Tastings · WINE TASTING TOURS IN ITALY

The 15 Best Wine Tasting Tours in Italy

38 tours  ·  from $25 a head

The 15 best wine tasting tours in Italy to book here, with what each pours, what it costs and how much of the day it takes. Number one is at the top for a reason; start there.

Florence: Chianti Wineries Tour with Wine Tasting - Meeting the coach near Santa Maria Novella
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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 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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Small-Group Wine Tasting Experience in the Tuscan Countryside - The second estate: more wine and a Tuscan table
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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, 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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Rome: Tuscany & Montepulciano Day Trip with Lunch & Wine Tasting - San Biagio and the best church view
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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 traveling from central Rome to Montepulciano, San Biagio, a Tuscan farm, and UNESCO-listed Pienza. You’ll get a guided town walk, three-course lunch, regional wines, and free time for pecorino, gelato, and photos. Guides vary, with Flavio, Anna, Barbara, Antonino, and Sonia among the praised names.

“I really enjoyed this day tour of Tuscany from Rome. Our guide Antonino was great and knowledgeable. The tour first stopped in Montepulciano which was my favorite. Unfortunately, I felt visiting Montepulciano was rushed, we didn't have much time to explore on our own. We then stopped for lunch, I agree with others, we just got small splashes of wine to try and the food was kind of underwhelming. We stopped in Pienza as well which was beautiful. Unfortunately, the day I was there, everything was closed. There was not much to do. My recommendation is give us more time in Montepulciano and less time in Pienza. Otherwise, I really…”

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SMALL-GROUP Wine Safaris: Tuscan Wine Tasting Tours from Florence - Wine tasting, explained without the lecture
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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

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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San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch & Wine Tasting - San Gimignano and the town of towers
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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 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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From Florence: Small Group Wine Tasting Tour to Tuscany - The first winery: wine, olive oil, and cellar traditions
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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 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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Florence: S. Gimignano, Siena, Chianti Wine Tasting & Lunch - A Chianti winery lunch with local wine
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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

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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Sorrento Farm and Food Experience including Olive Oil, Limoncello, Wine tasting - Walking through lemons, olives, and farm animals
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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. Walk among lemon and olive trees, learn how the family makes oil and limoncello, taste honey, cheese, marmalade, and wine, then sit down to a farm-to-table meal. Eugenio, Eugene, or Raffaele may lead the visit.

“The information about the farm was great and informative. It was amazing to see the many things the family does on their own at the farm. They were very personable, funny, communicative for pickup, accommodating and provided a really nice meal. We were also able to buy some of their products before we left at reasonable prices. We met some really nice people we dined with at our table. It was tough for only one thing and that was that it was rainy and windy. We enjoyed it immensely anyway. One last thing...I lost my water bottle from my backpack and they reached me the very next day to let…”

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Naples: Pompeii and Mt. Vesuvius with Lunch and Wine Tasting - Pickup points 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

Spend a full day with Worldtours visiting Pompeii with an archaeologist, eating a traditional lunch at a local vineyard, and hiking Mount Vesuvius. Guides such as Federica, Giovanni, and Raffaella have earned praise for clear, lively hosting. Choose the crater trail or, if weather closes the summit, the Valley of Hell lava route.

“This day trip was the highlight for my time in Naples by far. Raffaella was a great guide and very friendly and the driver with her(sorry I forgot his name) was great. If you can, go with the wine tasting and lunch. Worth every penny and the lunch spot has an incredible view”

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Half day Chianti Vineyard Escape from Florence with Wine Tastings - Piazzale Montelungo and the 40-minute ride south
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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 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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Pasta Making & Wine Tasting with Dinner in Frascati from Rome - Meeting the hosts and entering the family cellar
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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, Nico, or Federica at Frascati station, walk through the old town, taste family-produced wines, and make cacio e pepe, carbonara, or amatriciana with a chef. You’ll eat your pasta at dinner, tour the cellar caves, and return to the station. English instruction, small groups, and dietary options are available.

“We loved being guided by Federica and we were lucky to be part of a great group. Delicious wine and pasta was one of the best we had ever had, made with our hands. Thank you for the experience!”

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Tuscany Bike Tours Through the Chianti Hills with Wine Tasting - The one-mile hill you need to plan for
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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 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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Rome: E-Bike Night Tour with Food and Wine Tasting - Starting near Santa Maria Maggiore
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Rome: E-Bike Night Tour with Food and Wine Tasting

13.E-Bike Night Tour with Food and Wine Tasting

★★★★★★★★★★4.9 · 1,131 reviews · from $89

Ride through Rome with a guide such as Adriana, Elis, Bruno, or Felipe, stopping at major sights from Saint Peter’s Square to the Trevi Fountain. You’ll practice on the e-bike, ride in a group of up to eight, and pause at a Roman salumeria for cold cuts, cheese, and wine. The four-hour route ends back near Santa Maria Maggiore.

“Great experience! Our Tour guide Felipe went above and beyond on the journey! Very knowledgeable on everything and explained every single thing to the detail. All the sites that we visited looked spectacular. I truly recommend these guys! They are awesome.”

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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

14.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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Rome: Pasta Making with Wine Tasting and Dinner in Frascati - Inside the family wine cellar
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Rome: Pasta Making with Wine Tasting and Dinner in Frascati

15.Pasta Making with Wine Tasting and Dinner in Frascati

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

Take a 30-minute train from Roma Termini to Frascati, where a local family collects you for a short town walk, two wine tastings, snacks, and hands-on pasta making. In a 15th-century cellar, you’ll prepare fresh pasta, choose a Roman sauce such as Carbonara or Cacio e Pepe, then eat your creation before visiting the old wine cave.

“Started with wine tasting and history about the wine, then we made the pasta and they made us a dish with the pasta we made! Was very very good! Highly recommend”

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Just poured: Wine Tasting Tours in Italy

★ 5.0A Venetian Evening: Wine Tasting and Cicchetti with a Local GuideFrom $131146 reviews
★ 4.0Private Secret Venice Tour; Rialto Market, San Polo & Food and Wine tastingFrom $257220 reviews
★ 4.5Chianti Vineyards Escape from Florence with Two Wine TastingsFrom $53280 reviews
★ 4.8Verona: Wine Tasting with Snacks and Panoramic ViewsFrom $53494 reviews
★ 4.5Discover Valpolicella Vineyards and Wine Tasting ExperienceFrom $84341 reviews
★ 5.0Amarone Wine-tasting Tour from Verona with Private TransportationFrom $151283 reviews
★ 4.9From Verona: Valpolicella and Amarone Wine Tasting TourFrom $112560 reviews
★ 4.7The Turin Chocolate & Wine Tasting ExperienceFrom $8187 reviews
★ 4.7Etna: Wine Tasting and Food TourFrom $129201 reviews
★ 4.5Visit Best Wineries in Tuscany – Wine Tasting & TourFrom $47263 reviews
★ 4.7San Gimignano: Lunch or Dinner at a Winery with Wine TastingFrom $65177 reviews
★ 4.9Prosecco Hills and Wine Tasting TourFrom $153357 reviews
★ 4.5Wine Tasting Tour on Vesuvius Slopes with Lunch330 reviews
★ 4.6Wine Tasting & Lunch in a Typical WineryFrom $65183 reviews
★ 4.8Wine Tasting and Cellar TourFrom $38545 reviews

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