Italy · WINE TOURS IN FLORENCE

15 Wine Tours in Florence Worth Booking

34 tours  ·  from $37 a head

Good wine tours in Florence fill up weeks ahead and the great ones go first. Below: the 15 to book early, what each includes and how they differ.

Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery - Starting at Santa Maria Novella Station
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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 highlights, free time in San Gimignano and Pisa, and an optional farmhouse lunch with four wine tastings. Guides such as Sara, Davide, Alex, and Manolo are praised for keeping this busy day clear, friendly, and on schedule.

“Manolo and his team took great care of us and were so knowledgeable about all the places we went to. The sights were fabulous and the winery was absolutely exceptional! We had plenty of free time to explore, buy some souvenirs and make life long memories.”

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Florence: Chianti Wineries Tour with Wine Tasting - The first hour: Florence to the Chianti Hills
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Florence: Chianti Wineries Tour with Wine Tasting

2.Chianti Wineries Tour with Wine Tasting

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

Leave Florence by comfortable coach for two Chianti wineries. You’ll tour vineyards and cellars, taste three to four wines at each stop, and sample cheese, salami, bread, olive oil, and balsamic vinegar. Guides such as Martina, Cecilia, and Constantino have helped make this half-day outing lively, though group sizes can be large and food portions are light.

“Both wineries we visited were beautiful and the hosts were joyful and hospitable. Our guide shared interesting information about the wine region; she was cheerful and kind. The bus ride gave us scenic views of the area. What a great experience! We absolutely loved it. Our favorite thing, besides the great wine, was meeting guests on our tour from all over the world.”

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Small-Group Wine Tasting Experience in the Tuscan Countryside - First estate: vineyard, cellar, and three wines
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Small-Group Wine Tasting Experience in the Tuscan Countryside

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

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

Leave Florence from Santa Maria Novella station for two Chianti Classico wineries. Tour vineyards and cellars, taste six or more regional wines, and sample olive oil, cheese, salami, cured ham, and bruschetta. Guides such as Leo, Matteo, Jonathan, and Leonardo add local history and practical wine tips.

“Do it, such a great experience and great tour guide. So fun and the perfect amount of time, and great value.”

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SMALL-GROUP Wine Safaris: Tuscan Wine Tasting Tours from Florence - Choosing between Chianti and Val d’Orcia
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SMALL-GROUP Wine Safaris: Tuscan Wine Tasting Tours from Florence

4.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 for a 4x4 wine safari through Chianti or Val d’Orcia. With an English-speaking sommelier guide such as Ginevra, Sara, or Alex, you’ll visit family wineries, taste wine, olive oil, cheese, and salumi, and share a Tuscan lunch or dinner. Choose a 7-hour half-day option or a longer full-day route.

“What an amazing experience, our tour guide Ginebra “Ginny” is exceptional, educated, very informative and passionate about the art of wine making. The locations that are part of this tours are breathtaking, the wine was some of the best wines I have tasted and the driver Christophe is an excellent driver. I can ramble on about the driver, tour guide, vineyards and restaurant .. just understand that this experience is a must.”

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Winner 2025 Florence Sunset Food & Wine Tour by Eating Europe - DiVin Boccone brings wine and charcuterie into an old cellar
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Winner 2025 Florence Sunset Food & Wine Tour by Eating Europe

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

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

Spend an evening crossing Florence’s Oltrarno neighborhood with a local English-speaking guide such as Antonella, Dimitri, Sara D., or Martino. You’ll visit small food shops, historic trattorias, and two wine windows while tasting Prosecco, Tuscan wines, cheese, pasta, soup, wild boar stew, a Negroni, and artisan gelato. The group is limited to 13 people.

“Eli was fantastic. She guided us on a wonderful food and wine journey through Florence. Her knowledge and passion elevated the experience providing unique insights and history. Highly recommend!”

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From Florence: Siena, San Gimignano, Pisa & Lunch at Winery - Siena: Gothic stone, yellow walls, and Piazza del Campo
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From Florence: Siena, San Gimignano, Pisa & Lunch at Winery

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

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

Travel from Florence by comfortable coach to Siena, San Gimignano, Chianti, and Pisa. You’ll tour Siena with a local guide, visit the Gothic cathedral, enjoy an optional farmhouse lunch with four Tuscan wines, and finish at the Leaning Tower. Guides such as Sara, Alessandro, and Manolo are known for keeping the long day lively and well organized.

“It was convenient and comfortable. On time for drop and pick up. The guide was really good. Especially, a boat tour was good for us. Driving was safe. The driver was wonderful.”

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San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch & Wine Tasting - Monteriggioni: a small fortress with a short visit
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San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch & Wine Tasting

7.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 three-course winery lunch, three Chianti wines, and Siena sightseeing. Select the Siena guide and cathedral upgrade for a fuller visit. Guides such as Sandro, Marta, Ricardo, and Ilaria are praised for clear, friendly service.

“Sandro and Fabi were fantastic, well organised and very informative. Great meal and wine tasting too! Even the rain couldn't dampen the mood.”

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Chianti Wine Tour from Florence - Riding the Via Chiantigiana into the hills
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Chianti Wine Tour from Florence

8.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. You’ll taste six or seven Tuscan wines, sample cheese, salami, bruschetta, olive oil, and balsamic vinegar, and tour vineyards and cellars with local hosts. Guides such as Aaron, Cristina, Alessandra, and Maria Luisa have helped make this five-hour outing especially engaging.

“Both wineries were amazing! Lots of Knowledge about making the wine and very personal wanted you to ask questions and just talked to you during the tour. Tommas from the second location super friendly and did an excellent job! Both shipped to the US and you could buy another glass while you walked around the site. Both had some snacks at the venues, but would eat lunch or dinner before going.”

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From Florence: Small Group Wine Tasting Tour to Tuscany - The first estate, cellar traditions and three wines
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From Florence: Small Group Wine Tasting Tour to Tuscany

9.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. Taste about six wines and local olive oils with cheese, salami, cold cuts, and bruschetta. English-speaking guides such as Jason, Leo, Jonathan, and Raffaele have helped make this a lively, social outing, though the wineries and guide can vary.

“This tour was incredible from start to finish! The scenery was breathtaking. The wine tasting was fantastic, with a great selection of local wines that were both delicious and unique. Our guide was friendly, knowledgeable, and made the whole experience even more enjoyable with interesting stories and insights about the region. Everything was perfectly organized and relaxed. We couldn’t have asked for a better day — highly recommend this tour to anyone visiting Tuscany! 🍷🌻🇮🇹”

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Florence: S. Gimignano, Siena, Chianti & Wine Tasting Lunch - San Gimignano: two hours among the towers
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Florence: S. Gimignano, Siena, Chianti & Wine Tasting Lunch

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

★★★★★★★★★★4.6 · 2,427 reviews · from $89

Travel from Florence by air-conditioned coach to San Gimignano, Monteriggioni, Siena, and a Chianti winery. You get free time in San Gimignano, a three-course lunch with three wines, and an optional guided Siena Cathedral visit. English and Spanish tours are available, with guides such as Marta, Aaron, Ricardo, and Sara leading some departures.

“Our tour guide Aaron was the best! Can’t really ask more.”

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Half day Chianti Vineyard Escape from Florence with Wine Tastings - Cellars, vineyards, and the winemaking lesson
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Half day Chianti Vineyard Escape from Florence with Wine Tastings

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

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

Ride from Florence to Chianti in a comfortable Wi-Fi coach, then visit two wine estates for cellar and vineyard walks, 3 to 4 tastings at each, olive oil, cheese, balsamic vinegar, and Tuscan snacks. Guides such as Alex, Lorenza, Anna, and Cecilia have led recent departures. Expect a friendly, social group rather than a private wine lesson.

“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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Tuscany Bike Tours Through the Chianti Hills with Wine Tasting - Two hours through vineyards and olive groves
Chianti & Tuscan Countryside Tours, Cycling Tours, Food & Drink, Tour Reviews, Tours, Tours in Florence, Wine Tours, Wine Tours in Florence

Tuscany Bike Tours Through the Chianti Hills with Wine Tasting

12.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 guided two-hour ride through Chianti’s vineyards, olive groves, villas, and country roads. Guides including Ben, Filippo, Angus, and Alessio lead the route, with a support van for the steepest hill. Finish at a medieval castle with wine, olive oil, and a Tuscan lunch.

“Great from start to finish-a fun ride with stunning views and Ben was an informative, energetic and fun guide!”

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From Florence: Chianti Wine Tour with Tastings - Leaving Florence for the Chianti hills
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From Florence: Chianti Wine Tour with Tastings

13.Chianti Wine Tour with Tastings

★★★★★★★★★★4.4 · 1,025 reviews · from $62

Spend five hours in the Chianti hills with an English or Spanish-speaking guide, visiting two organic family wineries. Tour old cellars, walk among vineyards, taste three or four wines at each stop, and sample pecorino and other Tuscan foods. Guides such as Aaron, Alessia, Vera, and Keiko have been praised for lively commentary.

“One of my favorite parts of my trip to Florence! All the guides were super amazing, and the views were lovely.”

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Tuscany Wine Tour: 2 Wineries & San Gimignano from Florence - First winery: a generous introduction to Tuscan wine
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Tuscany Wine Tour: 2 Wineries & San Gimignano from Florence

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

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

Spend about seven hours in Tuscany with a local guide such as Emanuele, Valentina, or Giovanni. Ride from Florence to two wineries for wine, olive oil, balsamic vinegar, and regional bites, then enjoy 90 minutes in San Gimignano. The adult-only minibus tour includes eight wine tastings and returns to Florence around 5pm.

“Ottavio guided a perfect day in Tuscany as we visited two wineries and the walled town of San Gimignano. On the drive from Florence, Ottavio kept us entertained with both personal stories of growing up in Tuscany and the history of the region. We could NOT have asked for a better experience or guide.”

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Chianti Wineries Tour with Tuscan Lunch and San Gimignano - The first winery: a personal introduction to Chianti
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Chianti Wineries Tour with Tuscan Lunch and San Gimignano

15.Chianti Wineries Tour with Tuscan Lunch and San Gimignano

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

Spend about eight hours with a small group of up to 16, visiting two Chianti wineries, tasting local wines, eating a Tuscan lunch, and exploring San Gimignano. Guides such as Lorenzo, Daniel, Christian, Cecilia, Max, and Leonardo add local stories, music, and practical help. Round-trip transport leaves central Florence at 9 a.m.

“This was part of an end of life trip for me (stage 4 cancer) with my two adult daughters and my oldest daughter’s husband. We are traveling to Venice, Florence, Rome, Catania, Sorrento, Naples. I love wine and wineries and so this was probably the excursion I was most looking forward to. Tour guide was great. First winery—very dynamic host and good wine. 2nd winery-not as personal, great lunch, but not great wine. Trip to San Gimignan beautiful and fun but felt rushed. Driver said he would take my daughter back after last winery to the place that specializes in tiramisu but he did not. Overall good-but we enjoyed the…”

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