice.

“After check in at the meeting point, we started with a short van ride to the castle where we were outfitted with well maintained bikes, helmets and water bottles. Ben was a great guide and Lorenzo was great support. We had a good mix of skill levels and all did well. The winery tour at the castle along with the food and wine were very nice at the end. pro tips: - take the bio break before you leave the meeting place as the next one available is after the ride - if you're not a regular cyclist and want to complete the entire ride, consider the e-bike option to…”

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9.Val D’Orcia Tour with Wine Tasting

★★★★★★★★★★4.6 · 1,106 reviews · 11.5 hours · from $108

Spend 11.5 hours in Tuscany with a guide such as Alex, Julia, or Constantino, visiting Montalcino, Pienza, and Montepulciano. Ride a comfortable coach, tour two wineries, taste Brunello and Vino Nobile, sample Pienza’s Pecorino, and enjoy free time for lunch, photos, and wandering. Expect hills, stairs, and a full day.

“We loved the whole day trip to the wineries and the Tuscan towns of Montelcino, Pienza and Montepulciano. Pienza was definitely a high light town for us. We hoped there were more wineries to visit but the ones we did see were lovely!”

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10.Chianti Vineyards Escape from Florence with Two Wine Tastings

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

Travel by Wi-Fi-equipped coach from Florence to two Chianti estates, with cellar visits, vineyard walks, and several wine tastings paired with cheese, salami, olive oil, and balsamic vinegar. Guides such as Margherita, Anna, Emma, and Alex have drawn praise for their warmth. Expect a large group, a brisk schedule, and time to shop.

“The tour was perfect. The driving time was manageable, the views were beautiful, and the food was good.”

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