WINE TOURS · WINE TASTINGS IN ITALY

The 15 Wine Tastings in Italy We Would Book

191 tours  ·  from $17 a head

The 15 best wine tastings in Italy 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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Rome: Tuscany & Montepulciano Day Trip with Lunch & Wine Tasting - Montepulciano: wine town with a serious uphill walk
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Rome: Tuscany & Montepulciano Day Trip with Lunch & Wine Tasting

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

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

Spend about 12 hours touring Tuscany from Rome by air-conditioned coach. Walk through Montepulciano, visit San Biagio, eat a three-course farm lunch with wine, then browse Pienza. English-speaking guides such as Flavio, Barbara, Anna, and Antonino lead the day, with small-group upgrades adding extra tastings and a Montalcino castle visit.

“This was the best experience ever!! Beautiful countryside tour. Outstanding authentic food. Erica and Barbara were great guides. Could not have asked for a better experience”

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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

4.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

5.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

6.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

7.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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Sorrento Farm and Food Experience including Olive Oil, Limoncello, Wine tasting - Walking among Sorrento’s lemon and olive trees
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Sorrento Farm and Food Experience including Olive Oil, Limoncello, Wine tasting

8.Sorrento Farm and Food Experience including Olive Oil, Limoncello, Wine tasting

★★★★★★★★★★5.0 · 2,524 reviews · 4 hours (approx.) · from $114

Meet in central Sorrento and ride into the hills to La Masseria, a fourth-generation family farm. Guides including Eugenio and Raffaele introduce you to lemon and olive growing, animals, wine, olive oil, and limoncello before a generous farm-to-table meal. Expect walking, tastings, and a group of up to 25 people.

“All parts of the tour were fantastic. The tour guide during the walk throughout the farm was an excellent communicator. He delivered insightful information in an enjoyable manner. The food was delicious! The entire family was delightful. I highly recommend.”

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Naples: Pompeii and Mt. Vesuvius with Lunch and Wine Tasting - Pickup from Naples and the ride south
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Naples: Pompeii and Mt. Vesuvius with Lunch and Wine Tasting

9.Pompeii and Mt. Vesuvius with Lunch and Wine Tasting

★★★★★★★★★★4.5 · 2,454 reviews · from $141

Travel from Naples to Pompeii and Mount Vesuvius with guides speaking English, French, Italian, or Spanish. An archaeologist leads a two-hour Pompeii visit, followed by a local vineyard lunch and wine tasting. Finish with a crater hike or the Hell Valley lava route. Guides such as Raffaela, Giovanni, and Federica have earned praise for keeping the day friendly and well organized.

“Very fun and insightful. Lots of time at each location”

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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

10.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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Pasta Making & Wine Tasting with Dinner in Frascati from Rome - Meeting at the station and walking through the old town
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Pasta Making & Wine Tasting with Dinner in Frascati from Rome

11.Pasta Making & Wine Tasting with Dinner in Frascati from Rome

★★★★★★★★★★5.0 · 1,326 reviews · 2 hours 30 minutes (approx.) · from $45

Meet hosts such as Rosie, Niko, or Federica outside Frascati station, walk through the old town, and taste family-produced Frascati Superiore DOCG and Vagnolo wines. Then make fresh pasta with a chef, choose cacio e pepe, carbonara, or amatriciana, eat your dish for dinner, and visit the cellar caves.

“Perfect. My wife and two children (ages 9) had a wonderful experience. The town of Frascati is amazing and easy to get to from Rome via commuter train. We came in early and hung around afterwards to enjoy some food and beverage after the pasta making. From Scratch was great from the beginning. They met us at the train station, gave a quick tour of the town along with some history. We tasted a red and white wine from their vineyard, made the pasta, toured the cellar, and then we observed how to make the pasta dish itself. We also had the opportunity to purchase a bottle of wine to…”

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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

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 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

13.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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Rome: Pasta Making with Wine Tasting and Dinner in Frascati - Getting from Roma Termini to the meeting point
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Rome: Pasta Making with Wine Tasting and Dinner in Frascati

14.Pasta Making with Wine Tasting and Dinner in Frascati

★★★★★★★★★★4.9 · 979 reviews · 2.5 hours · from $35Best value

Take a 30-minute train from Rome to Frascati, where a family host such as Rosa, Rosie, Nico, or Aurora meets you at the station. Walk through town, taste two family wines with local meats and cheese, visit an old wine cave, then make fresh pasta and eat it with a Roman sauce. The class lasts 2.5 hours and costs $35.

“We had great time in this activity! We were picked up from the train station, given a short tour of the city, tasted 2 glasses of wine paired with cheese, salami and mortadella and then learned to make pasta from scratch! The host was very kind, attentive and they accomodated our food choices and intolerances with great flexibility, which we appreaciated a lot. Overally, we enjoyed it very very much!”

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Rome: Food Tour and Wine Tasting in a Traditional Trattoria - Campo de’ Fiori’s ham and cheese introduction
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Rome: Food Tour and Wine Tasting in a Traditional Trattoria

15.Food Tour and Wine Tasting in a Traditional Trattoria

★★★★★★★★★★4.7 · 962 reviews · 4 hours · from $100

Join an English-speaking guide such as Catia or Fiammetta for a four-hour food walk from Campo de’ Fiori to Trastevere. Sample fried baccalà, salami, cheeses, supplì, Roman pasta, zucchini flowers, wine, and gelato. Expect plenty of food, moderate walking, and a social group setting.

“Excellent tour. There is so much food and wine for the price of the tour. Our guide, Ferrara Flammetta Maria, was the best. She made the experience feel like we were going to dinner with friends and that's what became of us on the tour. We became friends with everyone in the group. Great experience in Rome.”

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