WINE TOURS · WINE TASTINGS IN FLORENCE

The 15 Wine Tastings in Florence We Would Book

31 tours  ·  from $33 a head

The 15 best wine tastings in Florence you can book right now, each with its price, its length and the kind of afternoon it turns into. The first one is first for a reason.

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

1.Chianti Wineries Tour with Wine Tasting

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

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

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 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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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

3.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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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

4.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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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

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 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

6.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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Half day Chianti Vineyard Escape from Florence with Wine Tastings - Meeting Piazzale Montelungo beside Santa Maria Novella
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Half day Chianti Vineyard Escape from Florence with Wine Tastings

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 in a comfortable Wi-Fi coach. Meet the winemakers, visit vineyards and cellars, taste up to eight wines with olive oil, cheese, and balsamic vinegar, then return to Piazzale Montelungo. Guides may include Alex, Lorenza, Cecilia, or Ezgi, though the guide changes by departure.

“Anna our guide was informative and very sweet. The tour was an excellent way to see the Siena area of Tuscany.”

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Tuscany Bike Tours Through the Chianti Hills with Wine Tasting - Riding Through Vineyards and Olive Groves
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Tuscany Bike Tours Through the Chianti Hills with Wine Tasting

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 guided bike ride through Chianti’s vineyards, olive groves, villas, and winding country roads. Guides such as Ben, Filippo, Angus, and Alessio lead the route, stop for photos, and help with the hills. Finish at a medieval castle with wine, olive oil, and a Tuscan lunch. E-bikes cost extra.

“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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From Florence: Val D'Orcia Tour with Wine Tasting - Montalcino and the first taste of Brunello
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From Florence: Val D’Orcia Tour with Wine Tasting

9.Val D’Orcia Tour with Wine Tasting

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

Spend 11.5 hours in Tuscany’s Val d’Orcia, visiting Montalcino, Pienza, and Montepulciano by comfortable coach. You’ll tour two wineries, taste Brunello and Vino Nobile, sample Pienza Pecorino, and enjoy free time in each hill town. Guides such as Alex, Julia, Jacob, and Constantino are praised for clear explanations and useful local tips.

“The whole day was fantastic. It was a well-organized trip to Tuscany, and we had plenty of free time. Thank you :)”

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From Florence: Chianti Hills Half-Day Tour with Wine Tasting - Walking through the vines and learning the basics
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From Florence: Chianti Hills Half-Day Tour with Wine Tasting

10.Chianti Hills Half-Day Tour with Wine Tasting

★★★★★★★★★★4.5 · 703 reviews · 5 hours · from $48

Travel by air-conditioned Gran Turismo bus from Santa Maria Novella station to Chianti, where you walk among vines, visit a vinegar cellar, taste seven wines, vin santo, olive oils, cheeses, cold cuts, and seasonal Tuscan specialties. Guides such as Chiara, Emma, and Jordano have led recent departures, but staff can vary.

“We had a great experience. Thanks to our wonderful guide Chiara who told us important facts about the region and everything you need to know about Tuscan wine. She cared a lot about the wellbeing of the whole group for the trip and went above and beyond to make it perfect for everyone. Our driver Toto was also very skilled and we had a safe and relaxed bus journey. You can consider yourself lucky when you are making this tour with them!”

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Tuscany Experience: Pisa, Siena, San Gimignano & Wine Tasting - Pisa and the Piazza dei Miracoli
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Tuscany Experience: Pisa, Siena, San Gimignano & Wine Tasting

11.Tuscany Experience: Pisa, Siena, San Gimignano & Wine Tasting

★★★★★★★★★★4.5 · 653 reviews · 11 hours 30 minutes (approx.) · from $53

Leave Florence at 7:30 a.m. for Pisa, San Gimignano, Siena, and a Chianti winery lunch with three wine tastings. Choose classic guided service or transfer-only transport, and add the Leaning Tower climb if available. Guides such as Barbara, Vanessa, and Niccolò have earned strong praise, but the group can reach 60 people.

“The tour guide could’ve have been a little more informative of the history. Communication was an issue.”

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Tuscany Vespa Tour: Lunch & Wine Tasting, Countryside Roads - Riding through vineyards, olive groves, and hill roads
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Tuscany Vespa Tour: Lunch & Wine Tasting, Countryside Roads

12.Tuscany Vespa Tour: Lunch & Wine Tasting, Countryside Roads

★★★★★★★★★★5.0 · 614 reviews · 5 hours (approx.) · from $228

Leave Florence by air-conditioned minivan with guides such as Luca, Alexa, or Dejan, learn to handle an automatic Vespa, and ride through Chianti’s hills, vineyards, and olive groves. Finish at a family-run winery with a cellar visit, wine tasting, olive oil, and a traditional lunch. Riders who lack confidence can ride as passengers.

“Great experience. Nice to get out of busy city and see countryside on a Vespa. Small winery from 1300s, very friendly staff. Luca was fantastic! Highly recommend this experience.”

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Florence: Countryside Tour with Wine Tasting & Pasta Class - The 45-minute ride from Florence to Fucecchio
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Florence: Countryside Tour with Wine Tasting & Pasta Class

13.Countryside Tour with Wine Tasting & Pasta Class

★★★★★★★★★★4.9 · 546 reviews · 7 hours · from $71

Leave Florence for a family-run organic farm in Fucecchio, where guides such as Christina, Naomi, and Noemi lead a vineyard and botanical garden walk, cellar tasting, and fresh pasta class. Expect five wines, local snacks, lunch or dinner, farm animals, and a warm, social setting for up to 20 people.

“It was amazing! Delicious drinks and food, highlight of my trip.”

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Tuscany Vespa Tour from Florence with Wine Tasting - Learning to ride before the Tuscan roads
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Tuscany Vespa Tour from Florence with Wine Tasting

14.Tuscany Vespa Tour from Florence with Wine Tasting

★★★★★★★★★★5.0 · 425 reviews · 7 to 8 hours (approx.) · from $241

Spend 7 to 8 hours riding a Vespa through the Tuscan hills, visiting medieval San Gimignano, and sharing a local winery lunch with Chianti pairings. Guides such as Daniel, Cecilia, Marco, and Daniele help you practice, stay safe, and enjoy the day. Drivers need an original license and must be at least 18.

“The Vespa tour with Max & Daniel was even BETTER THAN EXPECTED. WOW the views in the Tuscany countryside will leave you breathless. San Gimignano is one of a kind with St. Matthew & St. John’s gates. The dining experience was over the top incredible with personable Italian family hospitality. Barcelona Vibes Max & Daniel!!! LOL”

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Florence: Val d’Orcia Wine Tasting & Lunch Small Group Tour - Montepulciano: a hill town with wine below the streets
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Florence: Val d’Orcia Wine Tasting & Lunch Small Group Tour

15.Val d’Orcia Wine Tasting & Lunch Small Group Tour

★★★★★★★★★★4.3 · 352 reviews · 12.5 hours · from $111

Spend a full day beyond Florence with an English, Spanish, or Italian-speaking guide. Visit Montepulciano, Pienza, and Montalcino, taste Rosso and Vino Nobile wines, sample olive oil and Tuscan snacks, and enjoy lunch with cured meats, cheese, pasta, water, and coffee. Guides such as Marco and Luca have earned praise for their warmth and local insight.

“Very fun tour, beautiful countryside, great winery! Guides were knowledgeable and kind. Bus driver did a great job as well. Only down fall, no public restrooms, sometimes need to pay to use facilities.”

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